My first boyfriend, Gary, had something that I didn’t realize was so important: Staying power. He could fuck me for an hour if he wanted, then he’d cum only while I was orgasming. It was wonderful. The problem was he became more interested in my sister than me.
We were all too polite and considerate to do anything about it, but we all knew. The two of them never got together in consideration of what he and I had. Except one day, it just came out in a tearful conversation between him and I. I think he was crying more than I was, because he really didn’t want to hurt my feelings.
Strangely, I wasn’t all that hurt. I just missed the sex after he and my sister hooked up. I was happy for her that she was getting what I got.
It wasn’t long before I started dating Lance. He’s my landlord, and a super-sweet guy. I mean my first boyfriend was a very kind and gentle person also, but my landlord was on a whole ‘nother level of kindness. At 29, Kyle was 7 years older than me when we started getting serious. Here’s the thing: Lance is wonderful in all ways, except he was lousy in bed.
Lance is a trip. Somehow, during his high school years, he got it in his mind that he was going to be a real estate mogul. Except jokingly he refers to himself as a ‘slumlord.’ He saved for a down payment and bought his first place, a broken down old duplex a month before he graduated. He says he learned a lot while fixing it up, and by mid-summer, while still living with his parents, he had it rented out to two families.
It didn’t take him long to buy another duplex, then a triplex, then a couple of stand-alone houses, and a couple more duplexes. Right now, he has 34 rental units, some of which are entirely paid off. Lance’s motto is “Good housing for good people.” And he means it. He sets ten percent of his profit aside to cover the rent for any tenants who get into financial trouble so he doesn’t have to kick them out. He goes the extra mile in repainting, repairing, replanting, whatever it takes to keep his places nice. Lance still does most of his own maintenance, even though he could easily hire someone. He like that part. He does have someone helping with property management, but he does some of that too.
But that’s not what you want to hear about. The situation is that he can’t seem to last. I mean, when we get together sexually, he cums almost immediately, rolls over, then wants to go to sleep. Oh, he realizes I still want an orgasm, so he’ll finger me, or lick me until I cum, but it’s not like real sex. I mean, yes, we fuck, but it’s over in a heartbeat and it’s just, well, terrible, to tell you the truth.
Lance showed me one of his saws once, a saber-saw. It goes in and out real fast. I had to laugh, because it totally reminds me of his idea of intercourse.
My idea, what I used to have with Gary, is a super comfy feeling. You girls, those who aren’t virgins, I mean, you know. You like being held close and fulfilled. You like your cunt filled with a loving warm cock, and have it stay that way for a while. It’s like cinnamon rolls in the toaster oven. They’re in there, heating up, and you know eating them is going to be so nice when they’re ready. But it takes a while, right?
Despite the whole sexual problem, I married Lance. I mean, he’s such a sweet guy, who could resist? He’s good on the eyes too, at just over 6 feet tall, with curly hair and a trimmed beard to match.
Our one-year anniversary was coming up, and sweet Lance asked me what I wanted. I told him.
You’ve gotta understand: I’m bold. I ask for what I want. I say what I think. And I believe, I hope, people respect me for that. So I told him I wanted to spend our anniversary evening with him finally learning how to properly fuck me. Furthermore, I told him, there may be a surprise in the evening, but he’d just have to trust me.
He said he was happy to comply. I should point out that his one good sexual kink is that he loves the idea of unconventional relationship activities. It’s always just been a fantasy, but more than once he’s talked about ‘accidental’ sexual situations, three-ways, and bisexuality, so I knew my crazy plan wouldn’t be terrible for him. It might even be a great delight.
The morning of our anniversary, we exchanged small gifts, plus he brought flowers, something he does quite often. My stomach was all flutters for the rest of the day as we went off to work. Him, to visit some tenants and replace a water heater. Me, to my job as a speech therapist. I love that work. To see a child master proper speaking habits is a real joy.
Oops, I’m getting off track again.
Evening came. Lance and I ate a nice dinner. Right on time, at 7pm, the doorbell rang, and as expected Gary was standing there at the door.
Lance was like, “What’s he doing here?”
He had met Gary, and rather liked the guy, but one could tell there was a bit of competitiveness or some sort of spikey energy between them. At least from Lance. I don’t think Gary was at all feeling anything negative toward Lance.
“You’ll see,” was all I could manage to say.
I had been planning this evening for weeks, but I didn’t have it fully orchestrated. Gary was aware of the plan. Lance was not.
I got them into a game of strip blackjack. It took some doing to get Lance involved, but a sideways glance from me and a whispered reminder that he said he’d do whatever I wanted was all it took.
I’m sure by the second or third hand when we were all missing the odd shoe and a sock or two, Lance must have had a general idea. I have to say what a good sport he was to play along, and not balk or complain in any way. But, Lance is like that. He’s always happy to make me happy.
Unfortunately, the game didn’t turn out very even. The guys were losing more clothing than I was. Gary was down to his underwear, and lost the next hand. He pulled off his jockeys to reveal an already erect penis.
I looked over at Lance and saw something I wasn’t quite expecting. It was a look of something like terror mixed with huge disappointment. What was he thinking? I have no idea, but I’m guessing it was something like, “This might be the end of my relationship. She’s going to rejoin Gary.”
It was time for me to explain. Abandoning the game and shucking off the rest of my clothing right in front of my husband and former lover, which by the way, is not easy to do when you have body dysmorphia like I do, I started talking.
Yes, body dysmorphia. Everyone tells me I’m pretty good to look at, but I’m pretty sure my legs are too long, my neck is too skinny, and my boobs hang down. I really like the look of those women who have pronounced tits, but not so big that they flop against their lower chest like mine do.
What I quickly and inexpertly explained to Lance is that Gary and I were going to show him how to fuck properly. Then we’d coach him in doing it. I blurted it out with not a little trepidation. The fact was, I was shaking. Shivering as if it was cold in the room when actually it was rather warm, and I was trying hard to keep my voice from shaking.
Now, how was Lance going to react? It takes a lot to get him angry, but might this do it? Might he storm out of the room, and hate me forever?
I didn’t have long to wait. Lance sat there looking dumbfounded for a moment, but then brightened into a big smile, and simply said, “Really!”
How cool is that? He was on-board with it!
We retired to our bedroom, and pretty soon, Gary and I were rolling all over the bed, kissing and hugging, while Lance just sat in a chair idly watching. I couldn’t help noticing that Lance’s thing was rock hard sticking up out of his lap. He started idly touching the tip of his cock, when Gary kindly said, “No, Lance, wait. We don’t want you cumming too soon.”
Lance let go of his cock right away.
The foreplay was coming to a close and it was about time for Gary to put it in me. Lance interrupted, asking whether he was going to put on a condom. I explained it wouldn’t be necessary, since I had only been with two guys ever in my life, and both of those guys were virgins when we met. You see, Gary was young when I met him and hadn’t been with any women. Lance was too busy building his mini-empire to date anyone. So there was no chance of passing any STDs. Furthermore, it was the safest time of the month for me.
We decided to do it doggie style so Lance could get the best view. I was on all fours on the bed while Gary stuck it in from behind. I should define ‘stuck.’ I mean to say he put it in very slowly and gently. Now, his penis is a bit smaller than Lance’s, but somehow, it’s more fulfilling. Maybe because that’s because it has always been so long-lasting and secure in me.
We fucked quite a while, and finally the time came when I was breathing hard, and kind of having involuntary muscle reactions, and felt that super amazing lower body feeling. I’m sure Gary could read the details of my impending orgasm, so he stepped it up a bit, now pushing so hard in and out of me that I was in danger of having my arms collapse dropping me face-first on the bed. I held out, screaming in orgasm, as Gary grunted, and finished his business at just the right time.
I looked at Lance to see how he was taking it. He was all smiles, and his cock was as erect as I had ever seen it.
Gary was the first to speak. “I have been instructed,” he proclaimed, glancing at me, “to help you overcome premature ejaculation. I think I’ve got some ideas. Lay down, face up, here on the bed.”
Lance did as he was told, still smiling big, with his penis idly waving in the air as he took the position.
“Now, your wife is going to hold and stroke your penis. You are not to cum. If you feel you are getting close, say something. Say ‘Wait,’ and she’ll back off for a little while, then build you up again.”
I sat cross-legged on the bed and started working Lance’s cock. It was quickly obvious he wouldn’t be able to hold out. He was on the verge of orgasming the moment I touched it. I spent more time not touching at all than anyone wanted. It was becoming like a meditation session or something.
Gary interrupted. “I see that you are still too excited. What would happen if I take over for your wife?”
Before Lance could object, Gary was cupping his balls in one hand, and just holding his penis in the other. Whereas Gary identifies as bisexual, Lance doesn’t at all. As you might expect, Lance started losing his erection. It only lasted for a couple of minutes. As Gary did any little thing, like let go of Lance’s balls, or change his grip on his penis, Lance started hardening up agin. Pretty soon, he was hard all the way, and it was becoming obvious he wouldn’t last long before blowing cum.
“I’ve got another idea,” Gary piped up. “Butt-fuck me.”
“What?” Lance practically screamed.
“I want you to butt-fuck me. It should work that if I’m not attractive to you, being a guy and all, you can stick that thing of yours in me, and you might just last a while.”
I can’t tell you how excited and horny I was at that moment. To see what I was pretty sure I was about to see was a dream come true that I didn’t even know I had.
“No,” was Lance’s response.
Acting disappointed, Lance asked, “Why?”
“Because it’s gay.”
“So what? I mean, what’s wrong with that? And is it guy if you’re married, and you’re doing it right here in front of your wife, and you’re doing it strictly as an exercise to make things better with your wife?”
There was a long silence.
Finally, softly, Lance said, “OK.”
His penis was totally small and soft.
Gary started gently massaging Lance’s balls, which I thought was a bit weird, but it did the trick. Lance was rock-hard within a minute.
Gary got on the bed in the same position I had been in, on all fours. Lance, seemingly reluctantly, got behind him, and started pushing the tip of his penis against Gary’s asshole.
My eyes must have been as big as saucers. I was riveted. I was in love with both of these guys for giving me such a show!
He pushed, and Gary grunted. It wasn’t working.
“We need lube,” Gary told me.
I went into the kitchen and came back with some coconut butter. Lance grabbed it, stuck his finger is, rubbed it around, then casually applied it to Gary’s whole anal region as casually as if he were lubricating a bicycle chain. Then he pressed a finger slowly but directly into Gary’s ass. I was surprised that he wasn’t bulking or carrying on. Could it be Lance was enjoying this new experience?
A moment later found him trying again. Gary grunted a couple of times, and the next thing you know, Lance was all the way in. He started going in and out. Fast. Like the fucking saber-saw.
“Woah, Big Boy,” Gary quickly said.
But it was too late. Lance had orgasmed. So had I, just from watching. Well, I guess I hadn’t noticed, but I had been rubbing my clit while watching those two guys.
Whenever Lance and I had sex, such as it was, he was done as soon as he ejaculated. I was expecting nothing different this time. But I was so wrong! Shortly after pulling out of Gary, Lance came over to me, and wordlessly, he hugged pressed me down onto the bed, hugged me, and pressed his still-hard penis into me.
And again with the high-speed saber-saw. I asked him to slow down, which he did. Lo and behold, he went a whole five minutes before cumming in me. This was a new world record.
The evening was a spectacular success. In summary, Gary and Lance had experienced gay anal intercourse for the first time. It was the first time Lance had ever cum twice in a single session, and we figured out the magic: Lance needs to cum twice.
In the months that followed, that became our routine which we loved very much. Lance and I would do some kissing and some foreplay. I still couldn’t blow him unless we were OK with him cumming right away in my mouth. But I could massage his balls, run my fingers over his whole ass, maybe even stick a finger in his ass, and stroke his penis. At least a little bit. I still had to pay attention so he wouldn’t ejaculate too soon. Still, he always did cum too soon anyway. But that’s when the good part started. Right away, before going soft, he’d stick it in me, and we’d fuck like an ordinary couple until we orgasmed. Yes, I said ‘we.’ We didn’t always simultaneously orgasm, and sometimes he was just too spent after cumming once, and sometimes he’d squirt again all too soon, and sometimes I came too soon or too late, but we did have our occasional simultaneous orgasms.
I did some reading and found out some things. My early experience with Lance was more typical than my time with Gary. It seems that with literally the majority of couples, the man orgasms before the women. I also found out that a great many women can’t orgasm from ordinary intercourse. They need finger or tongue stimulation. How weird is that? Or, I guess that’s normal, and I’m weird.
We had no repeat sessions with the three of us, and of course I stayed faithful to Lance. Lance did calm down around Gary and the two of them even went on a two-day camping trip once. I wanted so much to know whether they did anything, but they weren’t volunteering, and I was too polite to ask.
Finally, about a month later, Lance sheepishly told me that Gary had butt-fucked him, and he enjoyed it.
I was so surprised, and shocked, and suddenly horny, that I had to be Lance-fucked right away. In fact, that very evening, I got myself butt-fucked for the first time in my life. Even though Lance was slow and careful, it hurt a bit at first. Soon it turned around, the pain was gone and I wanted all the length and girth than his slightly above-average dick had to offer. Now I know why the gay guys enjoy it so much!