[Straight Sex] Most memorable sex you've ever had

[Sonera]

Originally Posted by frodobaggins19

I dated a short, stacked blond with long hair for a couple of years in college. She had an identical twin sister. I could tell them apart but most people could not.

One weekend my girlfriend got a job house sitting for a couple who were friends of her parents.

t.

Heard of 'babysitting', and understand why the babies can't look after themselves.

But why houses?

[OPD940B]

Originally Posted by Sonera

Heard of 'babysitting', and understand why the babies can't look after themselves.

But why houses?

When late teens and early twenties I was asked to do some house sitting for families that I was friends with. (Friends parents owned the homes) Would basically take care of the interior plants, pets, aquariums, and make the homes look lived in (which they were, as i would stay there) collect mail and packages as appropriate...

i would be paid to do take care of the property and given use of the house and vehicle. Back in the 80's I would get $200 US per week and usually a refrigerator full of food. Duration would be 2-6 weeks during the summer and 1-3 weeks during the winter break. I could really clean up if I had more than one house to care for.

And it was nice to have a place to land with a date where I could play house. Most of these home had nice amenities like pools, spas, and saunas, with private yards. Had many a good times with GF's and small intimate parties.

[ChristerChrister]

Yesterday. 3 couples in their 30s, plus 2 extra men including me. Everyone had sex with everyone and it was extremely good sex. Definitely my most memorable experience.

[txrock]

The best ever sex I had was the sloppy seconds after a 29 year old black guy spent all night fucking my 50 year old wife on her 50th birthday. He cummed in her bare back 4 times and my wife didn’t have any idea how many orgasms she had. That was the start of her 7 years in the interracial hotwife lifestyle with the last 5 being black only.

[LBnJB]

Originally Posted by txrock

The best ever sex I had was the sloppy seconds after a 29 year old black guy spent all night fucking my 50 year old wife on her 50th birthday. He cummed in her bare back 4 times and my wife didn’t have any idea how many orgasms she had. That was the start of her 7 years in the interracial hotwife lifestyle with the last 5 being black only.

Similar to mine, except it was my 50th birthday, not hers. It was her idea, and she did not say a word to me before hand. After dinner, we were sitting at the bar having a few drinks. I went to the bathroom, and when I returned I saw her from across the bar, kissing a complete stranger. When I approached, she introduced us. She had told him it was my 50th birthday, and that I had always wanted to watch her fuck another man. As I sat down, my wife said to me, "he lives close, has condoms, and wants to fuck me. What do you think?" We spent three hours in his apartment. We had talked about sharing her before. She had told me if we ever did, she would not kiss him, would not suck his cock, would require a condom, and would not give up her asshole. Well, he never wore a condom, and came in my wife twice. Once in her ass and once in her mouth (yes, she swallowed). He was the first, but would not be the last (not by a long shot.....). He had a big cock, but not the biggest. He was good, but would not be the best she would fuck. But he was the first. It still gets me hard thinking about it.

[pball2295]

My favorite sexual memory isn't so much a single act - more of a bunch of intertwined ones.

I've always been pretty monogamous and never felt comfortable cheating. I was dating a girl for several months at this point. She was really the first freaky girl I'd ever been with and the first girl I ever had that loved ROUGH sex.

She lived about an hour away from me and I usually only saw her once a week.

Meanwhile, in the college town I was living in, I became friends with a group of student (guys and girls), and they adopted me on their intramural soccer team. I also hung out with them quite a bit. One of the girls -- a cute, petite little 20 year old, had a massive crush on me. I knew it all along, but never acted on it. I didn't even tell her or the others that I had a girlfriend, because I enjoyed innocently flirting with the girls - especially the one who had a crush on me.

A few months had passed since I was in the group of friends, when things started getting sour with my girlfriend. We began having breakup conversations.

At the same time, things started getting extra flirty with the college girl.

After a fight with my girlfriend over our status, I decided I wasn't going to visit her that night, and would instead go out with my friends, including the cutie crushing on me.

The night was increasingly alchohal infused and by 1 am, I was dancing dirty with the girl in a dark club. On a whim, I decided to put my hand down her skirt and gently touch her vagina. She reached down, grabbed my cock, and whispered, "I want your cock."

We bolted out of the club and into her friend's house. I tore off her clothes, ignored the condom in my pocket, and fucked her incredibly tight pussy. A few hours after we had sex, as she laid naked in bed, she told me she'd only been with one man before me. Her high school boyfriend. She also told me that she wasn't sure how to give a blowjob, and never thought she was good at it.

I told her "the key is letting the guy take control, if you're comfortable with it."

She said, "I am."

Within seconds, she was on her knees.

I slowly began fucking her throat.

She gagged a few times, looked up at me and apologized. "Sorry, she said. That's gross."

I kissed her forehead and said "no, no...I love that."

That's all she needed. She looked up at me, and began furiously gagging on my cock. She was desperate to pleasure me. I pinned her to the bed and fucked her face like it was her pussy. We started 69'ing and her pussy was soaking wet.

Finally, I told her to get on her knees, and I absolutely blasted her face with my load. She was shocked...as jizz dripped off her eyes, nose, and chin.

I cleaned her off, told her she was beautiful, and that I needed to head home. She stood in front of me naked, hugged me, and asked me when we'd see each other again. Tonight? I said. She smiled.

On the way home, I called my "technically still" girlfriend on the phone. She asked if I wanted to come over for lunch and talk.

I skipped the shower, and got on the highway.

I was so at peace from the previous night, that when we sat down to talk, all the anger had gone away. We both agreed that we should spend some time apart, just to see how it goes.

On the way back to her house I thought to myself..."you know what man...you're not cheating on anyone at this point...just go for it."

I pulled her into her bedroom and said "friends with benefits?" She laughed and I stripped her naked.

It had only been two hours since I came all over the other girl's face, and said goodbye as she stood naked - as if waiting for me to return. Now, as I looked at my recently-named ex, I compared their bodies. My ex had bigger and better tits and a thin runway strip over her pussy. She was thin-ish, but only in moderately good shape. The 20 year had an incredibly tight body, little tits, and was totally shaved.

She pulled me onto the bed and spread her legs.

But I had another idea.

I knew I was certainly a funky from the prior night of condom-less sex and no shower. So I thought to myself...hmm, let's see if she can tell what she's tasting.

I sat her up on the bed and put my cock in her mouth.

She sucked it for 10 seconds, then coughed and said, "hey! think you could shower before you put your dick in my mouth!" I said, "haha sorry, sorry. Long night of dancing."

I fucked her bareback, made her cum, pulled her up by the ponytail, and blasted on her face too.

On the way home, my dick was hard the whole time, thinking about how I just made my now ex gf taste the dried pussy juice of a girl who had a massive crush on me.

I went home, showered, slept for 5 hours, and showered again. Then I took the 20 year old out for a beer, and fucked her again.

As we made out in the shower afterwards, and she told me I was incredible.

I layed her down on the bed, took whipped cream out of my bag, and completely shocked her by licking her everywhere. Including her asshole. She never experienced anything like that.

It was an insane 36 or so hours!

Sadly, I ended up breaking the cutie's heart after a couple months of amazing sex. A few years later, I reconnected with my ex and he hooked up a few times --- totally emotion-free. Just for fun. I admitted to her what happened that night, and admitted that I wanted her to taste the college girl's pussy. She was pissed in a joking way, but called me a sick bastard and actually thought it was pretty hot.

She asked me to see the girl. I pulled up some of her hottest (clothed) pictures. Didn't want to let on that I safely protected naked shots of both of them

[25baja]

Originally Posted by Showife

The most memorable sex was also the most unexpected.

One afternoon many years ago I met up with an old friend of mine at his flat, and after several beers I started to tell him about a girlfriend that I met a few months previously. Donna was a divorcee who in her marriage had never orgasmed, yeah really, but with her newly found freedom she was chasing time to do just everything!
With my constant encouragement she dispensed with her bra and panties, had her nipples pierced, and shaved her p**sy smooth. She also took to showing like a natural, enjoying the shocked look when guys caught sight of her carefully rehearsed exposure.

She'd called me earlier that day asking if we could meet up and I'd given her my friends address, suggesting she might like to come in and have a beer. Sure enough an hour or so later the bell rang and there was Donna looking great, knee boots, jeans, and a white silky shirt that allowed full movement to her braless state, her piercings proudly poking through the material.

My fiend stood there with his eyes agog, Donna was probably a 36D, and man did it show. In she came, grabbed a beer and sat next to me on the sofa. My many beers had made me a bit over-casual with an appreciative audience so it didn't take me long to start caressing her tits, then slowly unbutton her shirt in order to show my friend her piercings. She certainly didn't mind and he loved them, and watched as I played, Donna was thoroughly enjoying the exposure and the pleasure of having her nipples pinched and pulled in front of a stranger.

Finally the beers had their way and I needed the toilet. I was only gone a couple of minutes but when I got back I saw that my friend had taken over from me in style, alongside Donna on the sofa sucking on one nipple for all he was worth, with one hand squeezing her breast and the other down just inside her jeans under her belt. I took his chair and watched then as he struggled to get further into her jeans. Easing forward I unfastened the belt, then the waist button and zip, before tugging her jeans down to her knees. My friend took his cue, rubbing his hand on her p**sy with Donna vainly trying to get her legs apart to help him. By this time I was on my knees in front of them, unzipping her boots then pulling them, and her jeans completely off. Donna's legs sprang apart and she groaned as my friends large hand shot between her legs, two fingers disappearing deep inside her. I sat back in the chair, a ringside seat to the action in front of me. Eventually my friend moved away and muttered "I think we'd be more comfortable on the bed."

My friend made his way to the toilet while Donna and I headed for the bedroom where I laid on my back as Donna took my hard cock anally, then lay there spread out ready... My friend returned and quickly slipped into her p**sy and fucked her hard. It was Donna's first DP and she took to it with a passion, and all too soon it was over. We lay there bathed in sweat but with that strange surreal shyness. Then it seemed just minutes before Donna went her way, and in the stunned silence that followed my friend and I just looked at each other... then he said "Well, it was nice to meet Donna" and burst into laughter.

Great story. It sounds like Donna was a lot of fun. Hopefully you got together often and it was always as hot

[raysallx]

I used to work with this fat girl at the U of Minnesota college newspaper. She had huge tits and a wide ass, so I was enthralled, but she always seemed to have a boyfriend.

One day I ran into her on campus. She wanted to go to a nearby wine bar to celebrate the end of the school year. We proceeded to get drunk together (no mention of her boyfriend) and told me we needed to stop at her apartment to get her diaphragm. When we got to my place there was no pretense; we went straight to my bedroom and my nose went straight to her cleavage. She commented on how she knew I liked big tits. I stripped her and her body was amazing: huge tits and nipples, big, full and round ass. I got on top of her and just pounded away while she kept saying, “Fuck me, you fucker!”

Being drunk, it took me forever to cum, although she seemed to be coming the entire time. At one point we both passed out, me still inside of her and still hard. When I woke up I just kept fucking her; she woke up and we continued fucking until I came. She fucked like a wild animal.

The next morning we took a bath together and she blew me under the water for a half hour, coming up for air looking like a drowned sea monster with running mascara, etc. Not the prettiest face, but she got an A for effort. Like an idiot, I never looked her up for a return performance. She even called me once, but i had a girlfriend who lived in my apartment and I declined. Major regret.

[jimmybob69]

I can't compete with most of the stories here, but I cherish this memory .
It's a little long because it has to do with developing trust.

Part 1

I met my current wife in early 1976. February 29th, 1976 to be exact.
I had been married five years earlier, at 21, but now I was single.
I was 26, she was 23.
She looked like Farrah Fawcett. She was naturally blonde and did her hair in the same manner as Farrah
She had never been married and, as a matter of fact, she was still a virgin.

Really. Honestly.

Her parents were strict Mormons. She had been raised as Mormon and indoctrinated in the faith. Her father was a bit domineering, and she had self confidence issues. I had self confidence issues myself. My ex-wife had been unfaithful on several occasions and finally left me for one of her other boyfriends. I should also note, for the record, I had a young son from that previous marriage and had him a lot of the time because his mother was busy reaping her wild oats.

My future wife lived next door to my older brother and his wife, and would babysit for them occasionally. They played matchmaker and that is how I met her.

Anyway, we met and began dating in mid winter. We did the dating thing for a month or so. I would pick her up at her parents house and dutifully return her at the end of the evening. We would go to movies, out to clubs, or any other things that young people would do in the mid 70's on a date. We had fun together. We boosted each others ego's. But we didn't really get a chance to make out because she lived a half hour from my house and there wasn't time to do something, make out and then drive her home and get me back home for my son when he got up.

It so happened that she worked in an office about 1/2 mile from my house. About a month into the relationship we had a late season snowstorm and the roads became virtually impassable. There was no way she could get home to her parents house. She called me from work to see if she could stay at my house with me overnight. I, of course, said yes, but she had to make me dinner. It just so happened that my son was with his mother for a week. Once she got there she called her parents to let them know she would not be driving home in the storm and was going to stay with me, at my house, overnight. Her father gave her a ration of shit (he really didn't like me because I was divorced, against their religion) and she told him if he wanted her to come home, he would have to come pick her up because she wasn't going to wreck her car trying to get home. As I said before, it was an hour round trip on clear dry roads. He decided she may have had a good point. With that drama resolved, she started making dinner while I made a fire in the steel fireplace I had installed in the living room. Those of you that lived through the 70's may remember the cone shaped steel fireplaces people put in their houses. I had one.

Dinner was over, the table was cleared, I think maybe even the dishes were clean, and it was still early. There was a lot of time left in the evening. She said, innocently, what do you want to do.. I said, well, we have a fire in the fireplace, I have this bottle of wine I've had for a while, my son is with his mother, nobody's going to come knocking on the door tonight, and we really haven't had any time in our relationship to do any making out, so......what do you think???

She said I am a virgin. I will be a virgin on my wedding day. I know you were married and have had sex. I won't have sex with you or anyone else until I have a ring on my finger. We can make out but if you do anything that makes me uncomfortable I will stop you and if you don't stop when I ask you to I will leave, even in this storm. And, I won't take my clothes off. Those are my ground rules.

She also added, I've made out with some of the other guys I've dated and to tell the truth, it never did anything for me. "I'm really not that responsive." (Note: Most of the conversations are adlibbed. I put quotes around this because it is a direct quote. I will still throw it out to her "not bad for an unresponsive woman" after an occasional multiorgasmic event).

I said, OK. I understand. Let's see what happens.

We pulled the couch over in front of the fireplace and poured a couple of glasses of wine. I put my two favorite albums on the record changer, Gord's Gold (Gordon Lightfoot) and Crosby, Stills, and Nash, the one with Suite Judy Blue Eyes. We lit a few candles, turned out the lights and sat down in front of the fire.

[jellyworm]

Come on man, don’t leave us hanging! We want more!!