My first time is kinda hard to explain. I had seemingly given up all hope of ever getting laid just a few short months before. I had never had a girlfriend before and was painfully shy to talk or approach girls I didn’t know. I was living in a new city and it was a very lonely time for me. Then, out of the blue, I started talking on the phone with a girl I had BRIEFLY met the previous summer in a city that I go and visit every year where my relatives live. She had remembered me from us meeting at a show the previous September when a friend of mine was introducing me to all his friends. She found my e-mail address somewhere and e-mailed me out of the blue one day to ask me a question about an album I had. From there, we were pen pals for about a month, getting to know each other a little better, sending mix-tapes to each other, that kind of stuff. Then, we started talking on the phone almost every night (she has a kick ass long distance plan where you get unlimited long distance hours evenings and weekends all across the country) and through the realization that we had a shitload of things in common with each other, we started to really like each other.
A few little problems, though. She lived in city 12 hours away from mine that I only visited once or twice every year (to see my aunt and uncle) and she was older. After some doubt as to whether or not we’d be doing the right thing entering a relationship with each other, we decided to say “Fuck all that” and go through with it anyway. I was going to be there for the summer anyway, so why not?
The day came that I was going to see her again and finally really get to know her. I took the train there and she was there to meet me at the train station. I was nervous as hell, didn’t want to get off the train, but I bit my lip and went through with it. Luckily, she was just as nervous as I was and that made the situation a little bit more comfortable as we could feel each other out a bit more. I gave her a hug, we picked up my bags and went back to the apartment I was going to be staying in for the summer (which she helped me get).
As we walked back to the apartment and talked, we realized that being together really wasn’t that much different than talking on the phone. We didn’t need to be nervous around each other because we really knew each other and had for a few months. There was still a lot of tension and awkwardness, but it was not hard at all to overcome it.
We got back to my apartment, plopped my bags down and sat down next to each other on my bed for awhile. I wanted to kiss her so bad, but I was too nervous to do anything (after all, I had never made out with a girl before, either). She looked really nervous, too, because she knew I never had too and wanted me to get it over with. So I, I sucked in my gut and looked at her and said “can I kiss you?” and she said “yes. I’ll help you” and I leaned over, paused for a a kissed her. She helped me a little bit, leading me into opening my mouth and whatnot. We ended up making out for over an hour, like two junior high kids. She told me a few weeks later that I was really bad at kissing the first few times we made out, but got really good at it pretty quickly. We only stopped so we could go out and get some supplies for the apartment.
When we went over to the mall on the bus, we held hands the whole time. The nervousness turned into comfort and I could tell she was comfortable, too. But at the same time, the excitement that I was FINALLY with a girl gave me a few…uhhh… problems keeping a certain part of my anatomy at bay. I had to keep covering and tucking away my dick so no one would see I had a boner and the whole time I felt kinda silly that I was this excited, but she just laughed at it and told me that she understood. We bought some general toilet articles, a few towels, some wine and, at her suggestion, a box of condoms, “just incase something ends up happening tonight,” she said. This only excited me more, of course, and I was getting a serious case of blue balls. We had talked about sex a lot on the phone, but I could have never imagined maybe getting a chance to experience it on my first night here. The only thing that worried me was that she had had sex with 5 other boyfriend’s in the past and being older and (obviously) much more experienced than me, I was worried I wouldn’t satisfy her. But then again, it wasn’t written in stone we were having sex tonight, so I was pretty sure it wasn’t gonna happen tonight anyway.
We took the bus back to the end of town I was staying in and after stopping for some pizza on the way back, we made it back to the apartment. We put some stuff away and almost as soon as we sat back down on my bed, we started to make out. As this happened, I gradually got more and more adventurous with my hands and started moving down towards her breasts and ass. After sensing that I wanted to touch them, she just went ahead and positioned my hands on them. The whole time, I was thinking that it was unreal to be lying here, making out with a girl and having your hands on her amazing, firm breasts and ass. At that point, she took her bra off and lifted up her shirt. WOW! Her breasts were beautiful. I started to suck on them lightly while I felt them up in my hands. She was whimpering a little and told me it felt good. While I was doing this, she started feeling down by the crotch of my pants and started rubbing my dick. I was rock hard. Then, all of a sudden, I felt her unzipping my pants and reaching inside the fly and hole in my boxers and had her touch it for the first time. It felt amazing. She pulled it out and started playing with it. Then, she moved down, pulled my pants off entirely and started to suck my dick. It felt really good. I was really nervous though and was having a hard time enjoying it and she sensed this, so she asked me after a few minutes if I wanted to have sex. Who was I to say no??
We got completely naked. I fingered her for a little while. It was the first time I had ever felt what a vagina felt like. Not what I expected (It wasn’t quite as overwhelmingly warm as I imagined, but it was most definitely wetter and slipperier than I had imagined). The inside of a vagina felt different than I imagined, but that didn’t make it any less amazing. I was in awe of the whole experience, that I was actually doing something like this with a girl who actually liked me and wasn’t being paid. After doing this for a little while, I grabbed a condom from the table beside the bed and we rolled it down my dick together. I got on top of her. This is when I started to experience some difficulty. I got really, really nervous and shaky and my erection started to soften. When I lowed myself down to her pussy and put my dick between her vulva lips, I tried a few times unsuccessfully to push it in. At first, I wasn’t hitting the right spot, but she took my dick by her hand and guided it down to her hole. As I tried to put it in, my dick started to bend and I could not get it in because I wasn’t hard enough. I tried my best to coax my dick into a harder erection, but I couldn’t. So, then she bent over and told me to put it in that way. This should be the best moment of my entire life here, I have a super cute girl BENT over, showing me her pussy, wanting me to do her doggie style and I only could maintain a half-boner. I always thought I’d be the type of guy who shot his load off in the first 30 s the first time, but it was the complete opposite. Luckily she was patient. She suggested we hold each other for awhile. I was shaking the whole time and she was saying “It’s okay, everything’s gonna be fine.”
I decided to go down on her. Before I did, she said “It’s ok, you don’t have to. I probably smell bad right now anyway, I was out all day long.” But I insisted. She smelled just fine. I couldn’t see anything, as we had the lights off, but I felt my way around with my tongue. More awe, more amazement on my part at what I was doing. I found her clit and started to lick away. I was still nervous and I was afraid she wouldn’t be receptive to what I was doing, but I felt her pelvis rock back and forth and she started to moan lightly, so I knew I was on the right track. She started to ride my face faster and faster and moan louder. As she was about to cum, she wrapped her thighs around my head and pushed my head into her clit harder with her hands. Then, she let up and fell back like a rag doll. Apparently, I was “amazing” for my first time eating pussy.
This eased the tension quite a bit and the fact that I got her off and heard her moan like that turned me on. I got back on top of her, put another condom on and repositioned myself. I fingered her for a to make sure she was wet enough and positioned my dick around where her hole was. After a bit of forcing, I managed to slide right inside her pussy. It (again) felt different than what I imagined, but it felt AMAZING just the same. The feeling you get when your dick makes the gradual slide into the pussy is unlike any other feeling on earth. That’s all I can really say. I had a moment of reflection here, as I was no longer a virgin. Then, I started to thrust slowly, in and out and then picked up the speed a little. It was really awkward. I was not used to this at all and the way you had to thrust when you’re on top wasn’t quite how I imagined it. Throughout though, she made comments about how well my dick fit and felt inside, saying “ooooh, you’re a perfect fit in here.†As I continued to speed up the pace, the whole bed starting shaking really awkwardly and loudly. I even slipped out a few times. The bed was on a really shitty box spring. My whole body was shaking and sweating a lot and the bed wasn’t giving me much help. So we had to stop and move the mattress onto the floor. Before we did, my girlfriend consoled me by holding me and continuing to tell me that everything was going to be OK and that I could take my time if I wanted to. Her experience was not thrown into my face. Instead, she was the sweetest possible person in the world about it.
We moved the mattress on the floor and when we got back on the mattress, I started to coax myself into a new erection. A minute or so later, I slipped another condom on to my dick and felt her pussy hole with my finger for wetness. She was ready. I guided it in this time with much greater ease. We were trying several different positions before I settled for Missionary. From that point on, I just banged away. She began to moan loudly as I continued my pace. After about 2-3 minutes or so and a couple of her orgasms later (I’m told), I finally feel that familiar feeling build up. I was about to cum. Then cum I did, as I exploded a full load into my condom, which when I pulled out, was RETARDEDLY FULL. Damn, that was good! She held me for a few s, and then stopped to admire the size of the deposit. We then held each other pretty well the rest of the night, looking at each other, admiring how good it was to be close to each other. I eventually fell asleep and felt great to have a girlfriend as caring and sensitive to an inexperienced guys needs, even though she already had a lot of experience herself. It might not have been perfect, but I couldn’t think of a more perfect person to lose my virginity to than someone as patient and helpful as her.
2377 Views |
Like
awkward first-timer
Processing your request, Please wait....
