Where it happened: A hotel
Langauge: english
Sex: Female
Rating: 5
Category: Straight
I’ve been working at my work for about 10 months now. The first day i started working, i noticed the bartender. He was so cute. Not hot, because he didn’t have this great body or anything, but he was cute. And once i started working there more often i got to know his personality, which was even better than his looks. He was the very flirty, confident type of guy. I would always look forward to the weekends at work, because that would be when he was bartending. We just started flirting the entire time we worked, and then i started to fall for him. I didn’t want to just because i work with him, and because he was a lot older than me, 15 years older than me. but i fell for him anyway. I couldn’t stop thinking about him. And then people started to notice that we always talked and flirted together and they saw the look in my eyes when i was around him, at least that’s what they tell me they saw, i can’t really see my own eyes. So i started talking about having a crush on him to one of his closer friends. I made a comment that said something like I like him, but i have no chance because he doesn’t like me. And his friend informed me that i was highly mistaken, and he likes me aswell. So, when we both found out we liked each other, our flirting and our conversations became serious, not just kidding around anymore. We stared talking about hooking up outside of work, but because of the age difference, we couldn’t have a relationship because work would fire us both and my dad would kill us both. So we decided it would just have to be a sex thing if we really wanted each other that bad.
We arranged to leave work and go to a hotel the weekend before Valentine’s day weekend, 2003, but i called him and told him i changed my mind because i wasn’t ready to lose my virginity yet, he said that i was ready, i was just scared, which was true. so, for the next week, he kept calling me chicken little, which pissed me off. So i called him and said we could go the following friday, which was coincidently, Valentine’s day. Trust me, it wasn’t my intention, nor his, to make the date be on valentine’s day, we both hate the day.
So, valentine’s day rolls around, the restaurant is slammed, the bar is packed, and we are supposed to close at 11pm, we didn’t clock off until 12:45AM that night, i was SOOOO tired because i’d worked for almost nine hours constantly moving, sitting down only once or twice all night. so he comes up to me at the end of the night and says, “the story is i’m giving you a ride home because you’re dad’s busy and can’t come pick you up” i was like, OK, so, i slipped out the door and started to walk to his truck with my stuff and he came about a minute later. I was pretty much sleeping while we were driving around because i was so tired and i kept yawning. We had to drive to three different hotels before we found one that had a room just because it was valentine’s day.
he went inside and paid for this room while i was sitting in the truck thinking “oh my god what am i doing, why am i doing this? I can’t believe i’m doing this.”
so, we go in this room and i sit on the left bed and he sits on the right and i’m just watching tv, while he says he’s going to go shower. He showers and i put on my pj pants and my tank top. he comes out of the bathroom in his sugar daddy candy bar pj pants that i gave him for x-mas as a joke. I never thought he’d wear them, but he wore them for me.
we sat on separate beds for a long time before he asked me if i had lotion so he could give me a backrub. God, he must have been a masseur in a previous life or something because i was in heaven for those thirty minutes. he then discovered that i was ticklish. he entertained himself watching me jump and squirm to try and stop him from tickling me. one time i jumped and he grabbed my hips, picked me up and set me on his hips while straddling him. Then it got weird, and i was like, OOOkkk so, this is weird. He goes, you don’t have to do anything if you don’t want to. After that i just got off of him and we just held each other for hours, and then went to sleep.
He never really slept, he fidgets all the time. i was pretty much asleep, but he had his hand on my inner thigh and i knew he was there, cuz i could feel him stroking my thigh and going back and forth, and then getting lower, and then higher, and then he moved his hand over and started to finger me, and i let him, just because it felt right, and it wasn’t weird anymore. He asked me if i wanted him to stop and i said no. he asked me again later and i said only if he wanted to, and he took my hand and put it on his cock and said, does it feel like i want to? I was like, NO, he was hard as a fucking rock.
At this point we both still had our clothes on. He climbed over and got on top of me and just started to kiss me and move his hands all over me.
After a while he asked me “Are you sure?” i said, yeah, if you’ve got a condom on you. He said yeah. he went and got one and came back and we just started kissing again, then he goes “You’re a 100% positive?” I just pulled him towards me and kissed him hard and said uh huh.we took off each others clothes and were kissing some more, then he inserted, and i was waiting for the pain, but it never came, I was so scared about how bad it would hurt to lose my virginity and it didn’t even hurt. He started out slow just because he thought it would hurt and then we started going faster and trying different positions and stuff. He was always on top doing all the work just because i had no clue what the fuck i was doing just cuz it was my first time. God he was good though. We were going at it for about 45 minutes.
after that, we just held each other and fell asleep in each others arms. about 2 hours later we did it again, but it was a spur of the moment, caught up in the passion kind of thing, so he didn’t have a condom that time, but he pulled out.
I’m totally in love with him now, and i know i’ll never forget him. Hopefully we’re going to make this a regular thing, and maybe when i’m 18 and my dad’s out of the way, we can have a relationship and be together.
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