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Not what I expected

Age when it happend: 19
Where it happened: Hotel
Langauge: English
Sex: Male
Rating: 5
Category: Straight

My first time was with a woman in a hotel room. I’m a guy, so naturally I think about sex 90% of the time, and I’d been absolutely obsessing over this for about two years. I finally got up enough money to go see a hooker.

They always say that prostitutes are some of the ugliest women you’ll find, and so I was a bit uncomfortable. When she showed up, though, all my problems went away. She was about 5’5, young, slim, and beautiful, only 20 years old herself. She had dark blue hair and a cute little prim-and-proper blouse; I could tell she’d not been doing this for long. She was very cute, and very meek, but she was very eager to engage me sexually. So I took her up on it.

She wanted me to go first, so I did. I took off my shirt and pants as she watched, licking her lips. She seemed nervous, so I tried to coax her into conversation. I asked her how long she’d been doing this, and she said, “Not long.” I smiled and told her I thought as much, then I asked her if she liked it. She said that some men were really nice, and she liked them—the ones that held her tight and called her name and came inside her, she said that made her feel really good. But she said there were also mean guys, the kind who liked to hit her and choke her and make her feel really ashamed of herself, and I felt kind of bad for her. If I had been able, I would have offered to help her out, but I was barely out on my own; I could barely support myself.

She got started taking off her clothes, though, and I lost control of myself. She was wearing this cute little blue bra underneath, and she took it off with expert ease. She had these cute little breasts, little Bs or Cs, it was hard to tell, and they bounced a little bit as she climbed onto the bed. She asked me how I wanted it, and I said, “Just straight-up is fine with me.” So she asked me not to come inside her; neither of us had a condom and she was afraid of getting pregnant. I asked her if there was anywhere she’d like me to shoot it when I came, and she said, “anywhere you like.” So I asked if she would like for me to shoot it up on her back. She gave me a surprised look, like she’d never heard someone ask for that before, but then she nodded and said, “sure, okay.” She got on her hands and knees and patted her pussy, telling me to “hop on up.” So I got on her and started going to town 🙂

She was pretty tight; I remember the inside of her feeling kind of rough, but it also felt good—the head of my penis was just the right size to get a good feel of her as I pumped her. And she was so beautiful….I had such a hard time not coming inside of her. I had to move very slowly to keep from going too hard and coming too fast—I paid her for a full hour, and if I came now, I didn’t think I’d be able to do anything else for at least another twenty or thirty minutes, so I wanted to make it last as long as I could. So I fucked her slowly, reaching underneath her arms to get a few good squeezes at her breasts. I tried to finger her clit, but she brushed me away because she was already doing it, and she didn’t want to waste time explaining to me how to make it good for her. I found this selflessness very attractive, and I once again had thoughts about asking her to stay with me, and stop prostituting….but again, money concerns came up. I felt bad, but the way I was going inside her (almost to orgasm), I couldn’t think straight for long. As I neared orgasm, I started moving more slowly, because I wanted so badly to keep fucking her. I put my hands on her back, just above her ass, and rode her for the last mile, watching our reflections in the blank TV screen at the end of the bed. I saw myself up on my knees, back straight, hands on her hips, pumping her, and I saw her leaned forward, her head held up, her eyes closed, her face flushed….she was gorgeous, and looking back now, I would give anything to have her back. Right before I shot it, I pulled out of her….but I couldn’t bring myself to come on her.

She asked me if I came inside her. I told her no, but she said she thought she felt it, and she got scared. I assured her that I didn’t, and she could prove it by finishing me with her hand. I told her I wanted to look at her face while she finished me. She was a bit taken back, but she agreed, except instead of using her hands, she got down on her knees in front of me and started sucking. She clearly hadn’t done it many times before; she kept using her teeth, and it hurt a little (and for several days after), and so finally, to avoid hurting her feelings, I said I wanted to finish myself. She said she’d catch the cum, and she got down under my penis. I made the last few strokes with my hand, and ejaculated right onto her face. Some of it made it in her mouth, and a little dribble of it caught on her lower lip. I remember her swishing her toungue around to get that little bit off, and I thought that was cute. I also remember that being the best orgasm I’ve ever had to date, even now. Some of it got in her eye, though, and she winced. I was afraid I’d hurt her, so I made to lean forward….but she went back for one last swoop, taking my whole erect penis into her mouth and taking the last of the cum off of it like the good sport she was.

After that, we started putting our clothes back on, and without thinking about it, I kissed her on the cheek. She acted a little freaked out, and I apologized. I said that I had enjoyed being with her so much, I wish she was my girlfriend….but I said I understand if she can’t be. I gave her the $50 we agreed upon (plus a $100 tip, for being so cute), and told her to be safe. We flagged her down a cab and I never saw her again. But if I did, I’d probably ask her to stop prostituting and live with me. She was too sweet and innocent to be a hooker. I’m just glad my first time was with her.

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