hot date (part 1)   added 6 years ago    

  By: 2tired

I'll make this one brief (without all of the dialog and such), but too the point. It's one of my favorites. Let me know what you think.
"The evening began with my meeting a surprisingly cute/hot 20-something woman at a downtown restaurant for a "get to know you a bit better" dinner. 
After about the first 15 minutes of conversation, it was mutual that the dinner was not meant to last very
long. Her outfit was very beautiful, as in it was not a very "...hey, check me out.." hot attire.
However, it was the combination of what she had on conforming perfectly to her body that got me going.
A very long, pleated skirt, with a white, button-down top. 


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Noticing that our conversation was taking a turn to finding out our individual turn-on's and off's, we
couldn't help but notice the compatibility. Not too much longer, and I noticed that she began to squirm a
bit at her seat. At first, I was concerned that there was something wrong, because she was seeming a bit
distant, but she responded that she really wanted me to take her back home, and that we could pick up her car later. 

Skip to the fact that I was in her apartment, and I was in the bathroom taking in this fact, and wondering
where this evening would go.
I heard her turn the TV on as I was washing up, and as I came out, she was relaxed on the couch with her
legs up. It was one of those long, sectional couches, and she was propped on the corner with her long legs
stretched out.
I asked if I could sit down by her, and she simply motioned that it was okay down by her feet.
Well, as I sat down and looked up at her to begin to ask if things were okay, I couldn't help but notice
that her long skirt had been "collected" in quite a tight bunch right between her legs at her crotch.
Needless to say, this sent quite a rush through the whole of me.

From there, I took off her shoes and gave her a deep rubdown. Not wanting to really push things, because
it was apparent that she was taking things right where I would want them to.
As I was rubbing her feet, she picked up where she left off while I was in the bathroom earlier. She started out by sliding her hand down the front of her skirt, the whole time staring me in the eyes.

This was making me as hard as possible while dressed...and it was noticeable as well.
I slid her long skirt up and began to massage her legs. Her legs were perfect. Thin, but extremely toned.
I mentioned to her that this may make things a little easier than trying to work her way past the top of her
skirt. From there, she pulled her skirt the rest of the way up, and spread her legs apart with the flexibility of a gymnast. I joked with her (a risky move, I'll admit) that that may make the massage a bit more difficult. She responded that she didn't really need me to massage anything else down there, as she used her two index fingers and spread her lips apart and slowly fingered her clit.

I lowered down onto the floor and began to lick around her lips, which were about as swollen as I was.
Along with that, I gently fingered her tight little ass hole, seeing how she was with that. 
She told me that she wanted to feel me inside her.
That's all it took for me to get up and take my pants off, and mounted her slowly, enjoying the moment as
much as humanly possible. The beauty of how wet she was, was that her juices were spilling down to her
anus, and she was feeling it as well.

The penetrating had gone on for close to 15 minutes, and I was feeling the buildup towards cumming gaining strength.

I told her that I was starting to get close (to cumming), and asked what she wanted, because now was the time to plan for it.
She said that she wanted desperately to feel my hot cum blast inside of her pussy, but not just yet. I
agreed, and asked her what else she would want. She hesitated, and asked if I had ever been inside
of a woman's ass.

That same rush as earlier hit me. I had not, but had really wanted to know what it would be like. 
We agreed that we would try it out. I pushed her legs back, because I told her that I wanted to still see
her face as I fucked her and came inside of her.

She held me off for a second, and reached down between the sections of the couch and pulled out a clear
Plexiglas (8" or so) dildo, and said that she wanted to be double-fucked without the hassle of two guys.
I told her that I couldn't agree more, as I really
couldn't concentrate with another guy there. I'm selfish that way, I guess.
She spread her legs apart and back near her head, exposing her soaked pussy and ass hole to me. I
motioned, "you first", and she proceeded to push the dildo between her lips, and deeper with every

"Hurry up, and get in here. I'm going to cum soon."

With that, I worked my cock's head into her anus, just past the opening, and with the help of her juices
and mine, I managed to slide my way in. It was a bit odd at first, but combined that with her reaction, it
was perfect.
After about a couple of minutes of working my way in and out of her ass hole, I pushed as hard as I could
into her and unloaded my cum into her ass, all the while watching her fuck herself faster and faster.
As she came, she wrapped her legs around me (with my cock still buried in her anus) and orgasmed harder than I've ever seen a woman cum.

Fortunately, this episode did not end clumsily, but with much talking, and even more conversation about
what may take place again. The sooner the better."

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A fantasy by:

  2tired (view profile)

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Fantasy Info:

Categories: Anal Sex
Location: No specific location | Roleplay: Other
Fulfillment: I will tell you later | Nature: Romantic