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First "Date" Sex

CBHunter

CBHunter

Literotica Guru
Joined
Jul 10, 2013
Posts
1,335
Ever had sex with someone you just met?

One of the several times I've had a profile on AFF, I got a message that just said, "You'll do." I replied, we texted a couple of times and met at a hotel the next day. Within five minutes after she arrived, we were both naked on the bed. We met like that several times before going our separate ways. I loved sending her home to her husband with her pussy full of my cum.

Don't be shy. Tell us your first "date" story.
 
Any time I've met a woman irl that I first knew online, it was always sex on the first real date.
Usually within the first hour. :D

Kinda hard not to jump into sex when you meet someone from this website. :devil:
 
Only once did I get a girl naked on our first date. I had known her for years but asked her out one night. We ended up parked and naked in the front seat of my truck. Cops ended up driving by before we got completely going but had a good time with her. Some of the sweetest tits I've ever played with
 
EctoJohn said:
Any time I've met a woman irl that I first knew online, it was always sex on the first real date.
Usually within the first hour. :D

Kinda hard not to jump into sex when you meet someone from this website. :devil:
Click to expand...

Had the thrill of doing that with 4 different women. Met all 4 online over a period of just about one year, and remarkably, spaced about 3 months apart. All 4 women were married at the time and so was I.

After a few weeks of chat/emails we would decide to meet. When we did there was no doubt as to what it was going to be about... right to a motel room. By previous agreement, each of the 4 women and I swapped underwear as 'souvenirs'.

There were two things that made these encounters a turn on for me:

1. I got away with all 4 of them. To this day, my now long ago ex-wife, has not a clue they ever occured.

2. The fact that each of them were married at the time. There is something about the realization that you are fucking some other man's wife that is a powerful turn on. You are benefiting from that man's neglect of his woman. And I was lucky. All 4 turned out to be attractive, intelligent women in search of a few hours of 'escape' from the misery they lived in. No strings, just fun sex.

Did I feel any guilt? Not really. At the time these meetings occurred, my marriage was dying, in part because I was suspicious that my wife was cheating as well.... with other WOMEN. Sure enough she was, and about 6 months after my encounters, she left me for one of her 'girlfriends'.
 
Last edited:
secret_passion49 said:
Had the thrill of doing that with 4 different women. Met all 4 online over a period of just about one year, and remarkably, spaced about 3 months apart. All 4 women were married at the time and so was I.

After a few weeks of chat/emails we would decide to meet. When we did there was no doubt as to what it was going to be about... right to a motel room. By previous agreement, each of the 4 women and I swapped underwear as 'souvenirs'.

There were two things that made these encounters a turn on for me:

1. I got away with all 4 of them. To this day, my now long ago ex-wife, has not a clue they ever occured.

2. The fact that each of them were married at the time. There is something about the realization that you are fucking some other man's wife that is a powerful turn on. You are benefiting from that man's neglect of his woman. And I was lucky. All 4 turned out to be attractive, intelligent women in search of a few hours of 'escape' from the misery they lived in. No strings, just fun sex.

Did I feel any guilt? Not really. At the time these meetings occurred, my marriage was dying, in part because I was suspicious that my wife was cheating as well.... with other WOMEN. Sure enough she was, and about 6 months after my encounters, she left me for one of her 'girlfriends'.
Click to expand...
Couldn't agree more with your assessment #2. I love knowing that a married woman is turning to me to get what her husband can't or won't give her
 
coacheric said:
Only once did I get a girl naked on our first date. I had known her for years but asked her out one night. We ended up parked and naked in the front seat of my truck. Cops ended up driving by before we got completely going but had a good time with her. Some of the sweetest tits I've ever played with
Click to expand...
Did you two get together on a later date?
 
Sure, but I grew up in the late sixties and seventies and eighties!

Hell, I fucked some and never did know who they were...

This was before HIV & Aids and a host of other really bad shit!
 
I've had sex with first dates plenty of times. Also with randomers who are flirty and sexy :devil::D
 
Met this gorgeous boy quite many moons ago now... Ended up shagging him in his hotel room. It was at times a bit clumsy and slightly awkward, but my god I've never been as aroused during "first sex" as I was back then. He lit me up in flames with his beautiful face, lanky yet gracious soft body, amazing thighs and juicy, fat cock... I actually came when he pushed himself inside me, right then and there :eek: My body was made for his. It wasn't the best sex I ever had, but it was special in a nameless way.

.....and yeah. We ended up together, married and all the rest.
 
MissJW said:
Met this gorgeous boy quite many moons ago now... Ended up shagging him in his hotel room. It was at times a bit clumsy and slightly awkward, but my god I've never been as aroused during "first sex" as I was back then. He lit me up in flames with his beautiful face, lanky yet gracious soft body, amazing thighs and juicy, fat cock... I actually came when he pushed himself inside me, right then and there :eek: My body was made for his. It wasn't the best sex I ever had, but it was special in a nameless way.

.....and yeah. We ended up together, married and all the rest.
Click to expand...

Awwwwwwww :)
 
had a threesome with a girl I just met. SHe was a friend of my GF at the time. She warned me than this girl was a complete nymph but I had no idea just how much until I actually met her. We stopped at her apartment for some odd reason or another. Not five minutes after we are in the door, she looks at my GF and says "hey, have you had sex with him? Because I would love to have sex with him, but not if you haven't had sex with him yet". As a joke I reply, "we can always have a threesome and get it all done in one shot". Apparently she didn't think it was a joke, and without hesitation, she whipped her shirt off and said OK! I was stunned. My GF, who was more familiar with her friend's sexual appetite, only took a few moments to decide to go with it. I was actually the one who took some convincing. My first instinct was that this was some kind of trap that I would somehow be blamed for. the joys of being 18 and being not to bright about the ways of the world. I did have sex with both of them throughout the night and never spoke a word of that night again to each other.
 
MissJW said:
Met this gorgeous boy quite many moons ago now... Ended up shagging him in his hotel room. It was at times a bit clumsy and slightly awkward, but my god I've never been as aroused during "first sex" as I was back then. He lit me up in flames with his beautiful face, lanky yet gracious soft body, amazing thighs and juicy, fat cock... I actually came when he pushed himself inside me, right then and there :eek: My body was made for his. It wasn't the best sex I ever had, but it was special in a nameless way.

.....and yeah. We ended up together, married and all the rest.
Click to expand...

Awwww :heart:
 
I'm game, so long as it's understood that thumping the headboard does not necessarily equal a repeat performance on another night.
 
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