B- It was a month after I had turned 21 and I decided to post an ad on craigslist for sex (the first one I had ever posted) and B responded. I don’t have the pics anymore, but from what I remember she sent two pics. One was a face pic and another clothed full body pic. She was black, appeared to be of a lighter black complexion (she turned out to be more of an average black complexion), seemed overweight, but had a fairly cute face. At the time, being a virgin, I was just excited that there was someone out there who wanted to have sex with me, but if this girl had responded to an ad that I put out nowadays, I wouldn’t be interested. Still, I’d give her maybe a 4/10 based on the pics. Anyways, we e-mailed a bit and I got some confirmation that she was pretty up for anything including a facial which really turned me on. We agreed that I would pick her up from the metro station and take her to a hotel room that I paid for. I found a hotel room along one of the major highways where I live and it cost me $60 for the night.
As for the encounter itself, I drove to the metro station during the evening where I picked her up. As soon as I could see her from my car I was already disappointed. From what I could recall, she was wearing a purple shirt and jeans. I could also see her belly popping out from beneath her shirt which made her look really trashy. Plus, she was much fatter than the girl in the pics that she sent me. Then when she finally got in the car and I could see her up close, I was more disappointed. She wasn’t attractive. Her face looked kind of manly, not the cute looking one I saw in the emails. Her tits looked pretty big, but that was the only thing she had going for her. But for me at the time, that was enough and I was on my way with her to the hotel. While in the car, I remember telling her I thought she was very attractive. I was lying, but I thought this would help loosen me up and make her more comfortable with me. It seemed to work. The only other thing about that car ride I remember was when we got out of the car at the hotel, she asked me how tall I was. Apparently height seemed to be a big deal to her and I assume I passed her height requirements (I’m 6’3 btw).
Now on to the sex part. When we got in the hotel, I remember her asking me, “how do you want to start?”, or something along those lines. I basically responded with let me just check you out and I began to fondle her and undress her. I remember that I was sitting on the bed while she stood in front of me and began to undress her. She took her bra off and I remember tits were fairly big and much heavier than what I was expecting. But, they were also very saggy. Like if she lost weight, her tits wouldn’t be that big. She was also really fat. However, none of this turned me off or anything, but what did was her body hair. She was pretty hairy. There was just hair on her in places that you wouldn’t expect for a woman. But hey, what are you going to do?
I believe I laid her onto the bed and continued to remove her clothes. In particular, the one article of clothing I was most excited about was taking off her panties. I was finally going to eat pussy! I was so excited. Here I am, finally going to do the thing that sometimes I feel like I was born to do. So I take her underwear off and to my total disappointment, she smells awful. Absolutely awful. Like disgusting. I couldn’t go down on her. The smell was just too much. So I fingered her. Now I don’t remember this for sure, but I think I fit in 4 fingers really quickly. Like with little buildup. At the time, that didn’t seem weird. But now that I have more experience, it only leads me with the belief that she must have fairly loose to fit that much in her without much warmup at all. My fingering technique basically consisted of just jabbing my finger into her really fast. She seemed to like it. I dunno.
Once I was done fingering, it was time for my pleasure. I remember her saying that she wanted to see some of me. So I removed my pants and whipped out my dick. I remember being pretty self-conscious about this at the time because wasn’t fully hard. I even said something like, “I’m not totally hard right now”. And frankly, I wasn’t hard because this girl smelled so bad. But anyways, I walked to the other side of the bed were her head was laying (she was laying on the bed parallel to the pillows) and proceeded to place my dick in her mouth. The back of her head was laying against the bed as she looked up at me while sucking my dick. This was the first time ever having a girl put her mouth around my dick and I remember thinking to myself, “wow, this doesn’t feel like anything at all.” Like I could barely feel her mouth rubbing up and down on me. Once again, kind of disappointing but totally not her fault.
She sucked my dick for a while, and then it was time for the fucking. Now this is when the real problems begin. First, I wasn’t totally hard and it was time to put the condom on. Secondly, this is also when I realized I didn’t know how to put a condom on. And even nowadays, putting on a condom when I’m not totally hard is a struggle, so you can imagine how difficult it was for me at the time to put it on. I struggled to get it on and this made me more nervous to the point my dick wasn’t hard. And unfortunately, it didn’t help that my partner wasn't going to help me out in terms of turning me on so I was kind of screwed. So basically, from there I fucked her without being completely hard. I’d say all on all, I was fucking her at maybe 4-5 inches. I don’t even know if she felt anything to be honest. There really isn’t much to say about the fucking itself. We did a few different positions where I just pounded away as fast I could, but I dunno if she felt anything. She definitely didn’t cum at all. One thing I do remember was flexing in one of the side mirrors while I fucked her. I was pretty bored too and couldn’t feel anything during the sex so that kind of entertained me for a little.
We finished off with her letting me give her a facial like she said she would during our e-mails. This is also when I got a better appreciation of male pornstars. I had always wondered why it would take guys so long at times to bust on a girl’s face during the video. It just seemed like I would be so turned on to cum on a girl’s face that it would be easy. Well it wasn’t. It probably took me like 10 minutes to finally unload on her. At first, we started with me standing over while she sucked me off on her knees. That didn’t work. Then I moved to the bed where I laid on my back while she sucked me off. This is when I was finally able to cum on her. She took it like a champ and I felt good that I was finally able to deliver because I know she was getting frustrated.
I’m getting a little tired of this so I’ll wrap the rest up quickly. After we fucked we talked for a bit and then went to sleep. I tried fucking her again but failed because I couldn’t get hard. We had to wake up early the next morning because she had to be somewhere the next day. Overall, I could tell she was pretty disappointed in the experience and that’s fine. She probably got very little pleasure from the sex if any at all. In my defense though, she was heck of a lot uglier in person compared to the pics she sent me online. It should also be mentioned her pussy stink was still on my body 2 days later even after I had showered. It was that gross. At the time, I can’t really say that I learned much from the experience. But in more recent years, I’ve learned not to fuck anyone unless you are attracted to them. Looking back on it, I really regret the whole experience. Even though I was a virgin at the time, that’s not how I would have wanted to lose my virginity. If I could have done it over again, I would have posted more ads to see if I could find something better or paid a prostitute. But that’s it. I’ll probably write about the second girl I fucked later…
As for the encounter itself, I drove to the metro station during the evening where I picked her up. As soon as I could see her from my car I was already disappointed. From what I could recall, she was wearing a purple shirt and jeans. I could also see her belly popping out from beneath her shirt which made her look really trashy. Plus, she was much fatter than the girl in the pics that she sent me. Then when she finally got in the car and I could see her up close, I was more disappointed. She wasn’t attractive. Her face looked kind of manly, not the cute looking one I saw in the emails. Her tits looked pretty big, but that was the only thing she had going for her. But for me at the time, that was enough and I was on my way with her to the hotel. While in the car, I remember telling her I thought she was very attractive. I was lying, but I thought this would help loosen me up and make her more comfortable with me. It seemed to work. The only other thing about that car ride I remember was when we got out of the car at the hotel, she asked me how tall I was. Apparently height seemed to be a big deal to her and I assume I passed her height requirements (I’m 6’3 btw).
Now on to the sex part. When we got in the hotel, I remember her asking me, “how do you want to start?”, or something along those lines. I basically responded with let me just check you out and I began to fondle her and undress her. I remember that I was sitting on the bed while she stood in front of me and began to undress her. She took her bra off and I remember tits were fairly big and much heavier than what I was expecting. But, they were also very saggy. Like if she lost weight, her tits wouldn’t be that big. She was also really fat. However, none of this turned me off or anything, but what did was her body hair. She was pretty hairy. There was just hair on her in places that you wouldn’t expect for a woman. But hey, what are you going to do?
I believe I laid her onto the bed and continued to remove her clothes. In particular, the one article of clothing I was most excited about was taking off her panties. I was finally going to eat pussy! I was so excited. Here I am, finally going to do the thing that sometimes I feel like I was born to do. So I take her underwear off and to my total disappointment, she smells awful. Absolutely awful. Like disgusting. I couldn’t go down on her. The smell was just too much. So I fingered her. Now I don’t remember this for sure, but I think I fit in 4 fingers really quickly. Like with little buildup. At the time, that didn’t seem weird. But now that I have more experience, it only leads me with the belief that she must have fairly loose to fit that much in her without much warmup at all. My fingering technique basically consisted of just jabbing my finger into her really fast. She seemed to like it. I dunno.
Once I was done fingering, it was time for my pleasure. I remember her saying that she wanted to see some of me. So I removed my pants and whipped out my dick. I remember being pretty self-conscious about this at the time because wasn’t fully hard. I even said something like, “I’m not totally hard right now”. And frankly, I wasn’t hard because this girl smelled so bad. But anyways, I walked to the other side of the bed were her head was laying (she was laying on the bed parallel to the pillows) and proceeded to place my dick in her mouth. The back of her head was laying against the bed as she looked up at me while sucking my dick. This was the first time ever having a girl put her mouth around my dick and I remember thinking to myself, “wow, this doesn’t feel like anything at all.” Like I could barely feel her mouth rubbing up and down on me. Once again, kind of disappointing but totally not her fault.
She sucked my dick for a while, and then it was time for the fucking. Now this is when the real problems begin. First, I wasn’t totally hard and it was time to put the condom on. Secondly, this is also when I realized I didn’t know how to put a condom on. And even nowadays, putting on a condom when I’m not totally hard is a struggle, so you can imagine how difficult it was for me at the time to put it on. I struggled to get it on and this made me more nervous to the point my dick wasn’t hard. And unfortunately, it didn’t help that my partner wasn't going to help me out in terms of turning me on so I was kind of screwed. So basically, from there I fucked her without being completely hard. I’d say all on all, I was fucking her at maybe 4-5 inches. I don’t even know if she felt anything to be honest. There really isn’t much to say about the fucking itself. We did a few different positions where I just pounded away as fast I could, but I dunno if she felt anything. She definitely didn’t cum at all. One thing I do remember was flexing in one of the side mirrors while I fucked her. I was pretty bored too and couldn’t feel anything during the sex so that kind of entertained me for a little.
We finished off with her letting me give her a facial like she said she would during our e-mails. This is also when I got a better appreciation of male pornstars. I had always wondered why it would take guys so long at times to bust on a girl’s face during the video. It just seemed like I would be so turned on to cum on a girl’s face that it would be easy. Well it wasn’t. It probably took me like 10 minutes to finally unload on her. At first, we started with me standing over while she sucked me off on her knees. That didn’t work. Then I moved to the bed where I laid on my back while she sucked me off. This is when I was finally able to cum on her. She took it like a champ and I felt good that I was finally able to deliver because I know she was getting frustrated.
I’m getting a little tired of this so I’ll wrap the rest up quickly. After we fucked we talked for a bit and then went to sleep. I tried fucking her again but failed because I couldn’t get hard. We had to wake up early the next morning because she had to be somewhere the next day. Overall, I could tell she was pretty disappointed in the experience and that’s fine. She probably got very little pleasure from the sex if any at all. In my defense though, she was heck of a lot uglier in person compared to the pics she sent me online. It should also be mentioned her pussy stink was still on my body 2 days later even after I had showered. It was that gross. At the time, I can’t really say that I learned much from the experience. But in more recent years, I’ve learned not to fuck anyone unless you are attracted to them. Looking back on it, I really regret the whole experience. Even though I was a virgin at the time, that’s not how I would have wanted to lose my virginity. If I could have done it over again, I would have posted more ads to see if I could find something better or paid a prostitute. But that’s it. I’ll probably write about the second girl I fucked later…