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My Fantastic Freshman Experience

(Names changed for privacy)


So let me start this off by saying I’m bi, I have an underwear fetish, and that going into college I had never had sex.

Ok so backstory: No one I knew from highschool was going to go to the same college as me so I had to go with a random roommate based on a personality quiz. Luckily I got a guy (Josh) that seemed pretty cool.

The day after move in, Josh invited me to meet and hang out with two his friends from highschool (Will and Trevor) that were roommates down the hall.

When we walked in, there were two things I noticed, they were both in just their underwear and that Trevor was the sexiest guy I had ever met. It wasn’t that he was really fit or anything like that. I just knew I was in love.

So Josh also noticed that they were in just underwear and commented on it. Will said that it was the most comfortable way to hang out (I couldn’t disagree) and Trevor invited us both to take off our pants. I paused but Josh immediately dropped his pants and so I followed suit.

Now seeing as I have an underwear fetish, I feel the need to include everyone’s style(s) of choice seeing as I got to see them all in their underwear alot. (Luckily I was able to control my boners)

–Me: boxers, briefs, and boxerbriefs from Hanes, American Eagle, and alot of various other random brands.

–Josh: Boxers and boxerbriefs. (American Eagle and Hanes)

–Will: Hanes Boxerbriefs

–Trevor: Hollister, Stafford, and Hanes, boxers and tighty whitey briefs

Finding out about Trevor wearing briefs came from me wearing briefs a few days that we hung out and him finally deciding to where them one day when we were hanging out.


Over the next few weeks I hung out with them alot (always in our underwear) and we ended up finding out that Trevor and I were into the same type of activities and we’re in the same major. Because of this, Trevor and I ended up spending alot of time together studying and doing homework.


So now that I have introduced you to Trevor, Will, and Josh. Time to tell you about the other main part of my social life.

I joined a few clubs on campus and through one of them I meet a girl named Ali who I quickly found out was bi and I told her I was too. We hung out alot and quickly became best friends. She ended up asking me if I wanted to have sex after the conversation of sexual experiences came up. The two of us talked about everything. Especially our interests in people and who we found hot/would sleep with along with us having sex quite a few times. (We were just friends with benefits though but we did have planned to try to find someone to have a three-way with)


So now that you know about that part of the story, back to the group of guys.


One afternoon we were started talking about girls, relationships, and sex.

Trevor had never done anything (even date a girl), Will had dated girls, made out, and gotten blowjobs, Josh had multiple girlfriends and had sex with all of them. Josh also even admitted to experimenting with one guy in highschool. (Apparently neither Will nor Trevor had known about it).


He then asked us if any of us had ever experimented. I decided to go ahead and tell them i was bi and that as said at the beginning, I had never had actual sex but I had dated a girl and a guy in highschool, made out, and had oral sex with both of them.

So the next day Trevor and I meet up to work on a project for one of our classes. When I got there he was in just his tighty whities (this was the first time he wore them). As I dropped my pants he saw I was also wearing briefs and then told me he could see the outline of my cock through them. I jokingly said thanks and asked if he liked to see it. To my surprise he said yes. I was somewhat caught off guard and started to wonder how they found out I liked Trevor and decided to make fun of me by teasing me. When I came to I simply ignored him and sat done to get out my laptop to start work.

He sat down next to me, took my laptop off of my lap, pushed me back on the couch so that I was laying down, then started to make out with me.

We made out for a few minutes before I realized what was happening and pushed him off of me asking him “What the fuck? How did you guys find out I like you?”. He responded that he didnt know I liked him but was glad that I liked him but he had liked me since he first met me and he wanted to go out with me. Accepting that it could be a trick and decided that it would be worth doing out with him even if it was a trick.

So the next day (which was a Friday) he and I went to dinner then back to his room. (He told me that he had asked Will for the room in case his date went well since Josh and Will didn’t know we were going on a date or that he wasn’t straight). We quickly removed our pants and shirts and started to make out. We both started to give eachother handjobs which quickly lead to him pulling my boxers off and giving me a blowjob. At this point I knew that this definitely wasn’t a joke that they were pulling on me. He quickly started to deapthroat me which is pretty impressive since it was his first time and I’m about 7.5 inches long. After a few minutes, I pushed him off of me and then gave him a blowjob (he is about 6 inches).

He asked if he could come in my mouth and I gave him a thumbs up. After he came he got up and got a condom out of his desk drawer and told me that he wanted me to fuck him and take his virginity. So I pulled on the condom and ate out his ass some to get him lubed up. Then I slowly started to push my cock into him. Slowly at first to let him get used to it, but once I was fully inside of him he told me to start fucking him as hard as I could. I gladly did and he started moaning very loudly which I’m sure let everyone on the hall know what was happening. After a few minutes I came and we then payed in eachother’s arms. Then we started talking and he told me that he was also bi but had always been afraid of his friends not accepting him. But that when I came out as bi and they were cool that he knew he could too. He told me that he wanted to tell them the next day at lunch. We decided that when we all met up one of us would walk up to the other day hey and have a quick kiss then tell them that he is also bi and that we are now dating. Of course as soon as I got the chance, I texted Ali and told her the news. I also told Trevor about the situation with Ali and he said he was ok with it because he knew that he couldn’t give me everything a female could under two conditions:

1. That she is the only person

2. That I talk to her about him joining the fun.

I was so excited and immediately told him that wouldn’t be a problem because Ali and I had already wanted to find a third person for three-way and such. So the next day at lunch we told Josh and Will about everything and then we went to Ali’s room to let them meet. After I introduced them we talked about how this relationship was going to work and decided that Trevor and I were dating in an open-to-Ali relationship where any of us could have sex with eachother. We then decided celebrate by having our first three-way.

But that is another story.

Let me know if you want to know more


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