Fondest Sexual Experience

[bobb_sledd]

As I was leaving work, I texted a favored pay4play provider to arrange a quick blowjob on my way home – her place was conveniently located on my route home. She responded that she was in a multi-hour session with another client. When I texted that I I’d hit her up tomorrow she came back that if I meet her outside her buildings business office, she’d fit me in with a quick BJ in the parking lot. Fifteen minutes later I pulled in, picked her up, and drove across the street into a Starbucks parking lot, parking in the back corner. Turns out she told her date she needed his “donation” so she could go down to the office to pay her rent. She had told him me texting was the office pestering her for the rent. A quick blowjob later I was on my way home and she was on her way back to her place to finish with her date. As an added benefit, she did the deed for free, since I was such a good customer.

 

[zoso682001]

For me, it would be first time my wife and I had a 3'sum. Which was the first time she had sex with someone other than me. Some 45 years later it still gives me the sweetest memories of the most magical moment..

I'm with you on every detail !

 

[phunkyphresh]

few years back i met a young woman, 22, online. we matched and started sexting almost immediately. it started when i said i loved cooking, and she responded by saying she'd love to suck me, wearing nothing but an apron, while i cooked.

i am divorced (never married) with one child, 17 at the time. split households.

she came over the next night. at first it was the usual awkward first date sort of vibe, especially given the age gap. its pretty vanilla to this point, she stays the night. great foreplay, trading oral and fuck a few times, then fall asleep.

the next morning i wake to her playing with me, then sucking me. we move into missionary, then she gets excited and says do me doggy, so we do that... then she wants it up against my bedroom window, so we do that. her libido is crazy high. she says, "i just love doing it all over the house, bend me over your couch."

this goes on for another 45 minutes or so. all over my apartment, in every position you can think of. she was a freak and i loved it. such fun.

especially because all the while there was the thought in the back of my mind that my kid might random stop by my place.

 

[BiCanuckGuy]

It’s hard to choose a favourite when there’s so many to pick from. At the moment it’s probably the time I was in another city and looked up a nurse who I had been on a course with a while before. She invited me to her house for waffles, and 15 minutes after I arrived she had me laying naked on my belly on her bed with her tongue up my ass while stroking my cock. I knew she was special then and there. I never did get the waffles though.

 

[vandelayatx]

few years back i met a young woman, 22, online. we matched and started sexting almost immediately. it started when i said i loved cooking, and she responded by saying she'd love to suck me, wearing nothing but an apron, while i cooked.

i am divorced (never married) with one child, 17 at the time. split households.

she came over the next night. at first it was the usual awkward first date sort of vibe, especially given the age gap. its pretty vanilla to this point, she stays the night. great foreplay, trading oral and fuck a few times, then fall asleep.

the next morning i wake to her playing with me, then sucking me. we move into missionary, then she gets excited and says do me doggy, so we do that... then she wants it up against my bedroom window, so we do that. her libido is crazy high. she says, "i just love doing it all over the house, bend me over your couch."

this goes on for another 45 minutes or so. all over my apartment, in every position you can think of. she was a freak and i loved it. such fun.

especially because all the while there was the thought in the back of my mind that my kid might random stop by my place.

Love this

 

[stiv837]

One of my favorite sexual experiences was right after my first wife left me. One of her married friends stopped by to see how I was holding up and we had sex . We ended up having an affair for a few months. I don't know which I liked more , the fact she was my wife's friend or that I was having sex with another man's wife.

 

[Nellie60]

One of my favorite sexual experiences was right after my first wife left me. One of her married friends stopped by to see how I was holding up and we had sex . We ended up having an affair for a few months. I don't know which I liked more , the fact she was my wife's friend or that I was having sex with another man's wife.

You are correct. I just thought abt it and both are hot situations but here you had the best of both worlds. Which did you think abt the most during those few months would be your answer.

 

[bumpinthenight2022]

Two main memories I can think of. The first, I was at my grandmother's house, it was kinda a small family reunion kind of thing, not planned, just a bunch of her kids and grandkids happened to be there at the same time.

I have a 1st cousin who is much older, he's married to a woman and that woman brought a child into their relationship, so this girl is my 1st cousin, once removed, by marriage (not blood related in any way, we're black, she's white). I've never seen her before but she's cute, perfect little body. As cousins normally do, we get together to be mischievous and like 6 or 7 of us go for a walk, smoke, laugh, eat. By the time the walk is over, me and my "not cousin" (let's call her J) are damn near hip to hip. Grandma's house is huge, big enough that everyone can be in there and relatively disconnected from each other. So me and J steal away to a secluded part of the house and we just cuddle and watch TV for a few hours. She's pressing her ass into my crotch, I'm playing with her pussy, but everything is over the clothes because we're afraid of getting caught.

But that night, she came to my room and she was so ready she was dripping. I got the best head of my life that night. She made me cum in her mouth 3x, back to back. I literally begged to know what she was doing to me to get my body to recover so quickly. When we switched to fucking, she made me cum in her two more times. I was completely spent. I'd never been so turned on that I could just keep going like that. We actually cuddled for the rest of the night again, she got up early early and went back to her room to shower and start breakfast.

The next day, we were locked in. We fucked on top of one of the washing machines, went back in that secluded den and fucked there, on one of the bars, etc. she was constantly giving me head or I was eating her out. We went off in the woods together and fucked against some random tree. We were filthy and pretty much avoided everyone else. I'm sure the smell of sex was all over us.

And i never saw her again. Even though me and her step dad are first cousins, even he and I have only seen each other two or three times in our entire lives. At this point I'm time, J and I were ~19. Now that I'm nearly 40, I still remember that as the best two days of sex I've ever had.

~~~~~~~~~~~~~~~~~~~~~~

A different story is with my now ex wife. We were around 20 just kinda having "regular" sex but we were in this strange kinda flow. I was fucking her really good, we were falling off the bed but so into it, it didn't matter. She came a couple of times but this last time, as she was halfway stretched over the bed, her big ass titties rippling with every thrust, she started begging and screaming for me to stop -- not for fear of falling, I was bracing her very well, she thought she had to go to the bathroom. At this point, I know what squirting is but I've never caused it, so I'm like "no baby, stay with it" because I think that's what's going on but I don't know for sure, but she insists I stop, no means no so I do and when I pull out, she kinda goes into this trance and is still burning with so much desire that she's humping the air for a second. Finally she gets up and like I thought, doesn't have to pee anymore. I think about it from time to time that I wish I had just pounded her through it to open those flood gates. We still had great sex but never as great as that.

Sadly, with my current wife, we've never had anything close to that. My current wife is prettier, by a mile, not that my first wife was shabby, everywhere she goes, guys still want her. My current wife is just on a whole 'nother level. Instagram Baddie type fine. I'm just convinced at this point that beautiful women have always had it so easy in dating that they never really had to develop the skill to be good at it, including sex. Imagine being so pretty that you can't really go anywhere without guys tripping over themselves to speak to you. I'd imagine you'd go a lifetime experiencing "new relationship energy" kind of sex where the guy is gladly doing everything and it's easy for him because it's "new pussy." Sex moreso "happened" to her or was performed for her and she didn't have to really do much to have a good time. Thats fine when you're just dating, sucks as a recipe for intimacy in a marriage. The sex is just, and has always only been, "cool." Less of an exchange and more her wanting me to give her an orgasm, which, if that's all we're doing, becomes less fun and more work.

 

[Italianstud59]

When a stripper friend of mine surprised me and brought her GF was one. The other was Italian girl I met in Vegas. We went home after dinner(first date) and boy she could take it and take it lol

 

[Baztrachian]

I was in LA in 1983/1984 with my first wife (girlfriend at the time) and we were walking by some trendy bar when a visibly drunk couple came stumbling out. The girl fell over and I grabbed her to catch her fall. In doing so I had handful of a very soft and very pleasant braless tit.

I helped her to her feet and into their waiting car, her boyfriend didn't even notice.

The girl was Melissa Gilbert and the boyfriend Rob Lowe.

Ironic it was because the very first time I got to hold a tit it was Melissa Gilbert's.

 

[Italianstud59]

I had several that would listen to mine and share theirs. Always led to better sex. Talking about things she liked or was proud of made her wet. I usually got more into details of what I thought made them cum harder which made me fully erect. Same as being with a woman and her letting me know something was the first time it happened or first time she did it...

i agree! the more i told her,the wilder the sex!!!

 

[lowcollar]

Maybe the first time I crossdressed? She made me up with eye shadow and lipstick. I wore all pink with nylons, a bra and fake breasts. It was the first time I sucked a strap on dildo. She called me a cunt, pegged me and eventually with some time was able to fist me. I felt like such a slut and came so hard as did she. I sucked the strapon and tickled her clit repeatedly. We spent nearly two and a half hours in the bedroom.

 

[AllenJames]

One of my favorite sexual experiences was right after my first wife left me. One of her married friends stopped by to see how I was holding up and we had sex . We ended up having an affair for a few months. I don't know which I liked more , the fact she was my wife's friend or that I was having sex with another man's wife.

Oh, yes. After my first wife and I divorced as I was going to an overseas posting, I returned two years later and started hanging with many of the same friends including her best single friend. She made the serious first move and we were quickly friends with benefits. Since we lived within walking distance we were quickly having more sex than I’ve ever had before or since and often stayed over at the others flat. I wish I had encouraged her more to explore things with me as she would have been a great partner for that. She broke off the relationship telling me that my exwife was pressing her about what was going on. I did know that she was really waiting for her now husband to finally decide but it was quite a ride while it lasted. I still find snap crotch teddies very arousing.

 

[PersonalFavors]

Oh, yes. After my first wife and I divorced as I was going to an overseas posting, I returned two years later and started hanging with many of the same friends including her best single friend. She made the serious first move and we were quickly friends with benefits. Since we lived within walking distance we were quickly having more sex than I’ve ever had before or since and often stayed over at the others flat. I wish I had encouraged her more to explore things with me as she would have been a great partner for that. She broke off the relationship telling me that my exwife was pressing her about what was going on. I did know that she was really waiting for her now husband to finally decide but it was quite a ride while it lasted. I still find snap crotch teddies very arousing.

Mmmm. You said snap crotch teddies.
My third lover fit those nicely. She was my boss and loved my interest in her pussy. Some days just two snaps. Others 2 snaps and pull the panties aside for my mouth to find its mark. I loved coming back I got the office with the smell of her still on my face.

 

[HotwifeBrooksideKC]

The day of my 22nd birthday. I was in a giving mood

 

[Diann_Mom]

As a woman who has enjoyed quite a few sexual partners there were three or four men that were memorable, but none quite compared to the man that turned out to be my second and current husband.

I'll just say for now that he really rocked my world later on that evening of our introduction and still does to this very day.

 

[PersonalFavors]

As a woman who has enjoyed quite a few sexual partners there were three or four men that were memorable, but none quite compared to the man that turned out to be my second and current husband.

I'll just say for now that he really rocked my world later on that evening of our introduction and still does to this very day.

I wish I clicked like that with my long term partner. I miss those feelings.

 

[ladventures]

My college roommate was dating a girl and I was hanging out with her roommate out of convenience. She and I were both in long-distance relationships, so we knew we wouldn’t end up dating. But she was cute and fun, and we flirted and danced. One night we were at the girls’ apartment and my roommate and hers went to the girls’ shared bedroom.

The cute roommate joked that she would have to sleep on the sofa. I told her she could crash at our place. We went to my place and ended up making out. She told me: “This is fun, but we can’t have sex. I love my boyfriend.”

“No problem. You can sleep in the other bed.”

She thought about it and said - “Well, let’s go to your bed, but just to cuddle.”

The cuddling was going very well, as we made out and I teased her with my fingers. After a while she whispered in the sexiest, most desperate voice - “Please get a condom.”

I did as I was told. She took control and rode me. I rubbed her clit while she rode. I guess her boyfriend didn’t do that for her during penetration. She clearly enjoyed it. Her orgasm surprised her. She kept saying “Oh my God. Oh my God,” louder and more surprised by her body’s reaction.

She came and took a minute to recover. She fell on my chest and she was breathing really hard. She said - “That was my first orgasm.”

I was very surprised and proud that I got her off. I was still rock hard inside her. She begab riding again, and the “Oh my Gods” started again. Her second orgasm was more intense, with her whole body shaking for more than a minute.

Again she needed a while to recover. When she was ready she flipped us over so we were in missionary and kissed me. “Fuck me hard. I want you to cum.”

We were looking into each other’s eyes and she looked so satisfied, it was a huge turn on for me. I came really hard. And told her how good she felt.

The next morning, she had the female version of post-nut clarity and told me that was very fun, but we couldn’t do it again. She loved her boyfriend.

Of course, we were horny college students, and we broke that vow many times and we the next few months. But nothing compared to that first time when she had her first two orgasms.

 

[Nellie60]

I was at a party many years ago hosted by this couple in the thirties. I was probably mid twenties at the time. As the night progressed, I was the last man standing and the other guests had already left. I was a bit pissed but not to be oblivious to what was to happen next. I clearly hit the jackpot that night.

I was chatting with the host and his lady when she took a fancy towards me running her fingers up and down my arm while I chatted to him. He wasn't slurring his voice or that drunk as to not notice his girl coming on to me, though he still had a whisky in hand.

Anyway to cut the story short, she had grab my hand leading me to the couch while he sat back on the opposite single seater with whisky in hand. She was a nice looking blonde with an exquisite petite frame, someone I would probably be attracted to in all other situations.

She looked at me and just rested her hand on my ever growing lump between my legs then she proceeded to make out with me. Then after a little hesitation, a dirty smirk appeared on her face and she proceeded further

This lead to one of the hottest enthusiastic hand action I have ever received.

I still remember everything she said. As I was about to cum, I whispered to her "Oh yeah make me cum!!" To which she just repeated "Make me cum...make me cum" with excitement.

I told her to go faster, which she did and that's when the poor fellow walked out, clearly not able to stomach the reality of what was happening to my overwhelming pleasure.

 

[Pabiporffor]

For me, it was just a simple thighjob. I was a virgin at the time, but I had done a couple of BJs, so I wasn't entirely naive. Fun as they were, they only lasted a few mins. The thighjob was the first time I'd been fully naked with a man in bed. He was more than a few years older but still attractive. I admit I was a little nervous, but knowing I wasn't going to be penetrated really helped me to relax.

Unlike the BJs where the guys were just interested in spray painting my tonsils, I was with a guy wanting to give me pleasure as much as have his own. It was unrushed with a ton of foreplay and as I grew more and more aroused any nerves I had slipped away.

The actual sex part was a mix of having him trapped between my thighs or with my legs apart and him simply gliding along the valley, I found the second far more pleasurable and not too different to when I'd rub myself although a lot more intense and intimate.

He finished with my legs pushed back, and squeezed together as he leaned over me. I felt him trembling, and things got kinda sticky. After a quick clean up, I experienced my first oral sex to orgasm which admittedly didn't take long. Apart from the orgasm what made it my fondest experience was it really boosted my sexual confidence and trust in men.