Finding My Mission in Life

Last night, I realized I would be a great cuckolder. Another day, they may have been called something different—a rake, a wit, or a Don Juan. But whatever you call it, I have become aware of the fact that I would be good at it. Tell me what you want me to do to your wife/girlfriend, and I'll come back to you with a report of the activities. Let me show you what I mean.

If I'm going to tell you about last night, I should start by telling you a little bit about the people involved in last night. First, there's me. I'm 33, average height, blonde hair, a bit on the skinny side. I'm told I've got a nice ass, and know how to use my fairly normal-sized penis in ways that women enjoy. Then we've got my wife, Maggie. She's about my age, also with a slender build and a beautiful face. She has curly dark blonde hair, A-cup boobs, and an ass to squeeze, but not really to twerk with.

We married about 11 years ago, with almost no sexual history—together or with other partners. At the time, we were just excited to have sex with a real person, and not just our hands. Several years later, I finally came to the conclusion that there has to be better sex than what we were having, or people wouldn't rave about it so much. So I set out to discover what else the world of sex had to offer. And that is how I met my friend Jenny.

She is a few years older than me, way more experienced in bed, and gives the best blowjob I've ever had. It is difficult to not look at her D-cups when I'm talking to her, especially after I've seen them, and her strawberry blonde hair accents her smile. Ours is more than just a sexual relationship, though; we have become good friends as well. Which is why, as I am on vacation with my extended family, I am texting her regularly.

I finally hit my limit yesterday with my tee-totaling, overbearing parents, and decided it was time for a drink. Knowing I would get an earful from my dad for bringing liquor in the beach house where we are staying, I managed to continuously spike my soda throughout the evening of conversation and cards. But, there is something about alcohol that makes me want to share the joys of intoxication with someone else. So I turned to Jenny.

She was at home alone as well, and drinking as well. Swapping drunk texts, the evening flew by, and I think I managed to avoid detection the entire night. As the evening wore on, the conversation between Jenny and I became increasingly risqué, even as I was trying to appear engaged in the discussion of how to handle my two precocious young nephews.

"We should see about playing out one of your fantasies soon," she texted me, just as things were wrapping up for the evening.

I savored the thought as I brushed my teeth, and took my shorts off before crawling into bed. Maggie was already tucked in, watching something on her Kindle. I pretended to read a book, while stopping periodically to look something up, and more often to text back to Jenny.

"I would love that. For now, I'd just take you here, my face deep in your pussy. Until you cum all over me." I replied.

I thought for a moment, then added, "How bad am I that my legs are entwined with Maggie's right now? Does that turn you on more?"

And they were. Maggie had one leg thrown over mine, her ass pressed gently up against my hip. It was more of a tender, "I like being close to you" gesture than it was an indication she was interested in more than sleeping.

"You should grind on her ass. Reach over and gently pinch her nipples" Jenny told me. She wasn't usually one to give orders (she preferred leaving that to me), but we just went with the idea.

"If I do this, we'll probably end up fucking, and I won't get to talk to you any more," was my reply. "Are you ready to call it a night?"

"Put the phone down and fuck her."

"yes, ma'am."

"I want you to play with her nipples, and fuck her from behind. Laying side by side."

"Any other instructions?" I asked.

"report back in the morning. Now go."

So I did.

While Maggie and I are the only ones upstairs, sound does seem to travel well in the house, and we really have to work on being quiet. Everyone else was already asleep, but my two nephews are especially light sleepers.

When I put the phone down, I went back to reading for a minute, but rested one hand on her boob, and started playing with it-rubbing around it, squeezing it, pinching her nipple. She slid over a bit more, and turned her hip away from me so she could push her ass up against me more. I started moving my hand around a bit more, rubbing her thighs, her waist (especially across the front, right at the panty line below her belly button-she really likes that), and over her pussy. I finally stopped and just let my hand rest on her pussy, with enough pressure to feel good, but not forcing anything.

"Are you trying to start something?" Maggie asked me.

"Why yes. As a matter of fact I am," I replied. "I want to do it with you." (Because she would be so incredibly embarrassed if I said, "yeah, let's fuck.")

We set our respective activities (reading, watching her movie) aside and started kissing. My hand still on her pussy, as she began moving her hips to grind against my hand more. At the same time, she reached over and began playing with my cock-light touches on the shaft, cupping the balls, etc. After a minute or so of this, she was hot, dripping wet and ready (and I was already hard from thinking about a) fucking Jenny, b) fucking Maggie and telling Jenny about it, and c) imagining how hot it would be for Jenny to be in the room watching us). She took her pants and panties off, and I took my underwear off. We were in such a hurry we left our shirts on.

She was still partially on her back, partially on her side-the better to kiss me that way. I pushed her over more on her side, and spooned up against her, with my cock between her legs. She quickly got the idea of what I was trying to do (it's a position we had never tried before) and guided me inside her.

There is always something amazing about that first thrust when I get inside a woman. Like the first bite of an incredible meal, or when a shot of bourbon first hits you, you knew it was going to be good, but you are reminded of just how incredible it actually is. I entered her and started thrusting, though somewhat slowly to a) make sure I don't pop out, b) test to see how she is enjoying it and adjust if needed, and c) to keep from wiggling the headboard too much, lest it hit the wall and wake my nephews. She was breathing and gasping like it felt good, but kept trying to roll over to kiss me more. I would kiss her a bit, then roll her back over so we were more sideways, rather than her almost lying on top of me.

I realized that I also had good access to her clit and started to rub it while I continued to thrust. We both liked the combined movement, in part because it sort of gave me the chance to play with my cock a bit too. I used my other hand to play with her tits, gently pinching the nipples, run my fingers in circles around them, etc. as she continued to gasp and grind against me. I loved the view of her hip and ass pressed up against me, knowing my cock was deep in her pussy and that the view of it was blocked by her ass. I don't know why, but even now the idea makes me hard.

And then I came. Long and hard, I wanted to make noise, but all I could do was moan and bit my lip. I pressed as deeply into her as I could, feeling the base of her pelvis dig into me as I shot my load into her.

She continued to move, even after I finished, wanting to come as well. Her movement was more about small adjustments to get my cock to hit just the right spot inside her, while I continued to rub her clit. The position was awkward, and for about three minutes, my thighs, ass, and abs were all tensed, trying to hold the right position for her. Finally I couldn't take the cramps any longer, and had to pull out of her. But, this put my hand in a better position to finger her just right, and she came in less than a minute. Sighs and gasps and catches of her breath escaped her lips as tensed in orgasmic pleasure.

"I love it when you start things" she said as we lay there, her ass still pressed against me. "It really gets me going." And with that, she grabbed two Kleenex to keep my jizz from dripping on the carpet while she trotted down the hall to the bathroom.

While she was gone, I texted Jenny again.

"Mission accomplished. Details in the morning."

"2 fast. Do it again."

I was totally game, but Maggie is a one time a day sort of person. At best, we could try again in the morning, but she was too tired to go again.

"Kids these days. You should at least lick her pussy" was the response from Jenny when I told her we were done. But I didn't see it until I woke up this morning to the sound of my 3-year old nephew running in to tell us it was time to go to the beach.

All I've been able to think about today is how much I want to be told how fuck someone—Maggie, Jenny, the woman on the beach blanket to my left—and reporting back when its over. Its my mission, my purpose, and I cannot wait for the next opportunity to fulfill it.