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Memorable Sex From Behind

I might have mentioned this before but here's a repeat on my best sex from behind. Wife and I and our friends made up this stupid game like Monopoly except all spots on the board were sexual. (Adult Beverages helped). Always at some point after a couple daisy chain combos, he and I had our wife's ass to ass in front of us. We were going to town on our own wife when we looked at each other and did a quick switch and started fucking each other's wife. Was our first actual swap (fuck) one of many from that point on.
 
Sgts19 said:
I might have mentioned this before but here's a repeat on my best sex from behind. Wife and I and our friends made up this stupid game like Monopoly except all spots on the board were sexual. (Adult Beverages helped). Always at some point after a couple daisy chain combos, he and I had our wife's ass to ass in front of us. We were going to town on our own wife when we looked at each other and did a quick switch and started fucking each other's wife. Was our first actual swap (fuck) one of many from that point on.
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How did the wives enjoy the swap?
 
I don't have a special memory like that, but my wife does. In her 30s, when she was having sex with others with my permission, she had been flirting with a younger man who made sales calls on her office. The were at a big picnic/concert, standing in back of the crowd, when he started fondling her boobs under her shirt. She wasn't wearing a bra. She made him stop. He pulled up her skirt, pulled down her panties, and stuck his hard cock into her pussy from behind. Nobody could see them, and he was thrusting, just letting it stay still inside her. Finally, she told him that he had to get a condom, so they went to his truck. He put on a condom, pulled off her panties, and fucked her from behind as she leaned over the console in his Ford truck.
 
Like several here have noted, I've had a few such experiences but one does stand out in my memory.

As my marriage was grinding to its last weeks, due in large part to my wife's indiscretions, I felt the need to go out and have some fun for myself as it had been a long time without sex. I met a woman through an early (back in the late 1990s), online dating app. After exchanging some messages, we met for dinner. We hit it off immediately. She was tall, small and firm B cups, and a full, firm ass, all topped with piercing eyes and a husky, sexy voice. The meal was short but our make-out session in the car was long, hot, and steamy. Our next meet up was a continuation of the first, but we quickly lost our clothes and had a log session of hot, animal sex.

It was our third time together where I was able to take her from behind. She came to my midtown, NYC office on a mid-teens floor near Grand Central Station around 6PM. Things were just as hot as before, as she stared into my eyes while giving me the best blowjob of my life. It was then, I got a true sense of her exhibitionist side. I led her to the floor to ceiling windows in the conference room, looking out at the offices across the street, some of who which were still occupied. She looked at me and ordered me to fuck her against the window. I pushed her torso forward so her gorgeous breasts were against the window and I slipped my still wet cock into her dripping pussy from behind. Slowly, we got the angle and then the rhythm just right, and I pounded away, loving those sounds of my cock sliding in and out of her soaking pussy and my pelvis slapping against her ass. As I had cum just a few minutes before, I was able to last a good long time, sometimes pulling out everything except my cock head to chill a second before pushing back in. As we were panting and sharing some dirty talk, we both looked up to see that in a couple of the offices across the way we had 5 or 6 people watching us. That set us both off. She quivered and moaned before dropping to her knees and telling me to paint her with my cum. Not wanting to disappoint her, I sprayed 5 or 6 good ropes across her face and breasts. I lifted her up and presented her to our audience who were now clapping. I think that turned her on even more, so we turned out the lights and had another round on the conference room table before cleaning up and getting dressed.

I found out that night that she lied and was married. But after we met, she knew I could help her realize her deepest sexual desires. We didn't see each other after that. But about 3 years later, she was divorced and reached out, and we continued a steamy FWB affair for several years. I really wanted a LTR with her at that point, but now that she was free and single again, it wasn't her desire. I was crestfallen but we had some wild times which I can look back on.
 
My most memorable was taking my first wife from behind while I watched her eating pussy for the very first time. I was laying on her back, and our heads were side by side, giving me an up close view of the events, I wish we had video of it.
 
Two come to mind. We are mostly missionary or spooning. The first time was when we were fucking doggy. My wife's pussy is like magic. Tight and wet, it just hugs to right. She was fucking me back so I filled her up with cum. I steadied her up so we were kneeling upright, my spent cock still in her. I started working her nipples and rubbing her clit. She came hard and squirted all over my side of the bed. It was dark so I couldn't see, but god I heard it come out with such force. She was embarrassed, but i had never been more turned on by her. The second time was her riding me reverse cowgirl fucking me. We both came and I remember her saying" is this sex in your 30's?" She then says," that's the best sex she's had". Then adds/corrects "the best sober sex". Now we don't get drunk and she's not one to talk about her past so I can't help but imagine her getting pounded away and going wild.
 
My wife and I were in NYC and we had a room with windows to the skyline. We got i to it and I had her face and tits on the glass as I was driving her from behind. A very fun and memorable experience. I hope someone enjoyed the show!
 
Forgive me if I’ve told this one before.

My last gf before the wife was in college. She was a short, very busty coed who, for whatever reason adored me. I used her for sex until my conscience started to bother me. And she wanted to stay with me! Go figure.

However, when we were together, I tried to experience as many of my fantasies as I could since she didn’t say no (other than involving another woman or anal).The most memorable of these times we were in her apartment, fucking on her bed. We had started with me eating her pussy and giving her an orgasm or two, then I fucked her missionary, got her to ride me, and finally, from behind, doggie-style.

In addition to DD tits that hung down to her navel, she had a sweet round ass and I loved to grab those hips and pound the shit out of her. She would come and come as I would reach around and rub her clit or cup those to monster tits as they hung and swayed as we fucked. Then I looked up and saw that there was a mirror perfectly positioned in the corner of the room to give me a cinematic view of the two of us fucking. And I have to say, it looked like a pretty hot porn!

I had never watched myself fuck before and it was kind of cool. But the best part was seeing her as she took my cock on all fours. Those tits looked so amazing as they bounced and moved. Her face was a mask of pleasure, half out of it from a half dozen orgasms. I could even see my balls slapping at her pussy as I fucked her. I told her to hold my balls and Watching her reach down and give them a squeeze was enough to make me blow my wad deep in her cunt. Not bad.
 
Was seeing this busty blond MILF. Spitting image of Cory Chase. The face. The hair. The body. The tits. She even sounded like her when she talked a bit.

Back at her place after a daylong date and we were fucking in her bedroom after teasing all day from a roadtrip. Sex was hot and with her fit busty body, she was a great little fuck.

Im behind her with a condom and giving it hard. Edging so nicely and enjoy the view as I was greedily fucking her for as long as I could. She was bent taking it all from me and I’m pretty sure there was a well placed mirror we were both enjoying. My load was building and after a daylong date of sexual flirting I was built up and quite full. Finally ready to bust. I climax and shoot……. FUCK!!!!

What feels like a thousand little needles jammed in my prick. It fucking hurts and my cock keeps cumming which only makes the pain worse. I pull out with a yelp and run to the bathroom as im still shooting but good God it hurt. She freaks out and asks what’s wrong but I dont know. It was freaking us both out.

I run to the bathroom and carefully pull the condom off but my cock hurts so bad it stings. Theres a little blood in it and my mind tries to figure out what the hell happened while still in terrible pain.

Somehow the condom was put on too tight or I was fucking her so hard for so long I fucked it back tightly over my shaft, but when I ejaculated there was no room for my semen to go so it shot back down my cock. Imagine fucking cumming with your cock slit pinched close. It tore up the inside which is why it was bleeding. Cum spurting out as the previous shot was getting jammed back in. Jesus Christ!

That’s never happened before and never has since. But I was pissing blood for a week afterwards and my cock was super sore and ginger.

Crazy right?
 
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Most memorable - for several reasons - was standing doggy on a staircase. We got the idea from a porn movie. Her townhouse had a long staircase that was wide enough for her to stand in the middle & brace her palms against the walls. It was very hot - until her hand slipped and we both lost our balance an tumbled to the bottom. No one hurt, fortunately, but it put an end to our fun for the rest of the night and several days after. As is often the case, it’s not quite as simple as the porn films make it look. I’m shocked.

We tried it again a few weeks ago later and got it right that time. Good time had by all and all of that. We tried it a couple other times and had quite a bit of fun. We even tried it facing up the steps instead of down. Much safer, lol, but trickier logistics.
 
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Mostlyherefortheporn said:
Most memorable - for several reasons - was standing doggy on a staircase. We got the idea from a porn movie. Her townhouse had a long staircase that was wide enough for her to stand in the middle & brace her palms against the walls. It was very hot - until her hand slipped and we both lost our balance an tumbled to the bottom. No one hurt, fortunately, but it put an end to our fun for the rest of the night and several days after. As is often the case, it’s not quite as simple as the porn films make it look. I’m shocked.

We tried it again a few weeks ago and got it right that time. Good time had by all and all of that. We tried it a couple other times and had quite a bit of fun. We even tried it facing up the steps instead of down. Much safer, lol, but trickier logistics.
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Fuck I’ll have to try being fucked on a stair case 💦
 
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