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Surrogate

Like you, my wife has quit putting out. And she’s only 47 years old. Dang!

Well anyway, a week before my 48th birthday, she asked what I wanted.

I immediately said, “Sex.”

She got all huffy, then settled down, explaining for the millionth time, it was her ‘hormones.’

Whatever, right?

Then she asked, “What if I get you a surrogate?”

“You mean like a whore?”

“No, not at all. Maybe like a proper sex worker, or a therapist or something?”

We both fell silent, because even though the idea was certainly attractive, I couldn’t imagine any practical way it could work.

The discussion was forgotten. A week later, on the evening of my birthday, our niece LuLu was over for dinner. I was almost sullen. So far, my birthday had been uneventful, and the last thing I wanted to do was to have to sit down to dinner with this young girl with whom I had nothing in common other than her course of study.

She did seem more bubbly and sparkly-eyed than normal, which is saying a lot for her. She’s thin and naturally active, almost hyper-active.

We talked about her schooling. She was studying to be a psychologist. I felt honored in a way, because that is my profession, and I liked to think part of her decision to pursue psychology was due to me.

Then she floored me by announcing that she was planning to focus on sexuality. I almost choked on my bite of potato.

In her non-stop, active way, without hardly taking a breath, she went on to say that she’s a big advocate of sex as a way to heal many of society’s ills, and especially personal ills. She clarified, saying masturbation was one of the best outlets a person can allow themselves, and went on to expound on the benefits of wanking.

Despite our age difference, and my wife sitting right there with us, I became fascinated. And, I can admit, I felt a stirring in my pants, as I was imagining this young woman involved in the activities she was describing. Obviously, she must masturbate frequently, since that’s such a strong part of her belief system.

As I was pondering that, and LuLu stopped for an odd moment, my wife interjected, “So you like to masturbate a lot?”

“Oh, yes,” she freely admitted.

My wife didn’t stop there. Turning to me, “And you masturbate quite a bit too, don’t you?”

Geez! That was embarrassing. How does one answer that? But, figuring how forthcoming LuLu was being, I went ahead and admitted that I do wank quite a bit.

The conversation intensified, until finally, with my wife’s help, LuLu had us engaged in a game of strip poker. But it was just her and I. My wife then went into the den to watch TV or something.

I was naked first. Although embarrassed in a way, I was becoming OK with the fact that I was displaying an obvious erection to this young girl. Looking at those luscious tits, how could I resist?

I didn’t know where this was going, but of course I caught on early that it was my birthday, and this, being here with LuLu, was somehow my wife’s present to me. Furthermore, there was so much talk of masturbation that I pretty much knew I wouldn’t be fucking LuLu. Frankly, as pretty as she was, I didn’t really want to. But anything else would be absolutely OK with me.

She wanted to see our jetted tub. My wife and I have a big jetted tub in our bathroom, and before long, LuLu and I were luxuriating in the warm water. I started to follow her lead. She was rubbing her pussy with one hand while conversing with me. So, I started touching my flagpole of a penis.

We were laying in the tub facing each other. Me at one end, her at the other. Our legs overlapped, her feet coming almost to my crotch. After words of encouragement about how big my penis is (it’s only an average 6 inches), and how nice it looks (it’s just an average penis), she scootched forward a bit, and placed her feet gently against my balls, as I widened my legs as much as I could in the tub to allow her better access. She then started kind of grabbing my penis awkwardly between her feet. Finally, with only her feet, she jerked me off, until I released big jets of semen into the water. As I had one of the strongest orgasms of my life, she cheered. Before we left the tub, as my penis was reducing in size in post-orgasmic glow, right there in front of me, as if it was the natural thing in the whole world, LuLu rubbed herself to a series of strong orgasms.

Shortly after our bath, she went home. My wife welcomed me in bed with lots of kisses (but nothing else), and asked, “Did you like my gift?”

Surprising Kid

Surprising Kid, Sexual Memoir

This boy was a great kid. Raised well. Quiet and polite. Good-looking too. You don’t have to be gay to admire the look of tall, skinny, blond boys of Nordic descent who wear their hair long.

I’ve known his mother for quite a while. In fact, we dated back before he was born.

Now, having just graduated from high school, he didn’t know what he wanted to do. She was secretly relieved he didn’t want to go to college, because after his father left, they were in poverty and she could never help pay for his education. She hatched a plan, which turned out quite well, and all she had to do was one thing. She suggested he ride with me for a week.

I wasn’t at all interested in having a kid tag along, but I did it because it seemed important to her.

Monday morning, I pulled up in front of their shabby little garden apartment and he met me promptly in front with an eager greeting. If he was reluctant to participate in his mother’s experiment, he didn’t show it to me.

It was a half-hour drive to the first appointment. Trying not to offend him, I let him know in no uncertain terms that he was to be as invisible as possible. I figured the last thing my clients would want is to deal with an 18-year-old kid. Other than that, it was mostly small talk on the ride.

We got there and he helped me drag the air conditioner out of the truck, and unboxed it while I set up the lift and removed the old air conditioner from the motorhome. I appreciated the help. Maybe dragging him along wasn’t going to be so bad after all.

I had asked him to be unnoticeable, but what was the first thing he did? He started a conversation with the motorhome owner. The client seemed to like the kid. It kept the client out of my hair while I finished the installation, and so that, too, turned out alright.

We went to the other appointments of the day – trailer brakes, a generator that wouldn’t start, and sealing a roof. Driving between jobs, the kid told me he admired my truck. It is something I’m proud of, and so it was nice to hear him speak about how much he thought it was cool. He went on to call it a ‘Swiss army knife’ of vehicles. It’s true. Although the truck is big, and sometimes annoying to take into narrow driveways or to park in tight places, it carries a lift, welding equipment, and every tool you could possibly need in the RV repair business.

The week wore on. Having the kid around turned out to be good. He was helpful. He would just do grunt work, such as spreading cat litter on an oil leak and sweeping it up, without even being asked. He was intelligent too. For instance, I’d be on a roof, and without me requesting it, he’d climb up the ladder with a 7/16″ wrench, handing it to me right when I needed it.

I have to admit too, I had been kind of lonely rolling around in that old truck by myself. I enjoyed the chatter between jobs.

Until one day, he stopped me dead in my tracks by asking whether I ever masturbate.

We were at a traffic light at the moment he asked. I think I turned red in the face, and was concerned that the people stopped next to us saw me, maybe even heard him ask the question. Geez! How does one answer that?

I must have formed three or four answers in my head before I finally said, “Well, sure, doesn’t everyone?”

Slowly, he wedged masturbation into several conversations during the next week or so. I gradually opened up becoming more used to these conversations, even enjoying them. Secretly, I had jerked off the past several evenings, remember our conversations. He had admitted having phimosis, and seemed to want to know how ‘ordinary’ people jerk off.

I acted like I knew what that was, but didn’t have a clue. I tried to look it up on the internet that evening, but couldn’t remember the word. I tried “flamotis” and all sorts of things, and so didn’t find an answer. I was very, very curious. What could possibly be wrong with the kid’s penis? Or was it something affecting his semen production? Something about his balls maybe?

The next day we had a case where the client wasn’t around. I was replacing the CV joints in a classic old GMC motorhome. I admitted to the kid that I didn’t know what phimosis was.

He said, “Here, look.” With that, he stood up, unbuckled his belt and lowered his pants and underwear. He grabbed his penis pulling it forward and showed me.

My heart leapt into my throat. I would not have expected that reaction. I was suddenly feeling very horny, and from a kid, an 18-year-old boy! Who knew that I had any homosexuality in me at all? Oh, sure, I goofed around with the kids in my neighborhood when growing up once or twice. I remember giving and getting a couple of blowjobs. They were alright. I kind of enjoyed the experiences, if also feeling guilty about them. Mostly, I played with the girls as I was growing up. I knew much more about pussy than dick and by the time I met the girl who became my wife, I was already experienced in the ways to please her. I still miss her. To this day, I’m afraid of small cars.

But I’m getting off topic. There he was showing me his penis. He acted as ordinary as if he was showing me a pocket knife. My heart was unaccountably racing. I didn’t understand what he was trying to show me. I saw a nicely formed uncircumcised penis, with the foreskin totally covering the tip, and coming to a point.

I had seen uncircumcised penises before. Who hasn’t seen some online porn involving an uncircumcised guy? He must have seen my confused look so he came right out and told me: “The foreskin doesn’t pull back.” He demonstrated by pulling his foreskin somewhat. I was starting to understand. So that’s phimosis. The foreskin covers the tip of the dick and can’t be retracted.

His pants were back up in an instant. I didn’t know how to react. I didn’t know what to say. I turned back to the brake rotor which I was putting back in place.

That evening had me jerking off big-time in response to that little scene earlier in the day.

Nothing more was said for the next couple of days about phimosis, although the kid did bring up masturbation a couple more times. So did I. It was mostly him asking silly questions, like “Do you think it’s OK to jerk off more than once per day?”

I would respond, telling him things like ‘In my day, we weren’t very open about sexual matters. I discovered masturbating on my own. I wish times then were like times now. We were all isolated and afraid.”

By now, the kid was on my payroll. He had become officially my apprentice. To my delight, he was loving the work, and never complained even when there was something repetitive or difficult to be done.

He started asking to see my penis. First it was very shrouded, like, “I wish I knew what a normal penis was like.” or “I’ve seen circumcised men online, of course, but have never seen a circumcised dick in person.”

Within a week, it became blatant. “Hey, when are you going to let me see your cock?”

I kept refusing. It just wasn’t right. Was it? I mean, here I was more than three times his age, and I was having strong sexual feelings about him. In a way, I was starting to feel that having invited him to ride with me was a mistake. This sexuality was making me very uncomfortable. At night, I was jerking off resulting in crashing orgasms, with memories of looking so briefly at the kid’s dick in my mind. I was fantasizing about sexual activities with him.

One morning, I asked why he didn’t just get circumcised. He said he had read about adult circumcision. It requires a painful recovery. I offered to give him time off so he could get that done. He winced, saying that he would never, ever let anyone cut on his dick.

I asked whether he’d rather go through life with phimosis. He replied that he’d rather die than get surgery. It’s true, in other conversations, I had discovered that he’s deathly afraid of the medical system. He hadn’t had a physical exam since before he could remember. His fear of doctors was like my fear of small cars.

He said that he didn’t have to go through life with phimosis. He had read about exercises that would eventually stretch his foreskin as long as he was patient.

I was like, “Ok, so do the exercises.”

He replied that he couldn’t.

Now I was confused. “Why not?”

“I’ve tried a few times, but I just won’t pull on the foreskin enough to do the job. I kind of hurts a little bit, so I stop. I need someone to do it for me.”

I’ll bet you know there this conversation is going. He asked me to do it. I refused, knowing secretly that I’d like nothing better than to get my hands on his penis. Over the next few days, he kept bringing it up. Finally, he was practically begging me to do it. I kept pretending that I didn’t want to, because I knew that… Well, what did I know? Was there something wrong with helping a kid in need? Was it gay? Af it it was gay, what was so wrong with that? Would my wife look down on me from heaven with shock, horror? No, I knew her. She’d be amused. Actually, if she were alive today, she’d probably talk me into it. She’d want to watch. Or participate. That’s the kind of girl she was. Very bold and forward and I loved her for it.

He wore me down. One Thursday driving from the first to the second job of the day, we arranged that I’d take him home to my place and do his exercises for him. I was so nervous and jittery the rest of the day I could hardly work. I actually dropped a screw into the panel behind a refrigerator and had to spend time fishing it back out. The kid seemed kind of nervous too. What a long afternoon it was!

Finally, finally, we were in my place. I offered him a beer. He refused, saying he wasn’t going to follow in his deadbeat father’s footsteps. He didn’t even want one sip of anything alcoholic. Good for him! I handed him an orange juice, and got myself a beer. I couldn’t drink it. My throat was tight. My hands were shaking a bit. Weird, eh?

“Well, how are we going to do this?” I asked.

“Um, let’s go in your bedroom.”

We went in. He started pulling off his shirt.

“You don’t have to take off everything. You can just pull your pants down,” I offered. As soon as I said it, I figuratively kicked myself. Of course I’d like to see the kid all naked.

He said, “No, it’s probably better to do this one hundred percent,” and continued removing his shirt. Then his shoes and socks, then his belt his pants, and finally his underwear.

He was erect! The minute his pants were off, his penis bobbed right up at a 45-degree angle. There wasn’t any hair there. The kid was evidently into manscaping. The skin was quite white, especially his small, tight scrotum. His penis was smaller than I would have expected. Not much wider than my thumb.

My heart was racing! I was visibly shaking. I could hardly stand up.

“C’mon, you too!” I was surprised, and delighted. I was always body dysmorphic, thinking I’m not very good looking. But, he wanted me naked. I pretended to balk, but he insisted, and soon, my clothes were entirely off also. I was erect. I too, had been manscaping my genital region. Somehow, I was slightly embarrassed for him to know that.

The boy looked at me, and quietly said, “Beautiful.”

Who knew? Later, I came to realize that this boy was not only mostly homosexual, but totally into older guys. And not just any older guy. He loved me. Right from the first day!

As our relationship grew, I knew there was something I had to do. I was dreading the day. I had to let his mother know what was going on. It’s not like I was a pedophile or anything. The kid was old enough. But still, it was highly unconventional. And old guy and a young kid. And both male, for heaven’s sake!

I invited her to lunch. I sheepishly started trying to bring up the subject of me and her son. Just as I was taking my first crack at opening that conversation, she said, “I know about you and Tony.”

Hearing her say that scared the crap out of me. She said it calmly, but what was going to happen next?

“And I approve,” she quickly added, evidently seeing my agitation.

She went on to explain that this had been part of her master plan, that it went farther than she expected, yet she was delighted.

She knew her son needed a trade. She knew I was in a lucrative business. She figured her son was mechanically inclined. She went on to say that she also suspected, more.

She knew that I had been without what she called ‘company’ for several years. She knew that her son was gay. She knew he seemed attracted to older men. She thought, maybe, if everything worked out just right…

So now, Tony lives with me in my house. We continue to ride together to all our clients. He has continued to grow into the RV repair business, knowing almost as much about the repairs and installations as I do. Oddly, we seldom argue. I think it may be because of the vastly different perspectives, him being so young, and me so old. Then too, his mother raised him well.

As to his mother, she and I have recently been kind of half-dating. She’s almost as bold, outgoing and adventurous as my wife was. She and I haven’t had sex, but we have masturbated each other. What a joy!

Now, I’m not one to do things behind anyone’s back. Before I did anything with his mom, I asked Tony whether it would be OK. Not only was it alright, he was very supportive of the idea. To my shock, he suggested all three of us could have a masturbation session together some day.

When I told her about his idea, she smiled big, and said she’d love that. Fact is, so would I. I’m sure it will happen soon.

So what about the kid’s phimosis? From that first day, we worked on that. He laid down on my bed. I pulled up my rolling chair next to the bed while my heart continued to race. My knees were so weak I had to sit down. I gingerly put my thumbs and fingertips on his foreskin and pulled down slightly.

“Ouch.”

I wouldn’t have expected it would be that sensitive. Phimosis is a real, and bothersome condition. He encouraged me to pull down a little bit again, even though it was mildly painful for him.

He was still totally erect, so I guessed it wasn’t too painful. I, sitting in the chair, was totally erect also. I didn’t do anything about it. After all, this was about Tony, not me. But he was staring at my dick like it was the only thing in the world.

I worked the next several minutes, balancing pulling down on his foreskin to the point where it hurt him, but not too much. Suddenly, he ejaculated, writhing all over my bed.

I was so delighted that I ejaculated a moment later without even being touched. I must say, it was the first hands-free ejaculation of my life (but not the last.) It was a very strong orgasm.

Days turned into weeks. We faithfully did his exercises every morning and evening. For the longest time, the exercises ended with him ejaculating prematurely. He’d then turn his attention to me, jerking me off to a crashing orgasm. Sometimes, after doing me, I come back to him, jerking him off in an ordinary way so he could cum again. He was often good for twice in a row. Sometimes I could do that too, but generally, once was enough for me.

We experimented with other sexual techniques. We kind of liked giving each other blowjobs, but we mutually agreed they didn’t measure up to our lovely – and loving – handjobs.

Our experiments with anal intercourse turned out to be non-experiments. I really like the look of his puckered pink asshole, but it’s small. Maybe because he’s tall and skinny, but there’s no way a guy could get a cock in there. Well, maybe that’s an exaggeration. I’ll bet he could be buttfucked, but he’s not into it, and neither am I. We both very much enjoy me putting a finger in his anus. He’ll finger me too.

For the longest time, there was no way he could buttfuck me, not that I would have wanted that. I’m just a mutual masturbation guy, through and through. The phimosis would have prevented anal intercourse. I don’t know what would have happened if he tried putting it in someone’s vagina, but we never found out. In time, the phimosis did reduce. He can now pop his foreskin back behind his fully erect glans, but then it still takes a minute to get it to pop back into place. It no longer gives him any pain at all, but we’re still doing the exercises. Might as well do it one hundred percent. Doing things ‘one hundred percent’ is one of Tony’s favorite expressions.

As to his mother joining us, all three of us are excited by the idea. However, we haven’t quite made the move to make it happen yet. Maybe we’re afraid of the dynamics it could set off. Personally, I believe we all have great personalities, and our relationships will only improve. I’m sure it will happen soon.

Stripe

The young man came to me, a friend of his father, because he was greatly concerned about what he called a ‘stripe.’ At first he was reluctant to show me, but at the same time, he was bursting to show someone who he could trust, and might be able to put his mind at ease. After a bit of hemming and hawing, I just told him to drop his shorts and I’d take a look.

I had him lay on my bed, and although the situation was slightly embarrassing, I did take a close look. His penis looked normal in every way, and I told him so.

“No, look,” he said, as he grabbed his own dick and turned it so I could get a closer look at the underside. “See, there’s a slightly darker stripe leading down along the bottom from my circumcision scar down to my balls. In fact, if you look closely, you’ll see it continues down my scrotum as well.”

He came to me with a concern about a stripe along his penis

I pushed his fingers away, and took his penis into my own fingers. I noticed it seemed sort of puffy, like not fully flaccid. I did see the stripe he was talking about. It didn’t seem so bad. In fact, I could sort of remember noticing something similar on myself. I told him so.

“Well, I think maybe the doctors went crazy when I was circumcised as a baby,” he said. Then he said, “Or, maybe, I needed some sort of operation that my parents never told me about.”

“Quit obsessing.” I told him. “I’ve got the same thing. I think it’s normal.”

“You’ve got a stripe?”

“I think so. I never really paid that close of attention to it.”

I was still holding his penis, and it was definitely getting a bit bigger.

“Well, can we compare?”

“No.”

“No?”

“Too weird,” I added.

There was something in his expression. I assumed that he was still obsessed that his ‘stripe’ was a problem of some sort. He seemed really, really concerned. You know how you get when something is bothering you, how it keeps playing on your mind. Like the corner of the screen protector on my phone is peeling up. It’s driving me crazy. But this was the kid’s penis. I could see how one could obsess over that big time. So, I relented, hoping that my ‘stripe’ would be visible enough to satisfy him.

So, I pulled down my pants. I let him look close. I let him touch my penis, and turn it this way and that. My, it felt good! But, I must not pay attention to that. Geez, I was starting to feel an erection coming on.

“Yes, I see it,” he sighed with great relief. However, he hadn’t let go of my penis yet, and it was starting to truly swell up. I was becoming mortified. The last thing I wanted to do was get sexual with my friend’s son. What would the kid think?

But it was becoming too late. I was going into a full-blown erection. Trying to deflect the situation, I asked, “Why didn’t you just bring this up with your dad?”

“Are you kidding?”

I understood. His father was a rather conservative sort. One didn’t discuss sexual things with his father.

“Hey, you’re getting hard!” he noted.

“No I’m not!” I hurriedly exclaimed.

“Yes, you are. Go ahead and admit it. It’s OK. I’m not going to tell Dad or anything.”

“Well, I suppose it’s a natural response to being held.” He was still holding my penis. Why, I wondered? But then, why hadn’t I gotten off the bed to end this craziness?

Before I could say anything else, he started stroking his fingers up and down along my penis. I wondered whether it was a sort of natural unconscious reaction. I didn’t stop him. It just felt too nice. In fact, if I recall correctly, I might have said, “Ummm!”

The stroking became much more than something unconscious. The kid started jerking me off in earnest! That orgasmic feeling that everyone knows and loves was starting to build up in me. I stopped him. Not because I didn’t want to cum, but because I wanted it to last. Plus, knowing the nature of men, most men, I figured I’d better return the favor before I ejaculated.

So, wordlessly, I pushed him back down on the bed, leaned over him, and started massaging his penis, which I noted was already fully hard. It didn’t take too long to bring him to the edge, then I stopped.

“Hey!” he practically yelled.

“It’s called edging. Let’s make it last.”

“Um, OK,” and catching my drift right away, he returned to me, and started stroking my penis again with his soft, still boyish fingers. Unfortunately, I’m not the super-hero I’d like to think, and I ejaculated almost immediately.

He smiled while wiping the cum off his fingers.

“That was great!”

“Why, thank you.” I replied sheepishly.

As soon as I recovered, I came back to him, and stroked his beautiful cock. Within a minute, he ejaculated fiercely all over his stomach, chest, and even shot a drip onto his chin.

It took him a minute before he could speak again. The first thing he said was, “Let’s do it again soon.”

I agreed.

Strange Family

I grew up in the craziest family I know, and the funny thing is, for a long time, I thought we were normal.

Well, I knew my moms were unusual from an early age. Most families have a mother and father. My moms are not only lesbian, but they are sisters. Twin sisters.

They decided to adopt children. Four children to be exact, all at the same time, and all the same age. Our moms went to Eastern Europe, toured around a bit, and found the four of us at an orphanage. We were three years old. They filled out the paperwork, and the next thing you know, we’re in America learning English.

We are two boys, and two girls.

Now, let’s get to the sex part. Our moms encouraged us to be sexually expressive from an early age. They said that many good psychological and physical things spring from healthy sexual appetites. They should know. Mom Kate is a dermatologist, and Mom Laurie is a psychiatrist.

Specifically, as soon as we got the birds and the bees speech, we were also encouraged to masturbate as much as we wanted. Maybe even more than we wanted. Beyond that, we were left on our own. Our parents didn’t participate. Evidently the two of them had plenty of sexual activity of their own.

So the four of us got together from time to time and we masturbated. At first it was like masturbation in any family, I assume. We’d talk about the day’s events, friends, school while all sitting or laying around naked in the living room and wanking.

I enjoyed seeing my brothers’ cocks getting hard, and then the stuff squirting out.

As time went on, we found ourselves in a rigid schedule. We’d get together in the living room after dinner on Monday, Wednesday and Friday evenings. It just evolved. No one set out to have a schedule. Well, maybe our moms guided it or suggested a schedule. I don’t know.

We started masturbating each other. The first time I touched the cock of my brother Leo, I was in heaven. If I remember correctly, while I was making him cum that first time, I had an orgasm while touching his cock, not my own pussy. A spontaneous orgasm.

Then another thing evolved. I seem to recall it was our moms who suggested it: We should start practicing various sexual techniques. They told us about all kinds of crazy stuff – our moms have always been open that way. They told us about peegasms, edging, multiple orgasms, anal stimulation, and more.

We each picked something to work on.

In my case, it was inner labia pulling. I get plenty wet when aroused, so it is very difficult to pull my inner labia since they are so slippery. That’s part of what makes it fun. So over and over every time we’d get together, I’d have one of my brothers pull my inner labia as best he could while my sister and other brother would massage my feet and my nipples at the same time. My gosh, I had great orgasms!

Kyle especially liked the that a boy can have orgasms without ejaculating. He really wanted to learn how to have this thing happen where his urethra would contract as if ejaculating just once, but nothing would come out. He wanted to get these single contractions every minute or so. He organized us like the director of a movie. It was impressive how he had everything figured out.

He laid down on a sheet on the carpet in the middle of our living room. I was to jerk him off, but every time he said “wait,” I had to stop for a minute. My sister Jen was to be the monitor. She’d place a finger in his butt to feel for the orgasmic contractions. And Leo was to massage Kyle’s balls.

And that’s what we did that first time. It went off without a hitch. Sort of. When he was approaching orgasm, Kyle said “wait.” I did, but a moment later he started ejaculating all over the place. Jen was delighted to report that she did indeed feel the contractions squeezing his anus rhythmically around her finger.

We did the same thing for weeks, until Kyle became so good at it that he could have a single urethral contraction, and not cum, over and over again. Finally, he’d let go and splash cum all over the place.

My other sister and brother had their own sexual exercises with which we helped them. If there’s sufficient interest, I’ll tell you all about those exercises, and the many other things we did as a family.

To bring this to a close, I should mention that our moms put all four of us through medical school. We all chose our own specialty. All four of us are married in the normal sense, and have kids of our own now. We love our moms, and are thankful for such a spectacular, intelligent and loving upbringing, but we’ve all decided to be somewhat more conventional.

43 First Time Blowjobs

Compiled By Spurtz

1. “I tried my best, but he kinda just wanted to fuck my mouth like they do it in porn. That couldn’t really happen because I had a hard time with my teeth. I wasn’t that good, so I just told him masturbate into my mouth. He came, and I swallowed. I believe the only reason I swallowed because I had Brussels sprouts early that day that I didn’t like. So in the moment, the cum didn’t taste bad. I don’t remember the taste of it though, all I know was that it tasted better than Brussels sprouts.”

2. “Awkward. I had no idea how to keep my teeth from touching it. I was next to a fish tank and I felt so judged by all of the fish.”

3. “We were both 14. We hid in the bushes somewhere. He was rock hard which scared me, and dribbled into my mouth for what felt like forever. He groaned a lot and said my name in a dying-battery type of voice.”

4. “Common sense tells you dicks should taste like skin… because they’re covered in skin. Sweaty skin. But that was still a surprise. I was like licking the inner soft spot of someone’s sweaty arm.”

5. “Oh, my god I’m about to put a dick in my mouth! Am I doing this right? God, I hope this is right. Should I actually SUCK?! Yeah, lick right there, that’s the ‘sensitive’ part… damn this is tiring. My mouth hurts. What do I do when he cums? What if I gag/puke? Does he like this? Oh no. He’s gonna cum, that’s what you wanted, right dummy? Blech it’s warm, slimy, and salty. Mostly slimy. Try to swallow. Nope. Just let it coolly ooze out of your mouth on his dick. That’ll work. He’s found you out! Apologize. Grab towel and wipe off mouth. Cuddle. Fall asleep.”

6. “It was my 22nd birthday and I had gotten in a huge fight with my former best friend, who happened to be at the same bar we were at celebrating my birthday. I was upset so I just poured shots down my throat (ended up with over a $200 bar tab). Was dancing with a guy and got really turned on so I told him I wanted to go down on him. We went out to the patio area where I thought was secluded and pulled down his pants and I started to give him head. I was drunk so I don’t remember anything but him moaning a lot, and then somebody came out onto the patio to stop us. Turns out, we were right in front of a window and everybody saw. I started crying and my friends got me home. Almost four years later and I STILL have not lived this down.”

7. I was 16. I been crushing on a neighbor guy for months. He was your typical teenage bad boy. He asked me to skip school one morning and go over to his place. He’d never given me the time of day before. I go over around 8:30. He’s not wasting any time. He takes me straight to the couch and we start making out. He unzips his pants and kinda pushes my head down. I was aiming to please so I didn’t resist. I’m doing my best not to scratch his dick with my teeth, and he starts pushing on the back of my head. I gagged a little. He did it again, I gagged again. I asked him to please stop pushing on my head because it was making me gag. Turns out this guy was a fucking asshole. He did it again, harder. I puked all over him. Covered his dick, balls, pants, underwear, couch, and floor with my breakfast. He yells ‘What the fuck!?’ We both jump up, he’s disgusted, I’m utterly mortified. He runs to the sink, I’m frantically looking around for a towel or something. He turns to me, puke covered pants around his knees, dick still dripping chunks and tells me to just leave. I ran home crying. Never talked to that fucking asshole again.”

8. “First blowjob I ever gave was hands-down the worst blowjob ever in the history of blowjobs. It was my best friend’s brother. My best friend was super psycho protective over her brothers, so I was terrified she was going to wake up and come beat me up the entire time I had this dick in my mouth. Literally had no idea how to go about the deed, so coupled with my bone-gripping terror, I more or less chewed on his dick until he came. Not sucking, or licking, but gentle gnawing with my panicked eyes glued on the door. I had never seen a dick in real life before, only pictures. He was Native American, so it freaked me the fuck out when his pubes were stick straight instead of curly. There I am, a terrified virgin gnawing away at this alien member until he came and I literally ran out of the room and didn’t talk to him for almost a month. Flash forward years later. Dude tracks me down on Facebook, and starts randomly sending me videos of him jacking off, telling me he’s never gotten the feel of my teeth out of his head, and no blowjob will ever be as good. Fucking weirdo.”

9. “I have never been more aware of my teeth than I was at that moment. I’d had it hyped up in my mind so much that you keep your teeth far, far away from the penis or it will be absolute agony that I was convinced he’d be better off sticking his dick into a spool of barbed wire. Turns out, unless you’re straight-up chomping away at it, it’s pretty easy to keep them out of the way.”

10. “Oh man, I did so much research beforehand ha-ha. I Yahoo’d it, and downloaded porn so I could study up. I practiced shoving my toothbrush down my throat, for deep throat practice. I read that it’s hard on your jaw, so I chewed lots of gum to train my face muscles. I think I took notes and everything. You could probably make a Rocky-type montage of my blow job training as a dorky teenager with acne and braces. When it came to the deed, I was so nervous and I felt like I was taking an exam, and literally switched from technique to technique: mint in mouth, fizzy water, warm tea. Then sucking, swirling the head, blowing on tip, to name just a few. Deep throat, but only once lol. I think I just confused the poor guy’s penis, but he came anyway, because he was also a super inexperienced teenager.”

11. “Terrifying, I had no clue what I was doing. The family computer was in the living room so any Googling was risky. I got my tips from Cosmo. When I started humming my boyfriend asked what the fuck I was doing.”

12. “He was guiding me through everything so that was helpful. ‘Right there… just like that. All the way up and all the way down. Try not to use your teeth. Wanna try using two hands?’ Me: ‘My mouth is getting kinda tired’ Him: ‘You can just spit on it and stroke it for a while with your hands—I’ll warn you when I’m getting close.’ But during it I felt pretty powerful looking into his eyes and hearing him softly moan every now and then — knowing that I was the one causing his pleasure.”

13. “‘Ok… Here we go… I hope I’m not horrible at it. Ok… Hmmm this isn’t too bad, ok, apply some of the things you’ve seen in porn and some advice you’ve gotten from Cosmo. This doesn’t taste like anything… Good! No teeth! No teeth! Ok… Alright, he’s enjoying it… I think… Ok good… he’s moaning, good sign. God… ah! WTH? Oh, he came. Oh ok… Good. Hmmm cum doesn’t really taste like anything. Consistency is kind of gross. Not as bad as I thought. Interesting.’

14. “Pretty awkward. I just kept thinking, WTF am I doing? I feel dumb. Does he like this? Well he for sure did and came all over my shirt as we were about to go to a pool party. I tried so hard to get it off but I was a rookie and used hot water! Now I love doing it. It’s probably my favorite thing to do. I don’t even need reciprocation. 10/10 my boyfriend is a happy man.”

15. “For me, it was an experience of ‘Meh? Meh.’ That’s pretty much how I still feel about it. For him, I guess it was either the best or the worst thing he had experienced. He came while laughing and kept laughing for a good five minutes after while I felt stupid and embarrassed and thought ‘Welp, no porno or Hollywood movie ever told me about this part’.’ I didn’t dare ask him if it was laughably good or laughably bad and to this day, 10 years later, I still have no idea if he and his friends knows me as the terribly bad or terribly good blowjob girl.”

16. “It was awkward at first. I remember feeling half grossed out and half turned on. He kept telling me to think of it like Go-Gurt. I remember my jaw was hurting and so were my knees and the bastard didn’t even give me a courtesy warning when he was going to cum. I swallowed most of it but some of it came out. He said he thought it would be better if he didn’t warn me… even though he knew it was my first time!”

17. “We were watching his favorite movie and I didn’t have the heart to tell him I wanted to make out… so I started getting fidgety and thinking I totally could give a blow job. I could touch the back of my throat and not gag. So I started playing with him, trying to be sly and the conversation was like,

Him: W-what are you doing?

Me: Do you trust me?

Him: Of course I do. (Bright red face)

Me: Then keep watching your movie

And it kinda happened. I had no clue what I was doing really, I mean, I read some articles because I wanted to know do’s and don’ts. But he definitely didn’t expect it… and I didn’t expect him to cum that fast. But I swallowed. It didn’t taste as bad as I thought it would. Just made me really thirsty.

We’re still together today.”

18. “First of all, this was the first time I had seen someone of the opposite sex naked. So this was also this first time I had seen a penis in real life that didn’t belong to some kid whose diaper I was changing. Being 19 this wasn’t only mildly embarrassing, but also strange because we were in my dorm room and the girls that lived next to me were in their room making a bunch of racket. So we get started. Lucky me they were huge, I could already see the outline in their briefs, problem was I have a small mouth. (Being a dork) I had read something off handed on a Cosmo magazine about ‘how to give the best head’ and tried to keep that in mind. Something about using an 8 count?

Underwear comes off and the thing is right in front of my face, But I could hardly get it in my mouth, and when I could it was practically prying my jaws apart. I could only go about 1/5 of the way down, it was insane…

Ended up just licking it really awkwardly, and using my hands mostly. At the end of it he just told me ‘it was okay, I guess.’

19. “It happened for the first time about 7 months ago. I had like no experience doing ANYTHING sexual at all, so I figured a BJ would be the simplest option for me. We were both on the couch and I started off with a HJ. The feeling of it was so foreign, yet so intriguing at the same time. The warmth of his dick, the way it pulsates… as much as I had fun playing with it, I quickly realized that this wasn’t going to mean much in the long run since I really had no idea what I was doing. I couldn’t tell which part of the dick felt better to touch or rub, it looked all the same to me besides the obvious head and shaft parts. The only thing going for me at this point was a few tips I read about on Reddit prior to this. After a few minutes of that, I laid down on my stomach and took his dick into my mouth. It was like playing with a meat-rod joystick that took up most of the space in my mouth. There wasn’t a taste of it that stood out to me, it was more like texture of the dick and the thickness of it. The head seemed very smooth to me, the underneath of the head suddenly more rigid, and the shaft feeling like it was just THICK. I recall running my tongue around his head, wondering how much he was getting from this. I didn’t go very far down on him, I was focusing only on the head and upper shaft.

My mouth is pretty small, so it wasn’t going to take in a lot during this first encounter. The further I shoved it in, the more I felt like I was going to gag. I was pretty good with making sure he didn’t hit my teeth, but I probably still sucked (in a bad way) at it because I went on for 15-20 minutes before he pried me off. Granted his sister had woken up and was walking around the house but that was the end of it for a while. The next day my mouth was sore, my throat hurt (despite not going in that far), and I felt like I was SURE I got some kind of STD. Within a week, it went away but I was scared for a while. I honestly felt like I fucked up the whole experience and he would never try again with me. To my surprise, he still kept on visiting me and tried again with me like after a month or so (when we were finally alone again). I think my third time I finally got him to cum after 10 minutes. I was also going MUCH further down on him (to a point that it hits my tonsils now) and I used way more tongue as I was pulling him into my mouth. When he finally came, I took it all in and swallowed. It was like a sort of mucus to me in both feeling and taste, but I didn’t mind. I felt finally rewarded after failing a few times. I had my hand at the very base of dick and loved the feeling as it shook intensely from his orgasm. I still feel kinda clueless since the two of us don’t communicate well, but given that he’s always so close to me, he seems to be enjoying it. Hell, I’ve caught him making quick glances at his stiffy as he’s sitting next to me on the couch, as if he’s anticipating what I’m going to do next.”

20. “Constantly worrying about sucking too hard/not hard enough/accidental teeth, plus the most awkward situation of my mouth being busy but not my brain. So I’m sitting there with this weird fleshy thing in my mouth like ‘…I can’t see anything but pubes… he’s not doing anything, am I doing this right?… this smells weird.’”

21. “I was almost twenty and he was my first boyfriend. He goes to an extremely conservative Christian college that does not allow women to be in the men’s dorms overnight, so we were sleeping in the backseat of my car in a deserted corner of the parking lot. We’d had sex before, but never oral. As horny as we were that night, we knew from experience that trying to bang in my back seat would be difficult, cramped, exhausting, and likely to get us caught. (The story of how I lost my virginity.) But a blowjob we could get away with. I volunteered, but warned him that I was clueless and would need help. He guided me through it very kindly and helpfully, giving me pointers on how to lick and suck the way he particularly liked it. He has an ex that we was with for a long time and was sexually active with, which normally bothers me a little, but that night it was helpful because he was able to be specific on how to angle his dick into the side of my mouth so I could deep-throat without choking or biting too hard. He said it was fine if it scraped against my molars a little bit. He gave all this advice in a low, gentle voice and stroked my hair. It was actually really nice. Once I’d gotten the hang of it, he started pushing my head down, which messed up my rhythm a little, but I get off on being controlled during sex so it was kind of hot. I still ask him to do that sometimes. When he came, I only knew because he warned me — I didn’t realize that the taste in my mouth was cum until after I swallowed. He didn’t expect that. I gave him a weird look and asked him what the hell else he expected me to do with it. Spit it out on the floor of my car? He reciprocated via fingers (cunnilingus proved a bit too difficult in the car) and we fell asleep cuddled up in the backseat. We’re still together. All in all, a very pleasant first blowjob experience.”

22. “I got nauseous and gagged a lot. He said it was okay if I stopped. Then I started crying because I’d wanted to do something special for his birthday (we’d been dating about two months at that point) and he said it was fine and we’d try some other time.”

Got my period two days later. My period makes me nauseous and weepy. Many a-ha’s were a-ha’d. (I did end up successfully completing a blowjob like two months later. My general reaction was “wow, this is really sour and kind of savory, it’s not salty at all.”)”

23. “Awful… for him. I had braces and I’m still not sure why he would knowingly accept a metal BJ. He soon learned it was not a good idea when a part of the band on my molar met his dick.”

24. It was with my ex-boyfriend 3 years ago. I was a virgin at that time. My ex-boyfriend was 3 years older than me and had a good star boy vibe too.

It was my first time touching a dick. felt so heavy and warm. When I start giving him the hand job, it suddenly got hard like a rock but went soft again. When It got soft a droplet of precum came out of his penis top. I got so horny by witnessing that. I licked it, it was slippery and salty, OMG I loved it. I wanted more precum, so I pulled out all my strength and started sucking out his dick. I felt that salty liquid, Yes he is a precum machine. He got rock hard again, I was on my work, mining out all his precum up to the last drop. Suddenly he started moaning and I felt his dick was getting fat and harder. This dude squirted out all his cum, which I had never tasted in my mouth. It was more like precum but was warm.

25. I was immature to say the least and lied to him when he asked me if I had ever sucked cocks before… it’s the reason I still crave the cock sucking as soon as I put his cock in my mouth I had a climax but at the time had no clue what it was but it happened once more when he squirted his cum in my mouth… I thought he had just peed in my mouth till he said swallow the cum so there would be no mess in his car for his wife to find…. I waited till he dropped me off to get sick and throw up… When he asked me 3 days later to do it again I could not wait and I never have gotten sick since.

26. Tonight was the night for me. My boyfriend and I, we have been together for a year and a half and we celebrated today with a great dinner and a great loving session after.

Although we don’t want to go into sex yet, we have been doing some other things and two months ago it was my first handjob on him.

Tonight tho, I asked him if I could kiss him down there. And he smiled.

I went down kissing his chest and then started to move my boobs on him. He was super excited. When he was almost coming, I put it in my mouth and he held my head with his hands as if he was liking it. No longer than 30 seconds after, he came in my mouth. It was a weird feeling, having a penis in your mouth is weird but I was liking it even though I was confused. When he came, I was amazed and not sure about what to do so I swallowed it. He couldn’t believe it. It was amazing and we both loved it.

27. I was so proud! I had studied books on the subject and watched a few porn videos. Then, I discussed it with my boyfriend. He was so supportive, and let me know that if I were uncomfortable with the idea of putting a penis in my mouth, that he would understand and not expect it.

Finally, I decided that I would try it. In fact, a co-worker who said that she was an expert, always said, “Try it – you’ll like it.” So I told my BF that I wanted to give it a try.

He took me to our favorite restaurant for a delicious meal, and even got us some fine wine – for liquid courage. Later, at his apartment, he again asked if I were still sure that it was something that I wanted. At that time, I wanted nothing more than to get on my knees before him!

The actual act was much better than I expected. He offered suggestions, and waned me that he was about to cum. I had gone this far, so I pulled him closer, and would not let him pull out. I swallowed every drop, and still do!

28. From all my sexual experiences at first I’m always a bit nervous in my head bc I have to think about it and figure out my first move while beginning to suck. When I start I always close my eyes to relax my nerves because it’s always my first time especially doing it with someone new. But after I start feeling like he’s liking it, I get comfortable and begin doing some sexy tricks with my tongue 😅. Sooner or later he’ll tell me he’s about to cum or when he starts breathing harder I tend to get myself prepared for it. As soon as he does it, It’s like my blood rushes through the inside of my skin and the taste of his sperm in my mouth gets all salty and thick with a light chemically taste that fills my mouth like a donut 😩 and it makes me feel good that he climaxed and I’ve made him do that with my wonderful mouth and tongue.

29. The first time I did it I was very nervous and didn’t like it. The second time was on a guy I met at a party. That was a ten-second wonder. After that I found ways to enjoy it. Later I took a class in it! Seriously! Honestly, if my vagina sealed itself up somehow I would specialize in oral sex. It’s something my bisexual husband and I compare notes in and share techniques! LOL!

30. My first was awkward and a bit surreal, I was deeply in love with the guy and I was fairly young and still in high school. I had read about sex and saw everything there was to see from tons of foreign and domestic porn that my best friend and I would watch after she found the secret hiding place her father used to keep it, he had every type of porn known to man and on sleep overs we certainly got our fill in her little hide away in the basement we called our nest. I used to see lots of blowjobs and oral sex on those old video tapes though I was not eager to really try it out. However my boyfriend was begging for it so much that one day I did attempt it with him in his parents garage, it was very awkward and I did not like or even realize there would be scents or odors and taste that were not really appetizing or to my liking at that time of my life, I was so afraid that I was not doing it well but he did instruct me in a pleasant and loving way, it did not take him long and without warning he lost what felt like gallons of his manhood in my mouth, I coughed and gagged and he held my head strongly against his tummy forcing himself into my mouth to where I felt like I would not be able to breathe again, when it was over I threw up on his shoes and his pants and ran to clean up, after a couple more times I began to adore pleasuring him but the first couple times were very rough on me.

31. I was 14 and went to a private Baptist school and it was just me and the preacher’s son in the gym that day and on a bullshit bet he told me if he made a full court shot one handed I had to do whatever he wanted. Well he made it and he wanted me to suck his dick and I did and have enjoyed giving head ever since 30 years later.

32. Odd especially since I was pretty young. I was 10 and was pretty dense and reserved back then. I was with some friends and one of them was 16 (Maybe older). Things escalated and I was dared to suck his dick. Not wanting to be the shy one out I agreed. We went to another room and he showed me his penis. He was pretty big if I remember correctly. I was only able to fit his penis half way. He tasted bitter and salty. To be honest I kinda liked it. The feeling of doing something naughty like that. He then came in my mouth without warning. That tasted even saltier and I kinda didn’t like it but he held my head and his penis in so I swallowed it. He told me to lick him clean so I did. At the time it wasn’t an overly traumatic event but in hindsight was pretty stupid.

33. I was nervous, and the guy was giving me directions while I was on my own. He kept telling me that I was using too many teeth, then I got the hang of it. He was starting to really enjoy it until he decided to shove more stuff in to make me choke. For me it was the most difficult, fortunately with practice I improved a lot.

34. I was nervous but excited to do it. I had practiced on my dildo many times, so I was excited to try it for real and make the boy feel good. I wanted to impress him with my skills. But I was nervous that I wouldn’t do it how he liked. He came pretty quick, so I must have done a good job. Either that or just seeing me do it made him cum fast.

I met my husband when we were 11 years old at school but didn’t start dating till we were 13. We kissed, cuddled and ‘played’ with each other and when we were 14 he went down on me and I returned the favor. I can remember whilst I was giving him a BJ, all I was thinking was “Is this really in my mouth?” I did stop before he came in my mouth and I finished him off by hand. Because I was so scared of getting pregnant we were have foreplay long before ‘full sex’ and it wasn’t long before I let him cum in my mouth.

I was surprised that I actually enjoyed it, more so because we were a couple rather than a one night stand. It give me a sense of bonding with him. Anyway, we’re 34 now and 21 years later I still enjoy pleasuring him and have honed my skills to an absolute art.

35. AWKWARD. I was 14 at the time and I had been rather sexually aware for a couple years. I met up with a guy called “S” who I had been talking to online for 6 months or so (he was 17) and we went to a secluded park where before I knew it we were making out. It was kind of a blur and I couldn’t tell if he liked it or not as I was inexperienced and very nervous. He came which was a plus!

36. My first time I felt scared and confused. I was 16, he was 18. He liked it but when we and by that I mean, he, was done I felt lonely and used. Subsequent experiences did get better but I never felt 100% comfortable with it until 2 years ago when I began having sex the most wonderful man I have ever known. He’s now my fiancé. With him I feel beautiful and sexy and loved no matter what kind of sex we’re having at that moment. It’s so much better! I love sucking his dick and swallowing his cum.

37. I practiced up ahead of time with cucumbers, carrots, and bananas until I figured out how to get something like that in my mouth without triggering natural reflexes to spit it out or gag on it. I got to where I could almost skin the peel off a cucumber before I dared actually try it on him.

That evening, I (we) had started playing around with one another, and I have to admit, I had as much fun playing with his penis, pulling on it, slapping on it, bending it, pinching it, and even biting it before I went for it. He was practically ready to cum before I got it in my mouth good and proper. I was having the time of my life, until he did. That sudden explosion of gook was more than I could handle. My first thought of it was a time when I had been sick and coughing up a thick and pasty phlegm. The thought of that almost made me nauseous.

I still to this day have a problem when he unloads in my mouth. I don’t mind it when he pulls out and splatters it all over my face. Even if he gets a few droplets of it in my mouth, it doesn’t bother me. It’s not the taste of it, it’s the amount and the texture of it. YUK!

38. My first – It was great, but it was very tiring! I had slept over at his house and then we were in bed watching a movie and cuddling. After we both fell asleep, in the middle of the night I woke up a few times and kept holding him, then I gradually went down and felt him up a lot of times. He was sleeping peacefully and he kept getting hard since I was rubbing it. He woke up and asked me if I was trying to feel him up lol and I said “Noooo…” and then we kissed a little, talked, went back to sleep and I went back at it. Then in the morning I woke him up and he was so turned on because of last night and I did it again, he took his pants off because I asked him to and I gave him a hand job, then he asked if I wanted it in my mouth and I put it in and he instructed me how he liked the grip, pressure, etc. He wanted it to last very long, to me it felt like an hour and I think it was. I loved watching him squirm around and go crazy as he was about to cum. I swallowed. We planned that I’d show him the come in my mouth but I just could not keep it in there too long because the taste surprised me. It was a warm, salty tangy taste and I had to swallow immediately and drink water but I enjoyed every minute of it. He loved it because I loved it.

39. Felt awesome. I had no clue what I was doing but made him feel great. I was told that I was the best and wasn’t believed when I said it was my first time. I rocked it.

40. It was awkward, my jaw started hurting, I didn’t know what to do, then he shot this hot, thick, bitter liquid down the back of my throat and I started choking lol!!!! I am a pro at it now though.

42. I was scared to see a penis from that angle for the first time! It was just… so close to my face. But once I started, I loved it instantly.

43. “‘Holy shit, what am I doing?’

‘Whoa, this is awesome!’

‘I love cock!’

‘I’m-a deep-throat this thang!’

‘Oops, I’ve thrown up…’”

Strange Approach to Lesbianism

Piano teacher, strange approach to lesbianism

I’ve been taking piano lessons from Helen forever. Well, actually, ten years, since I was eight years old. I want to be like her someday. Helen earns a nice living at $60/hour teaching kids, and adults.

I already have some students. I love a genre called ‘Roadhouse Boogie,’ but can also play and teach jazz and classical. In fact, I like most types of music. But what I really enjoy is imparting a can-do attitude on my students that comes with learning music. I also like the interaction. One gets to know one’s students, and it’s almost like having a large and wonderful family.

Helen is like a mother to me. She kind of looks like a 30-something version Meg Ryan, with shortish, curly dark blond hair, a thin body, a very thin neck, and rather large boobs.

Me, I’m Hawaiian, through and through, although people who don’t know any better have mistaken me for Korean, Japanese, Sumoan, even Chinese, if you can believe it. I keep my shiny black hair really long. I can almost sit on it.

Even though I’m already a pretty good pianist, I still take lessons from Helen. These days, the lessons are more about business coaching in the world of teaching piano.

I find Helen rather attractive, and I have a feeling she kind of likes me. I mean, to see her eyes sparkle when she looks at me sometimes. Well, I like that. I never thought of myself as lesbian or anything. Yet, dare I admit, I have masturbated with her in my mind at times.

We’ve talked about everything. She knows about my family situation, and I know hers.

So, it wasn’t too much of a personal stretch the other day when I brought up my little problem. For the past couple of months, I’ve been constipated.

She just came out and told me I have to eat less junk food, especially sugary things. She said I have to cultivate an enjoyment of salad. I didn’t really want to hear that, and I’m sure she knew, because she then rocked back on her piano bench the way she does, looked me right in the eye, and then… hesitated.

“OK,” she said, “I don’t know whether I should tell you this…”

“What?”

“Well, uh… I read an account recently about a man who claimed to his girlfriend-to-be that a finger pressed into the anus brings temporary relief from constipation.”

I don’t know why, but I found just hearing that terribly embarrassing. Was I embarrassed for her, having brought up such an intimate thought? Or, was I embarrassed for me for some reason?

The discussion soon turned back to business, and that was that.

However, the thought rattled around in my head for a few days. The idea of Helen sticking a finger in my ass brought instant chills to me, and I had to go in the bathroom and give myself an orgasm more than once.

At our next meeting, Helen asked whether I was eating better, and how my constipation was coming along. I had to admit that I was still hooked on eating cereal in the morning, sandwiches for lunch, and so on. I was still constipated. However, the line of questioning caused shivers in me, and I couldn’t resist asking, “Hey Helen, can you tell me more about the finger in the anus thing?”

“Does that sound like something that might be useful?”

“Actually, maybe… yes, yes I think it might be helpful.”

“Would you like me to help you with that?”

Oh, my god! As soon as she asked, my heart leapt into my throat and started beating a hundred miles an hour. I’m sure I blushed big-time.

“Um…”

I realized I couldn’t even complete a sentence. Couldn’t even work out the thought. I would love to experience such a thing, but dare I admit it?

Realizing I had paused for a long time, I rushed to form a complete sentence. “I suppose it might be worth a try.”

Then editing myself out of some sort of worry that I had said something really bad, and at the same time not wanting to kill a possibility that this could really happen, I added, “I mean, this constipation is really quite annoying, and well, maybe, well, I think it might be… yes… a good thing, I think.”

Unfortunately, Helen had students all day. She invited me to return to her house at six that evening. I can tell you, I was full of springs all day. I could hardly think straight. It just seemed like forever for 6pm to roll along.

Finally, there I was in her living room. She said, “Let’s go through to my bedroom. I think we’ll be more comfortable there.”

Once in her room, after a long and uncomfortable hesitation, Helen said, “OK, let’s just do this. No fanfare is necessary. Why don’t you take off your clothes?”

“All of them?”

“Well, you could just pull down your knickers, but that seems kind of inelegant, don’t you think?”

After some more hesitation and awkward small talk, I found myself fully naked in Helen’s presence. I also found myself shivering, although it was actually warm in her bedroom. Helen, meanwhile, was fully clothed.

I was kind of embarrassed about my small breasts, and the fact that I keep my pussy hairless. I also didn’t want to seem too eager, for some crazy reason. And yet…

“You know…” I began, with my voice actually shaky, “I’d be more comfortable if wasn’t the only naked person here,” and I tried to laugh.

“Ah, I understand. Furthermore I was hoping you’d ask.”

At this point, I knew we were BOTH too far gone to turn back. We had both essentially admitted to each other that we’d like to do what it was obvious that we were going to do.

Helen stripped, and I have to say, that woman has the most beautiful breasts I have ever seen. Very white, full, heavy, hanging down against her chest, with big nipples, Oh my! She turned at one point, and her ass was to die for. I guess I find white people very attractive, or at least Helen sure was.

I found myself face down on Helen’s bed. She had me spread my legs wide so she’d have access to my asshole. Evidently, she had prepared for this, because she had some coconut oil, which she spread on her finger. I felt the gentlest and slightly cold touch against my anus itself. The very center of my being in my opinion. My, did that feel great! If nothing else had happened, I’d have a memory to masturbate to for years to come.

But much more did happen. True to her word, Helen worked her finger deep, really deep, into my rectum, and it felt so good that I was wetting her bed with the juices flowing from my vagina. I orgasmed. I tried, mostly unsuccessfully to suppress a moan.

Helen laughed good-naturedly. “Was that an orgasm?”

“I’m afraid so,” I squeaked out as I was coming down from the sexual high.

“Do you want more?” Helen asked, even though she didn’t wait for an answer. That delicious finger of hers started pushing in and out only about 1/4-inch. I was so sexually high at that point, I couldn’t even speak. I was just like, “Ummmm, ohhhh.”

“I hope this isn’t too intimate,” she said, and with that, she managed to place another finger in my very wet and slippery pussy. Orgasm city!

I had, never in my life had more than one orgasm at a time. This was the first occasion where it was just orgasm after orgasm.

When things finally died down, she withdrew her fingers very slowly. The one in my ass seemed super-long as it kept coming out for what seemed a very long time.

I rolled over on the bed to face Helen. She climbed on top of me, embracing me in the best hug of my life, and then she started kissing me.

Who knew? I mean, up until then, I had the occasional random thoughts of a sexual nature with Helen, but men had been in my sex fantasies also.

As the weeks went by, Helen and I played often. It’s true that eating better cures constipation. Or maybe it was the repeated butt-fingering. I did the same for her, even though she wasn’t constipated. I did much more for her too. She taught me how to really be a woman, with all it’s sexual context.

At first, I worried about this lesbian ‘thing’ quite a bit. I couldn’t even bring myself to say the word ‘lesbian.’ I watched a couple of Netflix movies involving homosexual women, and didn’t really care for them. But in time, I came first to reconcile being lesbian, and then to embrace it. A year later, I was a major LGBT advocate.

I was scared to death when I finally came out to my parents. It was needless. My dad just went, “Hmpf,” the way he does when he learns something that doesn’t particularly interest him. My mother was more verbose saying that both of them knew for quite some time that I’d probably be interested in girls. Evidently, they were totally fine with it.

Just last week on my birthday, Helen had a huge surprise for me. Her brother was at her house. I had met him before. He’s a big, strapping police officer.

With the two of them smiling at me in a certain way, and the way they were carrying on, it was soon obvious to me what they were planning. More than once I had told Helen that I wondered what it would be like fucking a guy. She had tried to give me the effect with a hairbrush handle, and then a soft dildo she bought on Ebay, but I kind of wanted to experience the real thing.

That evening I lost my virginity. On the one hand, I was rather intimidated by his massiveness, his hairy body. On the other hand, I have to say, having your vagina, your body, spread wide and filled with a penis is a super fulfilling feeling. Helen sat there rubbing herself to orgasms as she watched me and her brother getting it on. I love Helen!

Sperm Glue

Children twins and sperm glue

Growing up, I was always the shy one, and my twin sister, who doesn’t look anything like me, by the way, was always the outgoing, loud, but also the protective one.

I know it’s crazy but we seldom argued. We grew up in a loving, and open-minded family.

One day when my parents were downstairs and my sister and I were in her room playing Monopoly, she showed me that a corner of the board was peeling up. She just came right out and asked, “Does sperm make good glue?”

I told her the truth, “I have no idea.”

Even at that age, I knew she meant ‘semen,’ but didn’t bother to correct her.

“Do you want to find out?”

I enthusiastically told her yes.

I didn’t have to take anything off, because it was a hot day, and the air conditioning in our home didn’t keep up, so both of us were starkers.

The Monopoly game was forgotten as she had me recline on her bed, and she reached out to start producing semen from me. My little, hairless penis became erect right away. I had to show her how to stroke me up and down because never having done it before, she was hesitant, and way too gentle, barely touching me at all. It was less than a minute that I felt that wonderful feeling, made even more wonderful because it was her hand on my penis, not mine for a change.

Because I was still so young, only about three drops of clear liquid came out. She carefully collected it, and applied it to the corner of the Monopoly board. I felt weird afterward, so I left her room, with the game unfinished.

The next day we laughingly discovered that semen makes terrible glue.

It wasn’t the last time we played together. Our parents even caught us once. I thought I was going to get killed, but all Mom said was a brief lecture against actual sex, that we couldn’t risk getting my sister pregnant. I totally understood, Mom didn’t directly say so, but that basically meant that oral sex and anal sex were not off limits.

Son’s Phimosis

One day, when my son, Luke, was home from college for a two-month break, he and I were sitting in the dining room having a casual mother-son conversation. He asked whether sex is supposed to be painful. I knew he had been having sexual relations with a young lady, and was fine with it. He’s old enough, he’s responsible, and I trust him to make good decisions. It’s me who doesn’t always make the best decisions.

I almost cried when Luke asked about sex being painful. You see I knew from my son’s earliest times that he may have a problem with phimosis. That’s where the foreskin can’t retract fully. It makes keeping the penis clean difficult, and it can cause pain on intercourse. My husband had to be circumcised as an adolescent due to phimosis.

I felt terrible, because on several occasions when doctors advised me to have Luke circumcised, I just couldn’t do it. Especially after my husband told me that when he was cut, it took many painful weeks to heal. I figured at the age of 20, it would be terribly embarrassing, painful, and inconvenient for Luke. You see, I had just hoped it might go away.

In his adolescence, I tried to recommend stretching exercises, but he wasn’t having it. He didn’t even let me finish the conversation the few times I brought it up.

Now, I knew we had a problem. I talked with Luke earnestly right there at the dining room table. I let him know my thoughts about his whole phimosis problem, even that I felt bad for not having him circumcised. He let me know that he was aware of his condition, and even my feelings about it.

“Mom,” he said, “I’m glad you didn’t let that happen to me. I don’t want it now, either. I’ve read of some exercises…”

I didn’t bother to remind him that I already tried to get him to do those exercises years earlier.

He announced he’d start right away, and went upstairs. Presumably, Luke went to his room to get erect and start stretching the foreskin. I know it’s crazy, being his mother and all, but the thought of him doing that up there made me horny. Of course I didn’t do anything about it.

A week later, I asked, “How are the exercises going?”

“Huh? Oh, I forgot all about it.”

Shit. “OK, why don’t you start now?”

“I guess I should.”

A week later, I asked again, and he sheepishly admitted he still hadn’t started. I was surprised how angry that made me. Here he was not enjoying sex, and not doing anything about it. He didn’t want surgery, but that’s exactly where he was headed. Perhaps it was the anger that provoked me to say, “Luke Albert Whitfield, pull your pants down right now.”

He looked like a deer in the headlights. If I wasn’t still angry, I would have laughed.

Thinking more clearly, I commanded, “Well, not here. Come to my bedroom.”

He’s an obedient son, so he followed me to my bedroom. I locked the door so my daughter couldn’t come in, had him strip and lay face up on our big king bed. He was very reluctant. I can’t say as I blame him. I hadn’t seen his little willie since he was in diapers. I was surprised to see how big and hairy it was now. I guess as a mother, one always imagines their children as little boys and girls.

I pulled my dressing chair alongside the bed, and grabbed that penis of his, examining the tight foreskin.

“That tickles,” he giggled.

“Deal with it.”

I was forming a plan of action. I’d do the exercise for him, since he wasn’t doing them himself. I started pulling the foreskin down, but of course nothing was happening with his penis being soft. I knew what to do, and decided I’d have to remain entirely clinical about this. I couldn’t allow the feelings that were boiling up in my lower belly, and you know where.

I got up, went into my office, and returned with a soft little paint brush. I waved it back and forth over his penis, over the frenulum area, until the bristles was just touching his penis. His penis jumped a little bit each time the brush touched it. I knew the effect. This always works very well with Dan, his father, if I want him erect.

Soon enough, my boy was hard. Not quite as big as Dan, but respectable. Very respectable. Actually, it was kind of hard to compare, with that foreskin covering everything up like it was.

My boy was totally embarrassed, but I told him to forget it. I reminded him that I had diapered him. He was like, “Well, you’ve never seen me like this.”

“Oh, you mean erect? Luke, I hate to tell you, but little boys get erections, too. I’ve seen everything. Don’t you worry.”

I went to work, pulling down on the foreskin, holding it for ten seconds, just like the exercises are supposed to be done, then letting go so it can relax for a minute. A couple times I pulled too hard, and he was like, “Ouch, Mom!” but I knew ‘no pain, no gain.’

After ten repetitions we were done. He couldn’t get back into his clothes and out of there fast enough. He disappeared into his room. I’ll bet he jerked off. I know I wanted to do some serious jilling, but I was already late getting dinner ready for Dan and the kids.

The next day at 4pm, I commanded Luke to come back to my bedroom. He anticipated, and walked across the house naked. His sister saw him, but said nothing. I don’t know whether they had communicated about his ‘treatments’ or not.

It didn’t take as long to get him hard. We did the exercises. He stayed hard, and walked back across the house, again in front of his sister in the living room. Was he showing off his naked body and his erection? I didn’t care to think about it.

Next day, same thing, except his sister wasn’t home. He was hard when he arrived in my room.

“Mom,” he said, “These exercises are kind of fun.”

“Don’t you get any crazy ideas.”

“Oh, no, no way, nothing like that!” he assured me evidently as shocked as I was at the thought.

The exercises continued for a couple of weeks. I was proud of my diligence. Seldom in my life have I stuck with anything. That’s why I’m twenty pounds overweight. Diets last about 3 days with me.

On this occasion, as I was on about the eighth stretch, I felt something weird. A kind of pulsing. I knew almost immediately that my boy was ejaculating in my hands.

He groaned, “Oh, Mom!”

I knew from Dan that men don’t like unfinished business. I mean, they hate ruined orgasms, so I did what came so naturally to me. I stroked him as he was cumming, so he could finish his orgasm properly. I immediately regretted it. Had I gone too far?

Feeling guilty, the next day, I told him he had to finish doing the exercises himself. He was in agreement. In fact, he even admitted he had been doing the exercises twice a day. Once with me, and once by himself. “They feel really, really good,” he admitted.

That was a year ago. Those darn exercises really work! He came to me a few days ago, and proudly showed me how far he’s come along. Of course that required an erection, but he had no problem rubbing himself to hardness in front of his own mother.

Five minutes later, I was in my bedroom masturbating myself like crazy, and having the strongest series of orgasms I’ve had in a very long time.

Small Cock

Short memoir by a person with a small penis

It was my friend Jason who first told me. I mean wanking with him, it was obvious that his cock was bigger than mine, but I hadn’t given it much thought. I just thought he was extraordinarily large. Then later, my second serious girlfriend, Mattie, confirmed it. Until then, I didn’t realize my cock was smaller than anyone else’s. It turns out I masturbate and fuck just like anyone else. I mean, my orgasms are just like your orgasms. I’m sure every bit as strong. Maybe stronger. The only differences are:

1. When I stroke, it’s usually with my thumb and just one finger. Sometimes two fingers.

2. Mattie told me that she couldn’t really feel my cock in her cunt. In order to give her orgasms, I had to either use my tongue, fingers, or rub my cockhead all externally against her clit. But she also told me that most women aren’t satisfied, I mean orgasmically, with ordinary fucking.

So, maybe around age 19, I figured out that I really do have a small cock. Since I’m otherwise well-proportioned, and I’m told I have a ‘winning’ personality, I’ve not had any more trouble than the next guy making and keeping friends.

However, I do have a high libido. I really like sex, and even more, I have to admit, I just love masturbating with friends, either male or female. That, I can’t get enough of. I really wanted more, since opportunities were few and far between. Then my confidence coach told me to ‘just go for it.’

At first, I didn’t really understand, and I felt too shy, and, well, I’m sure you know. You don’t just walk up to people you barely know, and say, “Hey, wanna fool around?”

Well, it turns out, I found a way in. A sort of secret passage that works every time. It’s no secret really, and I’m sure you ordinary-cocked guys can come up with something similar.

With a new potential friend, I’ll steer the conversation to sexual matters. It doesn’t take much. Most people are secretly thinking ‘sex’ all the time. Often, they bring up something risque first. I just guide the conversation a little bit. I’ll admit that I have a small cock. Then, I steer the conversation a bit more until I can say, “Wanna see how small it is?” Or, “Let’s see how it compares to yours.” What guy can resist that?

Of course, once the cocks are out, it’s not much of a journey to mutual wanking.

With the girls, the conversation can go more like, “Have you ever been with a guy who has a small cock?” Or, “If a guy had a small cock, let’s say, would you be satisfied with what he could do with his fingers and tongue?” Or, better yet, “My cock is small, but a lot of cum spurts out. Want to see?” Oddly, they almost always say “Yes.”

Here’s the bit that I particularly am proud of: Almost everyone I’ve been with says they are particularly attracted to my small penis. So, I keep it hairless to enhance the effect. I think I look like a little kid, but hey, if they like it, it’s OK with me!

Small and Skinny

Being small and skinny turns out to be a huge advantage.

In my adolescent yers, I was very concerned. I pretty much knew I’d be small, since both of my parents are short and skinny. I wasn’t concerned about losing fights, or being teased by other boys. I was concerned about not having sexual relationships. You see I’m a horndog. As to people teasing or getting aggressive because they think they can pick on a small guy, my karate skills, which I’ve been studying since I was eight years old, take care of that very nicely. My sensei teaches that one never starts fights, but one can end them, sometimes rather spectacularly. Oh, I never hurt anyone, but humiliating big guys who thought they could humiliate me is fun.

But, I’m getting off-topic. I’ve jerked off imagining all sorts of sexual relationships since before I could remember. Before I could cum. I just enjoyed the feeling of stroking my hard little penis. In fact, I’ve enjoyed just walking around with an erection. I’ve always been an exhibitionist. We weren’t a nude household, but let’s just say I’ve been seen by my brother, sisters, mother and father in an erect state on several occasions.

Sorry, I’m getting off-topic again. So the point is, I figured being small like this, I’d be pretty much excluded from sexuality. Nothing could be farther from the truth.

I can’t tell you how many people have come up to me insinuating that they’d like to play. They want to see if my dick is small like I am. I’ll show them, because I know what comes next. It always does, and it’s both from guys and girls. I don’t care. I’m happy with either sex.

So, my dick and my balls are actually small. To enhance the effect I keep that area hairless. Being Asian, I’m pretty much hairless everywhere else except down by my ankles, anyway.

After they see it, they want to touch it. Oh, I’m so happy with that! Sometimes they want to suck it. Then, many of them want to get all sexual. I’m not into that. They’ll have to be satisfied with what I’m willing to do. If anyone gets crazy, although it’s never happened yet, I know karate!

I suppose all these shared handjobs are a phase. I’ll probably find me a nice wife and have a family someday. I hope my kids grow up to be as lucky as I am.

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