Where it happened: Hotel
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Alright. And so. December 17, 1996 (I’m super weird about remembering dates), I was in my basement working on multiple end of the semester projects. It was my senior year, I was 10 days away from turning 18. I took a break & went into a “Teen Chat” room and met this girl Julie that lived probably an hour and a half drive north of where I lived. She was a 17 year old junior in high school. We hit it off quite well and after a few weeks we were all “I think I love you…”. But I won’t get into that too much. Ok so we talk about getting together on New Years Eve and she says something along the lines of, “We’d have to get a hotel room or something…” Which I kind of thought was odd. I mean we hadn’t talked about hooking up physically at all, so that kinda came out of left field. I think she was in a pretty horny situation though, cuz she had just recently broken up with a guy she was having regular sex with. It was her first…they didn’t have sex until they had been dating for six months. But anyway…we finally actually made plans for me to drive up there & spend the night in a hotel room together. I don’t think we ever officially said we were going to have sex, but I’m sure it was at least implied. I was a complete virgin at this point…had never even kissed a girl other than playing spin the bottle in 5th grade. Okay so Friday, January 17th, I drove up there. I’m gonna make this pretty detailed just for the hell of it. All day I was super nervous and afraid that I wouldn’t even be able to get a boner. I think I played around with it a little myself and could barely get hard. I also looked at porn mags before I went up there, just to make sure I knew exactly what was going on with a vagina. How funny is that? I stopped at a gas station on my way up, and got like a soda, and planned to get a box of condoms as well…but in the end I like, chickened out. I was so shy that buying condoms would have been way too hard for me. Which is so absolutely ridiculous when you think about. Having protected sex was less important than being a lil embarrassed in front of some gas station worker that I would never see again?? Whatever. Alright my journey was a bad one cuz it took me forever to find her. She was at a house where her friend was babysitting. But I didn’t have very good directions…and I guess I was pretty stupid about finding her. Eventually, I call her house at maybe 10:30 at night from a gas station pay phone (after leaving mine at maybe 7) and her 14 year old sister answers. Which was lucky…night could have been completely dif if it wasn’t for her. She played an answering machine message from Julie that had the telephone number where she was hanging out with her friend. (She told her parents she was sleeping at her friends house of course.) I got the number where she was staying, got directions & finally got to her friends babysittin house at like 11. I got out and she came running out and hugged me, I gave her some roses that I bought on the way up. She was…ok looking. I had never even seen her picture before. Can you imagine that? In this day of digital pics, the idea of meeting someone offline without even seeing their pic seems crazy. She didn’t know what I looked like, either (other than describing ourselves, obviously). She was like 5’4 skinny, pale, dark hair & eyes, small boobs. So I went in this house with her blonde friend Chelsea (there was talk of a threesome with me, Julie, and this Chelsea weeks later online, but nothing ever came of it 🙁 ) and some random little kids. So…we just awkwardly sat on her couch for a while, me not saying much. We kissed a little but her friend & the kids were around. We got cuddly and I started getting hard, so I wasn’t worried about that any more, haha. Eventually the parents of these kids came home, and Julie and I followed Chelsea back to her house for some reason. We got there and Chelsea and Julie have this huge conversation in her garage, that they eventually bring me into. Apparently, Chelsea wasn’t too thrilled about her friend spending the night in a hotel room with some random guy that she met online. She offered for us to come inside and just talk and hang out in her basement or some shit, but we were like “Well, no….”. Finally Chelsea let’s us go to the hotel under the condition that Julie will call to tell her she’s alright at 7am the next morning. We get to the hotel, rent a room with two beds cuz they were out of rooms with one. We order a wake up call. I’m sittin on one bed, she’s sittin on the other. Okay, here’s the juicy stuff you were waitin for. I also have to mention how shy I was around her…barely said anything. It’s kind of weird she let me bang her (especially considering no condom).
I go “So…”
She goes “So….” And we kind of laugh. She adds, “This is kinda awkward.”
She comes and sits next to me and I put my arms around her. We kind of hug. Then kiss. I stop and say “I don’t…have anything.”
“Me neither,” she says. And continues “It’s probably not a good idea anyway. We just met.”
So I’m a little disappointed here…I mean we talked about probably doin it before I came up, so what had changed now? My shyness I guess. I probably didn’t want to have unprotected sex at this point anyway, and didn’t think she’d let me. So I was thinking maybe blow job, and maybe explore a naked female a bit for the first time.
We kept kissing in this sitting upright position and I tried to pull her back, laying on top of me. She resisted the first time I tried, but let me the second. After a bit I rolled her over and laid on top of her. I started pushing my erect dick up against her leg, trying to turn her on and let her know I was hard. At this point in my life, I really didn’t know I had a huge dick. No one had ever seen it (erect, at least, and it’s usually pretty small when it’s flaccid). I had seen porn, but of course those are usually pretty big. I had measured, and knew it was seven inches. I thought the average was about 6 inches…so I thought I was maybe a little bigger than average. And I had no idea how my thickness ranked.
Oh and here’s how we were dressed, just so you have all the details. Me- some red button down flannel, a long sleeved white cross country t shirt underneath, jeans, boxers, socks.
Her- a white sweater, white undershit underneath, white bra and panties (I would find out soon), jeans.
Ok so I guess pushing my fatty up against her thigh turned her on pretty good. She got up and pulled the sheets back off the bed for us to get in. Then she got up and turned the lights off. She came back into bed and took her sweater off, then started unbuttoning my flannel. I took over and took it off as well as the t shirt underneath. She ran her hand across my chest and stomach. Said “You’re so skinny! I love it…” (she had mentioned before that she was attracted to skinny guys). Ok, so what happened next…it was eleven years ago…but, I’m pretty sure I got on her again and she took her white t shirt off, then her pants so she was just in bra and panties. Then took off my pants (horny girl!) and giggled a lil and said “boxers..”. She startled me and I sat up to kiss her some more and she said, “I want to make love to you, Jeff.” I responded “We shouldn’t…” and she said “I know, it’s hard.”
Ok so, what happened next? I think I ended up on top of her and started feeling her tits thru her bra. She said, “Here,” and unclamped her bra in the front. I moved the cups aside and she said, “Have you ever seen a girl naked before, Jeff?”
“No.” (I think she really got off on the whole virgin thing.) I felt them then sucked them, in turn. She remained silent. I moved my hand down to her crotch and started rubbing her damp panties. She said “Oh…that feels good….” So soon enough I put my hand in her panties. My finger found its way into her pussy and I started fingering her with one finger. She started moaning a lot, roatiting between “oh”, “ooo”, and “ah”. I added a second finger and went faster and faster til I finally stopped. (By the way she had a very hard time cumming in general, I think she had only had an orgasm twice in her life at this poing, once during sex and once by herself.) She asked, “Have you ever done that before?” which seems like a pretty stupid question considering I just told her I had never seen a girl naked. So I told her no. She took off her panties and slid her hand slowly down my chest, finally reaching into my boxers. She gasped. “You’re HUGE!” Slid my boxers down so it was out, and started stroking. “You’re like twice the size of my last boyfriend! So thick…”
Soon enough, I was pretty anxious for head, so I said “Ssss…..suck..it.” She sat up and pulled her hair back.
“Have you ever had that before?” she asked.
“No.” So she started sucking for a little, I said “Faster” at one point (Hmm…kind of coming across as an ordering around pricky) and she started going faster but then stopped, and came back up next to me. She put her hand back down there but kind of hit my nuts, and I wasn’t used to having someone’s hand down there, so I kind of pulled back quickly.
“What?” she asked.
“Nothing.”
“What is it?”
“Nothing.”
“There’s a naked girl next to you, Jeff. No parents around. Unless it’s me…”
“It’s not you, you’re beautiful.”
“Thanks.” Then I think she said, “Let’s put this away, just in case…” and pulled my boxers back over my big hard cock. So we laid there for a little, I didn’t really think she wanted to have sex (although looking back now and reading this, obviously she did) cuz I mean she’s the girl. She’s the one that could get preggie, I was surprised she wanted to. Anyway, she eventually looks up at me and I start kissing her and get on top of her. She grabs my dick and points it at her pussy, still in the boxers though. I started pushing against her entry & finally decided to maybe start putting it in, or maybe put it in once to see…how she would react, or whatever. So I pull my boxers down and start to push in where I think I should, but I guess I was a little high, cuz I got some resistance. So I pulled back and started over, found my way in. When I had fantasized about sex before, I always imagined putting a little bit in at a time. So that’s how I did it. Maybe a little more than the head, then a pause..half of the cock, pause…3 quarters of it so I was basically lying on top of her normally, pause….then thrust the whole thing as far as I could, which made her flinch back as though she was in a lil bit of pain. So I pulled out a little and gave her one of those deep hard thrusts again cuz it felt so good, and she winched again. I said “Sorry,” and she replied “No! It’s just…I’ve never had one in me that far before.”
So I started up a little rhythm without putting it all the way in cuz it really seemed like it hurt….oh how I would have done that differently now..I’m sure it was a “good” kind of pain. Anyway she started again with her “oh…ah…ooo….oh…ah…oh…” I gave it to her a little harder and faster, making her moans louder, then went back to original rhythm. She started moving her body with me, thrusting her hips up and down with my cock…I loved that. At one point-
“Oh God…oh Julie…”
“You’re not about to cum or anything, are you?”
“No.”
“Good, pull out before you do. I don’t need to be getting pregnant.”
Anyway, towards the end I put my hand down there, getting ready to pull out. I gave her some more hard thrusts, and that, combined with how slimy my dick felt sliding in and out of her, put me over the top. I started having an orgasm so I pulled out…and very idiotically kind of came on her pussy anyway. She said “Oh my God” and ran off to the bathroom to clean it off. So there’s the sex. We saw each other a few more times but then she kind of switched to some other guy she met online cuz she “loved him more” even though she was telling me she loved me and having sex with me…yeah, that was a nice first experience with a girl for me. Whateva. The end.
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