I was 19 and had been working an office job for a month now. It was boring, but the girls were nice to look at and lunch was always free. One of the center directors was always happy to see me, Dan was 38, taller than me and built like a male model ( he had been a cross country all-star in college ). I just assumed he wanted to be friends, but now i was wondering as our daily interactions were turning into flirting sessions. He started by telling me i was "too cute and sexy for the boys at school, ". He had started inviting me out, but i would politeley shrug off his comments, unsure of how to react. (I had 1 gay lover a couple of summers before, it was fun but nothing special; but I wasn't looking for another, especially at work for everyone to find out.) It was rumored dan was gay, but no one knew for sure. I knew he was, when he told me one day he " had a sexy feeling about me, he knew he could treat me great and we would have hottest times together, he just knew i would love it". I didn't know what to say so I made a stupid excuse to leave. I avoided him for a day, but thursday i had to set up his new computer. I was under his desk, on all fours plugging in wires while he sat on his couch watching. I heard him comment on my butt and legs, (i wore shorts to work and have very little body hair so my legs look smooth and girlie when i'm tan in the summer) and it reminded me of how my body turned the first guy on; i wiggled my butt at the memory then cursed myself because i knew dan was watching. He was and before i left his office he had talked me into riding with him to the company picnic that saturday, we lived in the same neighborhood. I did it mostly because his boner had popped a tent in his pants and i was embarassed to be in his office while he was hard i could just feel the rumors starting. Saturday morning i was ready and dan picked me up and we went to the waterpark our picnic was being held at. We did not talk much during the party, i mostly hung out with the younger workers but a couple times he found me, gave me a drink and made it a point to check me out and try flirting, i felt like a piece of meat standing half-naked getting hit on by this guy, but i started to feel sexy too. The day went on and pretty soon it was time to leave, dan and i started our drive home. We took a couple of vodka shots then dan started tickling me, giggling as the liquor buzzed in our bodies, he asked me if i wanted to come back to his place, at first i said no, but we pulled into his garage a few miuntes later anyway, some excuse about needing to run in just real quick. A few minutes later he came into the garage with drink, a cosmopolitan he called them and convinced me to come inside. I was in his living room looking at photos on the wall feeling great from the drink, and i wandered around the house. I guess i was asking for it, half-naked in just my swimtrunks and flip-flops; a few of my girlfriends have told i was asking for it, i just didn't know it. When i got to a tv room dan was there slipping a cock ring around his dick. I was stunned as i realized i was looking him up and down and he was better built than my first boyfriend, it was turning him on to look at me and he told me so, then he offered me a cock ring. "Just try it" he said as i looked at his dick, it was sexy, he was smooth and very defined, i wanted to follow the v down to it (he would later tell me that it was almost 9", almost as thick as the red bull can he used to make our drinks). My body must have remembered how it had cum with the first guy because i started to get horny and remembering how to play with a top. I felt his hand squeeze my butt and he nibbled my neck, then told me i was "too sexy it was going to take all night to fuck me gay for him but he could do it and we would love it!" then he told me he "knew i'd had a boyfriend before, but how many?" i said 1 and that made him happy, "he loved new twinks". Before my shorts came off i made him promise that no one would ever find out and i laid on the couch so he could put the cock ring on. I hadn't been wanting to do this since the first guy, but he was making me feel so sexy and wanted me so much, he told me " you're gonna love my dick, try touching it cutie". i moved my body closer to his, we were in a 69 position as he put the ring on me and tried to remember what i did for the first guy. i didn't touch his cock so much, i licked and sucked it alot, so that's what i did here. "OOOohhhh yes cori that's great !! i think it surprised him as i kissed the head of his cock then ran my down the underside as i slipped it into my mouth. i did like giving blowjobs as i quickly remembered, trying to get as much of it on my lips as possible, i wasn't even feeling his hands on me as i sucked his cock into my mouth, it was a very sexy cock and i was surprised at my own need for it as i deep throated him, somehow remembering to breathe through my nose, buried in his stomach right above that sexy dick. dan was picking up the idea that i knew what i was doing and asked me "you had sex too - how often did your first boyfriend and you have sex?" "i certainly knew what i was doing with my mouth and he could tell now that i did want it and he would take all night and i would love it" i told him all summer long, not realizing at first that i'd just confirmed his thought that i was the bottom he thought i'd be. that's when it happened, the first of 5 or maybe 6 times that night. he started kissing my hole, and eating me out, it felt wonderful, that never happened before. i moaned and pushed against his mouth, he slapped my butt playfully and told me get on my stomach on the couch "you're sweet butt is driving me crazy, i want it " and i did just that on all fours. "i saw you wiggle your butt at me in the office the other day, you gave me a hard-on you sexy little boy-toy; you were asking for it, did you do that on purpose? i replied "no, i didn't even know you were watching me" caressing my butt cheeks slid up behind me, standing in front of the couch and hugged me, nibbling on my neck "well you were asking for it, your sweet butt was and now we're gonna have fun , i'm gonna give that sexy boy butt more than it needs". i think i blushed hoping he was wrong. he stepped away suddenly and i followed him to the bar, we did another shot and he grabbed a tube of some famous brand of lube. he led me to a bedroom and i was on all fours near the edge as he stepped behind me, i could feel his stiff dick poking a butt cheek, he told me again how sexy my sweet butt was, he was so happy he would make sure i loved it. he moved us further down the bed, in front of a mirror on the wall "this is one of my favorite parts cori, when we start i want you to look at me behind you, don't stop looking at me i want to see your pretty face as i fuck my new boytoy "ok " i replied a little too quickly for my comfort, i still had some reservations about this "if you stop looking at me i'll make you walk home right now". the lube was cold, then warm and i was nervous as he slid his cock up and down against my hole, he leaned forward, nibbled on my neck and i just kept looking at his eyes. his cock slowly pushed into me, watching me intently for my reaction as it slid in inch by inch. he stopped "how does that feel cori?" it was a good sized cock and surprisingly didn't hurt at all, it felt good, but i was not ready to admit it yet. "yes, it's fine", he clutched my hips and pushed further "i'm almost all the way in sweetie, how does it feel? he slapped my butt playfully and pulled out to the head. " it feels ok, you can keep going dan" he smiled and started pushing into me again slowly, he was almost all the way in when i moaned out "yyeeeesssss" just as his hips smushed into my butt cheeks. he giggled in delight and knibbled me ears and neck as he started to screw me from behind, all the while watching my eyes roll back and forth and my lips form a huge grin in the mirror. he was much bigger than my first boyfriend and it began to feel amazing i was very soon bucking back against him in rhythm and we were doing just like he said we would "lovin' it !!" i between telling me how sexy i was, how much he like my sweet butt and how good a twink i was being he would spank me a little or pull my head back by the hair and say it into my ear. at a couple of points i had to bury my face into a pillow and i couldn't touch myself for fear of coming. i was starting to realize now i had a new boyfriend, i still wasn't sure i wanted this. "do you like this cori?" he said after stopping and holding us still for a moment "most boys playy with their cocks while this happens..." "i will cum fast" i replied hesitantly. "you really are enjoying this, was it this good with your first man? i didn't want to but i said yes and he giggled proudlymoving my hips forward and resuming our doggy style sex session. "go ahead and cum sweetie, you'll enjoy it, and you'll be cumming alot tonight on my cock like this!" my butt did that wiggle thing again which he noticed and spanked me again as i grabbed my cock. minutes later as he slammed his cock into my sweet spot i shot my cum all over the bed, with him nibbling my neck and whispering about my sweet ass in my ear.
*the names and locations have been changed*