Most *memorable* sexual experience

AND has a nice story there!... I think we guys should learn something from that.

 

warpedsoaper: MAN! You have need for one more man to join?? I'd do about anything to join THAT orgy!... Ohh

 

my most memorable sexual encounter......................
I was 16 and the guy (sean) was 18. Well It started on a monday I went over to sean's house and we watched donnie darko and we started to kiss and kissing turned into makin out and he swooped me up and carried me up the stairs to his room and laid me onto the bed and asked me ifit was ok if he licked my pussy i told him no. so he stopped and we totally changed the subject from sex to watching pink floyd's the wall. tuesday after school he came over to my house and again with the kissing and all and he asked me if i could give him head and I told him no again and then he asked if he could finger me and i told him yes and it was so amazing i orgasmed spuratically. On wensday he and i cut classes to go to his house and we went right to his room and the first thing i did was push him onto his bed and sat on his face he just went to town and i literally could not get him to stop he told me my pussy tasted so good it's the sweetest pussy he has ever had. finally i told him that i had gymnastic practice and that i would be late. thursday after school i went to his house and all we did was cuddle and kiss. Friday I picked him up and we started to drive to down town and walk state street but we didnt make it out of town. he started to go dwon on me, I guess my skirt was too tempting for him. well i pulled over into the business park and he and ihad sex for hours and hoursall he wanted was to please me and make me feel good. it lasted for atleast 7 hours of having sex or oral.

 

The time I was with two guys.

I was 16, hanging out with two friends and eating a big bowl of jell-o and vodka. I got way too drunk and the three of us ended up in bed together. I wish I had been more coherent because what I do remember was incredible.

 

Well, many years ago I had a girlfriend that was my second sex freak. She could do things sexually that no other woman in my life ever did. She was also a hot mess, so the relationship wasn't destined to last very long. Truth be told, my only interest in her was for sex.

We were in the apartment we were sharing at the time one Sunday afternoon. We started fooling around somewhere in the bedroom I think. After a period of foreplay we transitioned to the carpeted floor. So we're naked and she's on top of me. So, she turns around away from me into the reverse cowgirl position. Once she is situated, she reached behind her and grabbed my cock and slid it into her asshole. I don't think she stopped for lube. Then she starts pumping my cock like a piston. She is going up and down essentially doing squats on my cock. I lift my head up and I'm treated to the sight of my cock going deep into her assole. I have an unobstructed view. It was mind blowing. I'm not sure how long I managed to hold out but I soon exploded and filled her with my cum.

Anal sex was routine for her, but that one time event surpassed anything else that she did anally.

I don't think I've had another woman do reverse cowgirl into her c***, never mind her asshole.

 

The first time I ever masturbated with someone. There's nothing crazy about it. It's just that it was my #2 sexual fantasy since I'd started masturbating when I was 14. But I never heard anyone talk about doing it. And none of the first few girls I dated in college ever brought it up. So I'd developed the impression it was a really kinky thing to do. Also, my desire to do it was so nagging it felt kinky to me.

When I was 21, I started dating the woman who'd turn out to be my first serious relationship. Up until her, I'd only had about a handful of brief flings with girls in college that lasted anywhere from a week or two to just barely more than a month. Most of them were relegated to heavy make out sessions, fingering, dry humping and going down on each. There was one unsuccessful attempt at losing my virginity where I came as soon as I'd put the tip in. So, this woman was really my first true sexual relationship. And when this story unfolded, we'd only had one hookup where she humped my dick to orgasm.

The next time we got together, she came over to my house to spend the night. We were having drinks and started to feel horny. I suggested we run a bath, get naked and finish our drinks hanging out in the tub. When we got out of the bath and were toweling off, I'd never been so boldly and casually naked with anyone before. All my previous hookups were in bed at night with the lights off. Standing completely nude facing each other in the strong bathroom lighting, I got so fucking horny. And the alcohol had me pretty uninhibited as well.

Somewhat unconsciously, and without saying a word, my hand moved down to my penis and I started going at it 100% staring at her naked 19-year-old body. But I wasn't so far gone that I didn't know what I was doing. I kept thinking how I must look from her perspective, hunched forward, beating off while silently ogling her crotch and boobs. Thinking it was all the more worse because I had this idea masturbating in front of someone was as kinky as wanting to pee on each other. I tried to tell myself to stop and that I was being so fucking creepy. But I couldn't. I was on auto-pilot. After a few seconds, but what felt like it had been minutes, and to my utter surprise, she let her towel drape off her body and started staring right back at me from the opposite side of the room, putting her index finger inside the crease of her outer labia and rubbing it around in little circles, not saying a word, same as me.

I couldn't believe it. We did it like that for maybe about a minute before I went over to her and led her to my bedroom where she lied down with me leaning over her as we both got ourselves off. Looking in each others eyes and watching the other person's hand do what they usually do in secret. That was when I was absolutely certain I had grossly overestimated the kinkiness of mutual masturbation. She'd only had sex with one other guy shortly before we got together. But everything about her body language, moans and facial expression told me this was not the first time she'd done this. And if someone who was barely anymore experienced than me had done it before, I knew it must be a perfectly common part of foreplay.

Of course I've masturbated with all my girlfriends ever since. And there were too many times to count that something about the woman or the location or the circumstance made it arguably more thrilling when considered on its own merits. But because this was my first time, the instant relief of realizing there was nothing creepy about it at all, combined with the relief of finally satisfying one of my longest running sexual desires was a gratification that can never be reproduced.

 

In fact, of the 3 or 4 sexual experiences I'd put in a multiple-tie for most memorable, only one is because the sex was that thrilling and kinky and heated and felt like we were both totally in-synch with each other. All the others are only novel because they were the first of something that otherwise would be completely unmemorable. I've had fucking killer sex with pretty much every woman I've slept with for the past 10 years at least. I've done some wild fuckin' things and not all of them were my idea. But when sex is memorable because it's so thoroughly satisfying or wild, you don't usually feel that until it's over, because what makes that kind of sex so intense is that you and the other person let yourselves get completely swept up in the moment. You're both on a kind of auto-pilot. Everything you do takes its cue from what the other person just did. And lays the tracks for what they'll do next. And that's some real shit. Don't get me wrong. However, the times I have sex and can feel it's something important as it's happening are often because it's the culmination of some kind of unrealized potential. I feel so overwhelmed with emotion because all I can think is "Holy fuck. Am I actually doing this?" I don't know if I can put hot intense satisfying sex ahead of that in a list of "most memorable."

 

The gf and I were free for a Saturday afternoon. We had a little smoke and beer at my apartment. She came out in a black teddy and a smile. We started to engage foreplay to oral then to 69. We were both keyed up for bonding . I guess we hit it right, the window was open and it was a cool day. She was so hot in her black teddy and dark hair laying down we went to all of our postions doggy, behind laying down, to her on top . She was getting into it as we went, more vocal, moaning , and using her body back on to me.
We finally got to the missionary and she jacked her legs back . I found the stroke and rhythm. It was like a sewing machine at work. I was making effort sounds also when we heard footsteps coming up the stairway to the neighbor apartment
It didn't matter to us as we were fucking in a frenzy. Whoever it was stopped outside our window. I guess they heard us in action and was quite intrigued by our sounds. I finally shot my wad, and we both laid exhausted. The bystanders went on to the apartment next door .
Later on the gf commented that was undoubtedly the best fuck she ever had.
I remember it well after 45 years.

 

So many
One evening years ago my gf/ fb came over, after a hug and a kiss we sat on the couch and we both did what we asked of each other. More on that soon.
We started watching tv and in seconds her hand reached through the fly of my pj pants, I had no underwear as she asked. She got me hard super fast doing that. I reciprocated and reached under her top, no bra just as I asked before she came over.
Well, soon I was denied access to her breasts when she asked me to stand in front of her, she pulled my pants down and I stepped out of them, she put her hands on my ass and pulled me close so she could give me oral. Soon after she commented I was very leaky, I could actually tell I was.

Then as she kept going I started moaning and she stopped when she felt the throbbing.
Her eyes were big, her face had HORNY all over it, she took my hand and hurriedly pulled me to the room so we could have comfortable sex.

I started on top, it didn’t last long before she asked me to get off. And switched positions.
She rode me slowly to a handful of orgasms doing more grinding than sliding.
After that she gyrated and slid on my cock until I came deep, she continued to another orgasm for herself before she got off me, and I started giving her more orgasms with my hands and mouth.
I did it long enough to get life back in my cock before sliding inside her again, this time I stayed on top until I came again.

 

Most memorable sexual experience? That's easy. It was watching my best friend (who was also my wife's best friend) spend an entire afternoon fucking and cumming in her for the first time. She was terribly nervous about having another guy fuck her while I watched (even though I arranged it), but she loved it, nevertheless. That was the first of countless times and I encouraged him to fuck her just as often as the opportunity presented itself. As for my wife, she went from not being very interested in sex to literally unable to get enough of it. (We had another close friend who really had the hots for her and I'd planned for him to start fucking her constantly as well, but it never worked out.)

I can tell folks how I arranged for my friend and wife to start fucking each other, if anyone is interested.

 

Would love hearing about it and what she thought about you wanting her to be with another man.
For us it was her girlfriends who encouraged her to be with another man.

 

My wife (who I'm going to call "Lisa") and I got married in July of 1979, after being engaged for almost exactly two years. She lost her virginity to me on the night that I proposed to her. (While I was the first man to fuck her, her boy friend in high school did pretty much everything else to her, including petting her head-to-foot, sucking her breasts, finger fucking her, and so on. He desperately wanted to fuck her, but she kept turning him down, citing pregnancy concerns.) By the time I started fucking her regularly, she was on oral birth control, so that was no longer an issue.

For the two years of our engagement, and the first six years of our marriage, her interest in sex was lukewarm, at best. I wanted to fuck her constantly, but had to badger her just to get want I considered a minimum acceptable frequency. If was frustrating for both of us.

Now, I've always been a voyeur by nature. I constantly fantasized about watch another man (or men, if I was lucky) fuck her and cum in her, to her substantial enjoyment. Then it occurred to me that maybe added another man to the mix might kick her sex drive up a few notches. I wanted it to be someone safe, and I immediately settled on Steve, a very close male friend who we constantly spent time with. I knew that he and Lisa were physically attracted to one another, so it seemed obvious to me that I should work to escalate their relationship to something intensely sexual.

I knew that I had to get Lisa on board with the idea first, as I certain that Steve would immediately agree when asked. So, one day I casually mentioned, that it was a shame Lisa had never had the occasion to experience other men sexually before we met, especially since she knew that I’d been with other women before her. I was just interested to see how she reacted to the topic and, initially, she was simply indifferent. Over the next few weeks, I delicately kept bringing the subject up in various ways. Each time, I’d hint a bit more that maybe it wasn’t too late, even though she was married. After all, lots of married couples have confident extramarital sex and I thought it wouldn't be a problem for us. Eventually, after she was comfortable with me broaching the subject regularly, I came out and said that I think she should have the chance to know another man intimately, and that it seemed to me that Steve was the obvious SAFE choice. While Lori didn’t latch onto the recommendation, she didn’t reject it out-of-hand either. I was encouraged. Her standard response to my suggestion of her and Steve “having sex” eventually became, "I suppose… if he's interested", which ultimately evolved into “Sure… if he’s interested.” My thought was always how could he not be? Lori was drop-dead gorgeous and had a body that just screamed FUCK ME! Anyway, now I knew that she was, at least, willing.

After that, I inserted the subject of Steve fucking her into every conversation, just as often as I thought I could get away with it. I wanted the idea to become something that she was so used to that it would seem completely reasonable to her, that Steve fucking her regularly was as acceptable and sensible, at least in theory, as me doing the same. She got comfortable enough with the idea that SHE would occasionally be the one to bring up the subject! Once she became that relaxed with the idea, I knew that it was time to move on to Steve.

I was right that involving him was going to be a brief, straight forward process. It took me a single get-together with him, that lasted less than an hour, to go from having no idea of my plan to agreeing to become Lisa's second sex partner (assuming, he said, that she was willing.) Once that was done, Lisa knew that Steve was going to fuck her, and Steve knew that he was going to fuck her, but neither of them knew that the other knew about the pending relationship change.

Now, it was mid-April and we were having a very warm spring. The three of us used to go out together and sunbathe on a remote beach, on a stream about twenty minutes from our house. Initially, we all dressed modestly, swim trunks for Steve and I, a bikini for Lisa. That was the norm. One day, however, we decided to go to a different spot, on a different river, just over an hour from home. When we got there, there was another young couple already there sunbathing. Further, the woman was sunbathing topless and she was very attractive! She didn't seem the slightest bit disturbed with have two strange men study her bare breasts. Just to be polite, however, we moved to the opposite end of the beach and spread out our towels. Then, to the surprise of Steve and I, Lisa asked us if we thought she should take off her bikini top! Both of us guys said, "Why not?" Without any hesitation, she removed her top, giving Steve his first complete view of her gorgeous bare breasts.

After that, she always sunbathed without a top. A couple weeks later, the three of us decided jointly to just dispense with bathing suits completely and sunbathe nude. We'd usually stay out for several hours, so sun screen was always in order. I made a point of having Steve and Lisa lube up each others backs (since they couldn't reach them very well on their own.) This only lasted for a couple trips before they were both greasing up each others fronts. It started with Steve coating Lisa's breasts (of course, he took way more time than he needed to complete the job.) Before long, he was doing the insides of her thighs and, to my surprise and gratification, Lisa was greasing his cock and balls! As you can imagine, he always sprouted a raging erection, so the net effect was her giving him a very thorough handjob. (She always stopped before he came, but I don't think that was deliberate.)

We were into early June by now, and Steve and Lisa applying sun screen to each other everywhere was standard practice. (I even noticed that Steve was covertly slipping his fingers inside Lisa's pussy each time he sun screened her.) When that day's session of sunbathing ended, I drove us all back home, but once there, I had Steve come inside rather than climbing into his own car and leaving. Once we all got something cold to drink and settled down in the living room. I deliberately picked our one big easy chair, which forced Steve and Lisa to sit next to one another on the sofa. Then, without any preamble, I stood up and got undress. I could tell that this puzzled both Steve and Lisa, but they just looked at each other and then emulated me. I noticed that, when sat back down, they were much closer to one another, almost touching in fact.

I got each of them, in turn, to describe what I'd gotten each of them to agree to, with regard to having sex together. Steve was matter-of-fact about it. Lisa was nervous, but did the same once Steve had divulged his side of things. At that point, they actually reached for one another! I stopped them and said wait until the next trip to the beach. After all, it was only a couple days away.

Saturday, June 15th, 1985 was the big day. The three of us went out to the beach, spread our towels, and stripped. Steve and Lisa started sun screening each other, but that quickly devolved until unfettered petting. Soon, she was massaging his balls and he was finger-fucking her. This went on for about half an hour. Then, they both looked over at me, like they were waiting for permission. I didn't say anything, I just nodded. Lisa immediately spread her legs for Steve, he moved over in between them and guided his cock into her. He started stroking instantly. Lisa wrapped her arms around him and made sure he stayed inside her.

Steve fucked her for about fifteen minutes, during which time Lisa had a couple decent orgasms. Steve eventually came inside her. Lisa held him as deep in her as she could while he pumped and pumped. (That was the day we found out what an incredible cummer Steve was. The volume of cum he produced had to be seen to be believed!) Lisa didn't let him go until long after he'd stopped pulsing inside her. He eventually pulled out, still sustaining a partial erection.

Steve and Lisa cuddled while the three of us talked. My primary concern was did Lisa have a good time, did she enjoy herself? Her reply was a resounding "YES!" Then she asked me if I was interested. I told her of course I was! Steve moved out of the way so I could mount her. I fucked her for a good ten minutes before adding my cum to Steve's.

By the time I'd finished cumming in Lisa, Steve was hard again and Lisa was more than ready for him to fuck her another time. He did so and produced another load of cum inside her that seemed to be as big as the first one. When he was done, Lisa reached for me again. I was shocked and gratified. I couldn't remember the last time that she'd invited me to fuck her, never mind multiple times!

By the time we packed up to leave the beach, Steve and I had each cum in Lisa three times apiece. After I drove us home, Lisa urged Steve to come inside the house and fuck her a fourth time!

From that day forward, Steve and Lisa fucked, at a minimum, three to four times a week. Frequently, it was more often. In fact, it was not at all uncommon for him to come over on a Saturday morning and fuck her six or more times, before leaving in the evening. On those day, when he wasn't fucking her, I was.

My plan had worked.

As for what Lisa thought about me wanting her to have regular sex with another man, well, she's always known that I was a board-certified voyeur. Once Steve started fucking her regularly, she began to understand my arousal at watching another man use her pussy on a constant basis. She told me more than once that she was grateful that I'd arranged for she and Steve to start fucking incessantly.

 

Even after all these years, it only just occurred to me that my wife and I were textbook examples of a stag/vixen couple, with our friend being the bull (I think) in our long-term MFM threesome.

 

Not sure what our relationship could be labeled as. But I guess we tried it all. Hot wife for sure.