Copyright 2017, Jenelle Watson
I’ll admit I’m quite wealthy. It started with my great-grandfather on my mother’s side, who was a grocer during the great depression. It turns out that the food business did well while everyone else suffered. People have to eat, so he had plenty of customers. He invested his money in buying houses around the neighborhood. Then he bought more buildings. You can imagine that his children and their children, and finally my generation have followed his footsteps and all done very well in real estate. So, here I am, a typical trust fund baby with my own house, three cars, an enclosed swimming pool, and all the clothes and toys you could imagine.
I inherited money, but not looks. I have long, frizzy, unmanageable dark hair, a funny-looking hooked nose, overly large boobs, and I’m rather short. Oh, and I’m well-rounded, a bit too well-rounded, if you know what I mean.
On my 18th birthday, I was given a small shopping mall. A 35-store building with full occupancy. Really! I didn’t pay much attention to it. I have managers, lawyers and accountants to take care of all that.
I was also given something else on my 18th birthday. A butler. He used to work directly for my mother, but my parents have been doing a lot of traveling, and don’t want to take him along. They don’t have much use for a butler in the house they seldom live in.
At least that’s what my mom said. I think my parents’ real plan was to have a spy in my house, since I was living here by myself. I’ll bet they figured the butler would let them know if I did anything crazy, maybe he would even prevent me from making any stupid moves. I was actually alright with that.
I knew him well, or at least I thought I did. Edward is a sort of combination chauffeur, personal assistant and dresser. Edward is fairly tall, thin, has slightly graying temples, is very well groomed, and dresses conservatively and well, just like butlers tend to do. If you’ve seen any old Sidney Poitier movies, you may have an idea what Edward is like.
Edward has now been with me for several years and it has worked out very well.
He arranges my air travel, handles my email, and even selects my clothing in the morning. That way, I can spend more time on business. I mean, I could retire right now, and just live off my assets. But somehow, my family has got me so trained to stay focused on growing ‘the business’ as they call it, that I can’t imagine doing anything else. The business has a huge philanthropic arm and that’s what I enjoy managing. Well, I did go to college and received an MBA last year, but that was just part of focusing on the business.
Anyway, back to my 18th birthday. That evening, Edward came in and said he had something he wanted to tell me. I figured he was going to give me a card and box of chocolates or something from the family. Like I needed one more present. I was thinking, ‘I’ll be polite and graciously accept whatever boring birthday gift he has for me.’ Or maybe, he was going to tell me exactly what duties he’ll perform, and which he will not. I could imagine him telling me I had to change the cat’s litter box myself, for instance.
But it wasn’t like that. Not at all. Instead, Edward told me he used to perform a certain very personal service for my mother. He didn’t quite explain it at first. I was starting to imagine the worst. Like even though my mother is a very morally correct and kind woman, I was thinking, “What kind of service? Eviction agent? Supplier of drugs? Hit man?”
He slowly, and somewhat embarrassingly, explained the service. He said that for a while before my mother was married, she was so involved in business that she didn’t have time for dating. Plus, most of the men who came into her life were gold diggers. She got tired of guys who got close to her, and then they had the next great invention which just needed funding, or they absolutely knew that investing in a sports team would be profitable.
I was starting to get freaked out as Edward went on to explain:
He said he gave my mother massages.
Ah, OK, I was relieved. That’s quite reasonable. She may have been feeling lonely in a world full of men trying to hit on her for her money, and found that nice, innocent massages were an acceptable alternative. The human body does crave touch, after all.
I mean, like everyone, I like touching. Fortunately, my religious upbringing wasn’t so restrictive that I couldn’t touch myself even ‘down there’ from time to time.
One time, I did confess to the priest about masturbating. I actually used that word, “masturbating.” It was hard to do – that confession, but I felt in the eyes of God, it was necessary.
I was expecting the worst, but you know what the priest said?
“Oh, my child! That’s not a sin any longer.”
I was like, “What? What do you mean ‘not any longer?'”
“The church used to frown on masturbation, but we must all come into the modern world. It has been proven that masturbation calms the mind and is even good for the body. I myself do it. You can go peacefully, dear child, knowing that you have not sinned in the eyes of the God.”
Like everyone, I had heard that some priests have molested children, so with that statement, I was a bit concerned. Our priest, father Francisco, was one of the good guys, so I decided to take his little masturbation lecture as just what it was – good advice.
Edward went on to explain that my mom continued to receive occasional massages after she was married. And he used to massage my dad from time to time, also. It was hard to imagine my straight-laced dad getting a massage.
So here’s the deal. Edward told me in no uncertain terms that if I’d like a massage, that is part of the service he offers. (And all for $130,000/year. I should give him a raise).
For the first couple of weeks after I turned 18, I did not take him up on his offer. I had never been massaged, and didn’t think I was missing out on anything. Then one evening, after flirting unsuccessfully with a nice-looking guy who didn’t know who I was, and seemed to be attracted to me for me, not my money, I was all horned up. I came home wishing I had hit it off a little better with that guy, and was feeling a bit horny. Thinking I’d just masturbate, I suddenly remembered Edward’s offer, and thought maybe a massage first, then I’d masturbate later in my bedroom. That would be nice.
I found Edward in the kitchen with the cook, just talking about the news of the neighborhood or whatever. For some reason, it seemed inappropriate to ask him for a massage in front of her, so asked him whether he could find my iPad, which I knew perfectly well was in the parlor.
A few minutes later, he found me in the music room noodling around on the piano. I picked that room because it was private. There, taking the iPad he had found, I asked Edward if he would be willing to give me a massage.
“Of course, Little Miss.” That was the name he had been calling me since I was three years old. Sometimes I didn’t care for it, but more and more, I came to feel it was a nice endearment.
“Would you like me draw you a bath, and give you a massage afterward?”
“I’ll set up the massage table in your bedroom.”
A few minutes later found me in the Jacuzzi. Now, you have to understand, it has always been strictly appropriate with Edward. He had never seen me naked or anything like that, although when he has helped me with clothing and such things, he has seen me dressed in a towel or underwear many times. That’s fine, of course.
After my bath, I wrapped up in a large white towel, and rang for Edward in my bedroom. He entered, wearing his usual sports jacket, creased pants, button up shirt and necktie. He’s the classic butler. The only way he could improve on that impression would be to have an English accent, rather than his very slight southern accent.
He had me lay face down on the table, still wearing the towel. He covered me with a sheet, and let me know that I should remove the towel under the sheet. While I was wiggling out of the towel, being careful to stay under the sheet, he had removed his jacket, rolled up his sleeves, put on an apron, and was rubbing some oil on his hands.
I felt his touch on my shoulders first, and it was surprisingly delicious. I wouldn’t have thought it would feel so nice, but his hands were warm and soft, yet his massage of my shoulders and the sides of my neck was firm. I was immediately thinking ‘I’m going to like this.’
He worked on my shoulders and neck for quite a while, before moving down to my upper arms, then my lower arms, and then oddly, he worked on my hands. I had a strange reaction to that. When he started rubbing the palms of my hands, I felt a rather strong twinge deep in my vaginal area. I dismissed it as some sort of normal physiological reaction.
He took a couple of steps to the foot of the table, while instructing me to scoot down. He then started working on my feet. They were hanging off the edge. His attention felt warm and lovely. After a couple of minutes, he pulled on each toe of my left foot, then repeated the pulling on my right. Very nice! After that, I can’t be quite sure because I wasn’t looking, but what I think he was doing was pressing his index finger in the webs between each toe. All I know is that no one had ever done that, and it was excellent. He then resumed massaging my feet in his warm hands, then my ankles, then my calves, and thighs. From there, he moved to my back, where he worked under the sheet with long, wonderful strokes for quite a while. I noticed with satisfaction, he didn’t do anything to my butt, because of course, that would be too, well… private.
I was so calmed down in a way I hadn’t been for a long time, that when he asked me whether I’d like to roll over, I didn’t hear him at first. He asked again, and so I rolled over, making sure the sheet was still covering me.
He pretty much repeated his work on my extremities, with the exception that he also spent quite a bit of time on my face, another exquisite experience.
His voice drifted back into my consciousness. “Would you like more?”
“Your mother often wanted some, ahem, special treatment.”
I couldn’t imagine what he meant by that. Actually, I did imagine something, but surely he wasn’t talking about anything like that.
“What’s ‘special treatment,’ Edward?”
“I’m,.. It’s… I mean… Well, why don’t you roll over on your stomach, I’ll begin gently and slowly, and then you can decide whether you’d like to have me stop or continue.
Hmmm. On my stomach, so certainly it wasn’t the crazy thing I was thinking. Maybe it was “Swedish” massage or something, whatever Swedish massage is. Or “Rolfing.” I’ve heard that’s an intense massage. Maybe that’s why he said he’d start gentle and whether I might not want it to continue.
So again being careful not to reveal anything, I rolled over under the sheet, scooted up, and put my face back in that funny donut-shaped padded thing at the head of the table.
There was a delay as Edward did something with his hands. I think he put on some more oil. Then, I felt him reaching under the sheet and started in on my back again. ‘Very nice. I could get used to this!’ I was thinking. I was also starting to remember how lucky I am. Being wealthy has its advantages. I was starting to wonder if I might want a massage from Edward every evening. That would be nice.
He rubbed my back, focusing on my lower back for a moment. Again, twinges in my vagina. No big deal. It was all so nice. I started to realize that he was doing my really lower back, actually the top of my butt. No one has ever touched me there, and it was nice. Now, he was working on my butt proper. Perhaps I should have been embarrassed, or something, but it was feeling awfully nice. The vagina thing was stronger now. I was feeling sort of like little electric shocks not only in my vagina, but in my lower belly, as well.
Edward switched to my upper thighs, which he had entirely skipped earlier. I noticed he was kind of spreading them out at times. If the sheet hadn’t been over me, he would be seeing my privates. But of course the sheet was over me.
“Is that OK, Little Miss?”
It was starting to feel kind of naughty, but what the heck, it was very, very nice. “Yes, Edward, it’s wonderful.”
I felt a bit of a cool breeze on my upper thighs as he lifted the sheet to where it was just covering my butt, but not my legs. When I was a bit younger, I used to get a kick out of letting him see me around the pool, wearing a skimpy bikini, so this didn’t particularly bother me. Somehow, I was liking the idea that this 50-something, handsome, well-mannered friend of the family was seeing the top of my naked legs. He continued massaging the area. It didn’t occur to me until later that he may have been seeing more than I intended at that point.
The massage continued past my upper thighs to my butt itself again. Then he stopped the way he was doing it with both hands, and did something strange, but something I very much enjoyed. It felt like he took the index finger of one hand, and started very lightly running it along the top of my ass crack. Pardon the direct language, but that’s what he seemed to be doing. I couldn’t tell exactly, since I couldn’t see him. I thought about stopping him, but the tingling in my lower body, and my vagina in particular, had taken over control of my mind. I knew we had crossed a line. I knew I could stop him with a single word, but I really, really didn’t want to.
After a minute of that ass crack stroking, he seemed to just wiggle his fingers for a moment in that gap where my legs meet my ass, and then he backed away.
“We can be done now, Little Miss.” The way he said that let me know that more was available if I was willing. In thinking back on it, he had teased me big-time! How could I not want more at this point, right?
“You went to all this trouble to set up the massage table. No sense wasting your effort. Might as well continue,” I couldn’t believe I said that, because I’m pretty sure I had an idea where this might be going. Or, actually, I probably had no idea at all. All I knew is that he had massaged me, with the most sensuous treatment I’d ever had in my life, and that my vagina was begging for attention. I was certain I’d rub myself to a great orgasm later. Oh, and I knew that he had done a little something to my ass, which I just loved.
A moment earlier, I had been basking in a certain kind of delight that he had been actually seeing my upper legs, and that must have prompted me in my next action. As I rolled over, I normally would have made sure the sheet was covering me properly. In fact, I would have flipped the raised section above my upper legs back down. But I didn’t. And, as I scooted down, and rolled over on the table, the sheet didn’t fully cover me for a moment, and I was OK with that. Maybe even proud in some sort of skewed way. It was only for a second, though. I pulled the sheet back over as I settled.
Edward continued. Again, he worked on my face, neck and shoulders, but only for a minute or two. Resuming on my shoulders, more like the front of my shoulders, his hands worked lower and lower under the sheet until he was definitely massaging the top of my breasts. Intellectually, I knew it was wrong. But I was enjoying it so much, the body ruled over the mind, which I have to say, is unusual for me. Somehow, the sheet slipped lower and lower, and soon it was pretty obvious Edward could see my breasts with their pink, now-erect little nipples and all. Not only did I not object, I was rather proud of what I had there. I might weigh a few too many pounds, but my breasts are correspondingly large, and I’m glad.
Evidently Edward liked what he saw, because he quietly, almost in a whisper, and as if to himself, said “Beautiful.”
Of course massaging the top of my breasts led to massaging the whole things. Then, he did a funny thing. With just his index fingers, he started rubbing across my nipples very lightly. It tickled, but at the same time was something much more, a very strong sensation, almost a craving, that seemed to directly connect my vagina to my nipples. I could also feel that my nipples had become quite hard.
I pulled the sheet the rest of the way off. It seemed like the right thing to do.
Taking his sweet time, Edward eventually switched his attention to my stomach. That didn’t do much for me, but I had a pretty good idea what was coming.
I was right. It started with the lightest brushing of the hairs over my vagina. You don’t mind if I call it ‘pussy,’ do you? I like that word better. He didn’t even touch me, just the hairs. What a feeling! I had no idea.
In time, he pressed a bit further into my little nest of hair, and it only felt even better. I could feel my wetness flowing, and soon enough he was redistributing it the length of my slit with his fingers, brushing between my inner labia, and over my clit.
I felt like I was shivering, but in a good way. I wasn’t cold. I think Edward had raised the temperature in my bedroom. But I was definitely shivering. It must have been from sexual delight. That never happened to me before. I was also on the verge of orgasm, but Edward was an expert, because at just the right moment, or wrong moment, depending on how you look at it, he stopped.
Instead, he started pressing a fingertip just a little way into my opening. Oh my, did that ever feel good! I so wanted him to put his finger all the way in, and maybe even two fingers. But he didn’t, and it was driving me crazy. Then, he slowly slipped his fingertip out, but kept it in contact with the bottom of my pussy, ever so slowly sliding down to my anus. The minute he touched the middle of my asshole itself, I exploded with the biggest, most amazing, shuddering orgasm of my life.
The next few minutes found my with my head pressed against his shoulder, his arms wrapped around me, and I was sobbing big tears.
I think Edward knew, although I couldn’t have put it in words, that they were not tears of guilt, sadness, loss, or anything like that. They were just tears of release. My whole life I had been waiting for something like that, I just hadn’t known it.
And, here I had been thinking that to experience such perfect ecstasy, one would have to have sex. You know what I mean, ‘real’ sex, intercourse.
Without saying a word about what had just happened, as if it was just part of his routine, Edward helped me get to bed, and I immediately fell into a deep, satisfying sleep.
The next morning I thanked him before he drove me to school. I did, however, have a little trouble making eye contact with him. Go figure!
Well, that was a while ago now. Let me tell you what has happened in the meantime.
It certainly wasn’t the only massage I recieved from Edward. In fact, it became a routine. Every evening he’d ask if I wanted him to draw me a bath, which was our little code for bath, massage, and orgasm. About every third evening, I’d be in the mood, and recieved another delightful treatment.
In short order, we both figured out that I am particularly delighted when he puts a finger in my ass during the ‘treatment.’ Just that can sometimes cause a huge, back-arching orgasm. When that doesn’t work, he’ll put two fingers inside my vagina, curl them upward and massage what I came to know as my G-spot, and that does the trick every time.
I had been planning on going away to college, but at the last minute, decided the local university would be just fine. A major part of that decision was that I could stay near Edward and his services.
I’m not one to treat my employees like employees. In fact, that’s a family thing. None of us have treated the people who work for us as if they are only ’employees.’ Everyone gets a big Christmas bonus, everyone gets as much autonomy in their jobs as makes sense, and everyone is respected. So, I offered to reciprocate.
That’s not the only reason I wanted to reciprocate. I started having odd feelings for Edward. Now, he’s around 50 years old, and I was nineteen at the time, but for some reason, I started fantasizing about giving him a blowjob. It got to where I really, really wanted to do that.
So I offered, and he, sensibly, declined. He said he’d have to give me $130,000 a year if I was going to do that, and he laughed.
Over the course of months, as he continued to ‘do’ me every few days, I kept offering, and he kept declining. My offers started getting embarrassing. I was sort of begging.
On my twentieth birthday, he knocked on my bedroom door while I was doing a homework assignment on my computer. He wished me happy birthday. He was carrying a box, and a big smile. I opened the package to discover a pair of vintage Keds sneakers I had admired in an antique store when he went shopping with me as a bodyguard. I could have bought them at the time, but didn’t. Later, I was kind of kicking myself for not getting them. They were way cool.
There was something else. He wanted to know if he could come in and shut the door. It was Edward, so of course. Once in, he started unbuckling his pants. It happened so quickly, I didn’t even notice something strange was happening at first. Then it dawned on me. Here was this beautiful man, the guy I had been wanting to suck for a long time, and my great massaging butler, taking off his pants. That is so far from normal, words fail me, yet at first, I didn’t realize it was happening.
When I saw his super white underpants against his black skin, that woke me up. Yes, this was unusual indeed. It was the first time I had ever seen Edward not fully and properly dressed.
Next, his underpants came down and off, as he stepped out of them. I didn’t see anything at first because the bottom of his shirt covered his crotch area. That situation didn’t last long, as he then took his shirt off too.
He must have been thinking about this for a while, and it must have been as important to him as to me, because his penis was already erect. It was the first erect penis I had ever seen in person. Oh, I’ve seen them on the Internet. Everybody has. Heck, you can look up penis on Wikipedia, and right there, you’ll see them.
As I wasn’t fully aware of at the time, they aren’t usually like Edward’s. His was a rather spectacular specimen. Oh, I don’t think it was much larger than average, but it was super-black, as was his scrotum, too. They were blacker than the rest of him, and he is quite dark. He had a patch of curly hair that was so black it shined in the glow of my desk lamp. The strange thing, however, was that he was not circumcised. He had foreskin that covered the tip of his erect penis and came to a point at the tip.
He caught me staring, probably with my tongue hanging out of my mouth like a thirsty dog. For my benefit, he put the fingers and thumb of both hands on the sides of his penis, and pulled back that foreskin of his, revealing a shiny, big, blackish-purplish knob with a little slit at the end.
Oh, I so wanted to touch that. Or better yet, put it in my mouth. I was believing that was what he was offering. I started to reach forward, but he teased me. “Little Miss, we have to take care of your massage, first. I wasn’t so sure that’s what I wanted at the moment.
Nevertheless, stark naked, as if that was his usual uniform, he brought in and assembled the massage table, and covered it with a sheet. He took his time, which was driving me crazy. All I could think about was that penis of his in my mouth. By the way, during the whole process, it stayed at a nice, solid 45-degree angle to his body, waving from side to side as he moved around the room. Oh, if I could just reach out and touch it, maybe bring it to my face…
But no, he insisted on massaging me. As had become our custom, I unceremoniously slipped out of my warm-ups and T-shirt, laying face down and fully naked on the table. The covering sheet had long ago become a ridiculous unnecessary formality.
As he was massaging my back and my butt, I had an opportunity to reach out and grab that wonderful wiener of his. I though he might back away, teasing me further, but no, he simply said “Ummm!” and continued with my massage.
After doing my legs, he returned to my butt, and placed a finger slowly but directly into my asshole. I almost orgasmed on the spot. He then had me turn over, and he finished my massage, complete with a G-spot orgasm.
After I settled down, he approached the massage table, standing with his penis close to my face. I reached out and grabbed it again. Instinctively, I pulled the foreskin up and down a few times. I was amazed to discover that his penis was hard and soft at the same time. Hard inside, but very soft on the outside. It was surprisingly warm, too.
I couldn’t resist, bringing my lips to that wonderful thing of his, and kissed the skin-covered tip lightly. It, he, smelled nice, like he always does, with just a trace of cologne, but it seemed a bit stronger now. I intended to just kiss the tip of his penis, but almost immediately, I had the whole thing in my mouth, and although the taste was almost unnoticeable, it was very nice.
At one point, he said, “Ouch,”
I discovered I had to keep my teeth away from his skin. I hadn’t understood that.
Instinctively, Edward started shifting back and forth an inch or two. I had his penis in my mouth quite a ways, and the pushing thing caused me to almost gag. I decided to go with the flow, and in a moment, the gagging sensation was replaced with a weird sense of accomplishment, as I realized I was giving my butler a full-on blowjob. I had read about such things, and had intended to only do it mouth deep, not throat-deep, but here I was doing it one hundred percent, and loving it. This was even better than what I had imagined it would be all those months.
Edward started tensing all his muscles, and quietly said, “I’m going to cum.”
I didn’t need a warning. I was delighted that I might get to swallow his cum. However, I did back off a little bit, so I could taste it in my mouth rather than having it shoot down my throat. Pretty good for someone who had never done this before, right? I tasted salty, but I liked it. I was all set to keep going, but he gently pulled out of my mouth, and said, again quietly, as is his style, “Thank you Little Miss, that was amazing!”
Life went on. I continue in my studies, getting massages from Edward every few days, and occasionally, very occasionally, blowing him. I also learned to do testicle massages and handjobs, which he liked very much. But, he seemed to want to maintain a certain employee-employer distance, so would not accept attention from me as much as I might have liked.
I was becoming interested in getting fucked by him, but he made it very clear that was not going to happen. He was single at the time, so I didn’t know what the big deal was. Later, I came to realize he considered it improper for him to be the one who took my virginity. He wanted to be sure it was at the right time, by the right person.
He let something slip one that that knocked my socks off. I mean, it really shocked me. He wanted to talk about this fucking notion of mine. Again he said that he didn’t feel it was right. He told me that whereas he had performed similar services for my mother, he had never had actual intercourse with her.
That rocked me back, because it was my mother he was talking about. I mean, he rubbed the pussy of my very own, super-conservative, who-would-have-guessed mother, just like he had done to me. He gave her orgasms! That creeped me out, and horned me up at the same time. Weird, eh?
But that wasn’t the half of it. He also mentioned that he had done my father, too, and sometimes, both of them together. Talk about creepy. I asked for details, but he said something about butlers don’t talk about their clients, as if he hadn’t just told me about my mother. Had he given my father orgasms too, then? I’d really like to know. I’m super-curious about that. However, I’ll probably never get to find out, if Edward won’t tell me, because, like how could I ask my dad? That would just be way too embarrassing for the both of us.
I started dating a guy who Edward decided wasn’t the right person. He was right, the guy was way too interested in drinking, but at the time I thought that was so sophisticated. To my utter frustration at the time, Edward essentially ran him off.
I started dating another guy who Edward fell in love with. Oh, I don’t mean literally. This guy, Andrew, was not a drinker, and didn’t seem to have any bad attributes at all. He was also quite a charmer. He was tall, polite, funny, and dare I say, very good-looking. He was studying software design, and came from a well-off family, so he wasn’t after my money.
When Drew and I started getting really close, I talked with Edward about it, wanting to know if he had any advice about how to proceed sexually. He seemed to stammer a bit, and ended up telling me to use protection. Beyond that, I was on my own, but he wished me good luck.
One night, Drew bought me a fancy dinner, which I know cost him a good chunk of his hard-earned money. Afterward, in his dorm, which his roommate had magically vacated for the night, we kissed and kissed.
Coming too for a moment, I found his hands wandering up under my sweater and shirt. I aided him by removing my outer coverings and unhooking my bra, silently letting him know that he was welcome to explore. We fell back on the bed, as my bra came entirely off, and he started sucking on one of my nipples. It was as if he magically knew what I would enjoy. He was pushed against my body, and I could feel something in the vicinity of his pocket softly but insistently pressing at the fabric of his pants. His penis was trapped in there at an angle, and it wanted out – badly!
So, the logical thing to do would be to untrap his penis, right? That’s exactly what I did, and discovered it was a marvel to behold. And behold it I did! He was circumcised, and quite white. His balls and whole crotch area was whiter than the rest of his body. He must have been outdoors a lot, but never naked. I’m sure it’s common enough, but I’d never seen the two-tone effect before. Then it came to my attention that I was seeing a lot of skin there. Andrew had shaved for me. His whole crotch area was as smooth as a baby’s bottom. His delicious ass, too, was beautiful.
Having learned a thing or two from Edward, before Andrew could do anything more with me, I leaned forward and put that beautiful cock in my mouth, to his absolute delight. I had him lay fully down on my bed, but at an angle, so his legs were dangling over the side. With one hand, while I was blowing him, I started to poke at his asshole with one finger. I took my finger back, put it in my mouth to coat it with saliva, and the pressed it against his anus again. I pressed lightly and twisted, and soon, most of my finger was in his anus. In the meantime, I had replaced my mouth with my hand, and was just slightly stroking his penis up and down.
Unfortunately, at that moment, Drew came. He ejaculated all over my hand and his stomach, groaning unintelligibly.
As soon as he had recovered enough to speak again, he apologized for cumming too soon. He had wanted to ‘do it right,’ to proper sex with me. Well, I wanted that too. Very much, in fact. But sometimes things don’t work out the way you expect.
The good news is that Drew and I got together again a couple of days later. This time, we were in my bedroom, as Edward knocked elsewhere around the house. At first, Drew was like, “With Edward here in the house, really?”
I decided I’d better not tell him about the activities that Edward and I had been doing, because that might freak him out in some way, but I did tell him “Edward’s cool!” I think he had a little trouble getting used to the idea of having someone in the house while we were going to ‘do it’ but to his credit, he quickly got over it.
We started again, ending up naked, kissing like crazy, and rolling together around on my big bed, which was so much nicer than the little twin bed in his dorm. Somehow, in the midst of that, without really noticing, his condom-covered penis was against my lower body, and moments later, as if totally naturally, he was inside my pussy.
I had thought it was going to hurt. They say it hurts virgins, but it didn’t hurt me. I guess my hymen had been broken long ago by masturbation. Or, maybe it was broken by Edward’s gentle G-spot stimulation. In any case, Having Andrew’s dick inside me was the most fulfilling thing that had ever happened. It felt so nice, so natural! It felt big, too. His penis was long. So long that when he thrusted all the way in, I could feel it bumping against my cervix, but I liked it. I liked it very much!
It was Andrew’s first time, too, and he had trouble staying hard after a few minutes. That first time, neither of us climaxed while we were fucking. That was to come later. On that evening, we gave each other handjobs, which if you don’t regularly do with your guy, well, you’re really missing out. Having a guy finger you, and you rubbing his penis, is a very special and enjoyable kind of sex.
Time passed, and Andrew evolved into my life. He moved into my home and became my family along with Edward. He and Edward hit it off very nicely. Edward tried really hard to be Andrew’s butler too, but Andrew was sort of embarrassed or something, always telling Edward to focus his attention on me. After a while, he did start letting Edward do more and more for him, which I enjoyed seeing. At the same time, Andrew is the kind of guy who had to do things for Edward, too. They even went fishing a couple of times.
One day, Andrew’s mom, Jeanie, came to town. What a delightful lady. I had been nervous about meeting her, but she put me at ease right away. She’s remarkably good looking for her age. She’s tall with long blond hair, and well put together. She also met Edward, and I could swear I saw something pass between them, sort of like sparks. Good sparks, like a love-at-first-sight kind of thing. Chances are, I was imagining it.
I let Jeanie know she could stay in one of my spare rooms for a few days, rather than Motel 6. She was hesitant, but I insisted. I’m glad I did. Two days later, I saw Edward and Jeanie in the kitchen one morning, the cook wasn’t around, and I could tell right away that something was up. They were joking around, and making breakfast together still dressed in bathrobes. Edward in a bathrobe in the kitchen. Unheard of! He was always immaculately dressed by the time he arrived.
I asked where the cook was, and Edward announced that he gave her the morning off, that he and Jeanie were making breakfast. I had to ask, so I did:
“Hey, you two, what’s up?”
They both smiled coyly, each waiting for the other to answer. The pause went on ridiculously long.
Finally, Edward said, “I’d like it very much if Jeanie could stay here a while longer.”
I was delighted for them!
That was two years ago. A few rather strange things happened since. One is what developed between Edward and Andrew. It’s something I didn’t see coming, something that freaked me out for a few days, and then I settled into very nicely. Something, in fact, that I am happy happened, and that it is continuing to happen sometimes.
It seems that Edward gave Andrew a massage, just like he does for me. Yes, I mean complete with orgasm. Andrew loved it! Insisting that Edward is not his employee, he then gave Edward a blowjob. How did I know that? Drew is a very honest fellow, who really believes in communication. He always say it is important to talk about everything. Drew just came right out and told me, not only in front of Edward, but Jeanie too.
When she heard them say that, she laughed her head off. It was contagious. In retrospect I don’t know what was so funny about it, but all four of us found it increasingly funny, and we went from chuckles to out of control hysterical laughing.
That little incident was like a door opening to a magic kingdom. The next thing I knew, all four of us became the happiest family in the world. We also got very sexual. It wasn’t long before Edward was giving his special massages to everyone regularly, but with the others often gathered round. It became no big deal for me to walk, generally naked, into the den, living room, game room, or elsewhere, and find Edward with a big erection in Drew or Jeanie’s mouth, or Drew getting a handjob from Jeanie, or all three of them playing. That is, when I wasn’t part of the orgy myself, which was most of the time. At various times, I found myself enjoying things I would never have imagined, such as sticking my tongue deep into Jeanie’s pussy, or being butt-fucked by Edward. Yes, Edward became as much a part of the family as anyone could, and so any limits he may have imagined in the past have long since evaporated.
Last year, Jeanie and Edward decided to get married. Drew and I said, “What the heck?” and made it a double-wedding.
Well, that’s enough rambling from me for now. Have fun, and I hope all your families can become as successful as mine has been.