Breaking In a Freshman Twink [m/m] X-post from /r/gaystoriesgonewild | 2016

Someone requested a story like this the other day so I gave them this one. I do think it deserves its own post though, so here it is.

It was my Junior year. There was this kid Shane who was a freshman that worked at the campus art supply store. Being a painter and frequent shopper there I developed a little crush on him, but every time I flirted or said anything suggestive he got really red and nervous. He was adorable. Really skinny twink type. He had messy auburn hair, green eyes and freckles. I had seen him around campus on the hotter days in tank tops and workout clothes and such and he had this just perfect body. Really toned, but not overly muscular. I tend to go for the androgynous type and he definitely had that going for him.

One day I thought of a way to at least get him alone, figuring there was no way he'd say yes to a straight up date request. I approached him on his cigarette break from the art store and chatted for a minute. I told him I was headed over to the art building to put in a request for a model for a painting series I was about to start. That part was true, but the lie I told was that my regular model backed out at the last second and I was desperate for a replacement. He commiserated and complained about some exam or something, and then I asked if he had ever done any modeling because he actually looked a lot like the model I was planning on using. He blushed of course and said no. I told him, no no, he'd be perfect, and that he should consider it, since he could get credits for it and I always made lunch for my models after they were done each day. After some more prodding he finally agreed to do it. We scheduled a date and time to start and agreed to see if it worked out before committing to a regular schedule.

So, Shane arrived as promised and I showed him around, kept it very professional. We walked into my studio and I told him I'd leave him alone for about twenty minutes just to let him familiarize himself with the place and find a comfortable position anywhere he wanted that he'd be able to hold for an extended period. When I came back in, he was stark naked reclining on a chez that I had draped in cloth and sat under a sunny window. I honestly had not been expecting this, and told him that I actually didn't require him to be nude, and he got embarrassed again. I reassured him that it was fine and that I admired his willingness to strip for me. And I began painting.

Over the course of a few weeks we became close friends, eating at least one meal a day together and painting three or four times a week. During one of our sessions I decided to make my move. I was positioning him for a painting and started messing with his hair. I started gently turning his head and when our eyes met I slowly leaned in and kissed Shane. He kissed me back. From there, knowing he had only ever been with girls, I took it really slow.

Eventually I introduced some stroking into our playtime. Then I went down on him about a week later. At that point we had a frank discussion about the things we were doing since he started to feel nervous that I was expecting him to reciprocate, and that while he was enjoying everything and was curious about doing more, he still like girls and wasn't sure if he was gay or what and was worried that doing more might "make" him gay. I told him that I would never try to guilt him or force him into anything he didn't want to do but if he ever did want to reciprocate it would be okay. I also let him know that what I didn't like terms like "gay" or "straight" and that my policy is just to like what you like and do what feels good. When Shane came back the next day he told me that he had thought about it and wanted to give me the same pleasure I had given him, but that he wanted me to teach him how to perform oral on a guy since he had never done it before. Funny side note, Shane eventually confided in me that he had bought various cock shaped fruits and veggies the day before to practice and "get used to" what it might feel like. So cute.

Well, now that the floodgates had opened and Shane was quickly becoming one of the best little cock suckers I had ever met, I became more sure that I was eventually going to be able to take this kids anal virginity. I introduced some light ass play during blowjobs and slowly increased the intensity of it until I was eventually fitting two or three fingers inside him on a regular basis.

During an especially passionate blowjob, Shane stopped just before I was about to finish (he loved the taste of cum btw, and insisted on swallowing it every time) and told me he wanted me to fuck his ass. I tried to hide my glee and calmly agreed. From there we got into the shower and washed each other, which to this day is one the most sensual experiences I've ever had. We fingered and poked and prodded each other, nearly cumming over and over again. But we resisted that urge until the moment of truth.

I laid Shane down on the same chez that I had first seen him naked on, which had pretty much been my fantasy from that very moment onward, and slowly stretched his asshole out with my fingers and some lube. I tried to make it as gentle an experience as I could, finally entering him with him on his side. I always felt this was the best position for communication and intimacy, which is important your first time getting fucked in the ass I think. Getting it from behind feels too anonymous, and legs over the shoulders prevents kissing while thrusting unless the bottom is some kind of gymnast. Those positions are great, don't get me wrong, just not for your first time IMO.

I didn't last very long unfortunately, considering how much foreplay we had done. Especially when Shane was alternating between moaning my name and god's and telling me with nearly every thrust to "fill him up" and that he wanted me to cum inside him. So fucking hot. So I announced my intentions to cum inside him and then did it. As I held onto his hips and blasted rope after rope of my jizz into his tight little bubble butt, Shane quivered and quaked and ejaculated all over the sheet that was covering the chez. It shot out of him like fireworks celebrating the creation of another college boy who lost his anal virginity to an experienced and maybe slightly predatory ;) upperclassman.

Not only did I end up with an amazing series of paintings that I'm still proud of to this day, but also an anything goes fuck buddy who I still keep in touch with years later.