Hi reddit, I’ve been a long time lurker of Gonewildstories and since I had a little extra time I thought I would post the story of my first time having sex. This happened a little less than 2 years ago and this is my first time posting anything like this so any comments/critiques are more than welcome. Grammar is not my strong suit so I’m apologizing right away if I miss anything after posting. I’ll also be separating the different sections so those who want to dive right in can.
Back Story/Intro
It's hard to really start at one specific place for my story so I'll introduce myself and the people involved so there won't be any confusion later on. The names of those involved have been changed and this is my alternate account so as not to attract the attentions of my friends who browse reddit. To describe myself I’d say I’m a rather average height standing at 6’0” tall and a rather husky fellow. The two involved with this sexcapade were my friend Matt (22) and his hook up buddy Andrea (27). Matt is shorter than average standing around 5’4” to 5’7” but otherwise a rather average guy with a little bit of muscle. Andrea was a little bit taller than him but average height. She was very skinny but not too skinny, with B cup tits and a decent ass. There's a little bit of backstory so keep that in mind if you have stuck with me thus far.
Most of the stories I have read around here involving threesomes were either planned or were spontaneous, this was somewhat planned a little over a week before anything happened. Matt and I were hanging out at our mutual friend's house around a bonfire pit talking about our plans for the fall. We were mostly talking about how Matt was going to start attending college for his associates while I was discussing my new career after graduating college with my bachelors. The conversation paused every few moments because Matt gets messages at minimum about once every 40 minutes. The reasons for this being that Matt talks to an assortment of women he seems to have as hookup buddies. It was after a particularly long silence Matt changed the conversation to a much different direction.
"I swear I could get Andrea to do anything I wanted to do, she’s always ready for me," he said this while talking to me and our mutual friend Max.
"Sure you can Matt," I said in disbelief and took it as him gloating about another girl he could sleep with at almost any time.
"I'm not lying to you Pornlovingphilosophr, I can get this girl to do whatever I want," he retorted to me. I looked over at Max and rolled my eyes. “I bet I could get her to do a four way with the three of us,” Matt said to Max and I.
At this point I was 23 years old and a virgin so I usually avoided trying to be too sarcastic when it involved one of my buddies describing their sex lives. I had become a bit fed up with his gloating as of then so I challenged him to hold up his statement, “I doubt you could ever make something like that happen.”
“I could get it to happen,” Matt retorted to me, “the only thing I couldn’t guarantee is if you two would even want to go along with it.” He had a valid point for Max since I couldn’t see him participating in any form of group sex, but for me it was different. I had missed out on several chances both in college and in my home town over the past few years so I had adopted the typical older virgin mentality of just wanting to get laid. Max had been well aware of me being a virgin since him and I went to the same college and we were roommates at one point.
Matt had no idea as I challenged his claim. “Prove it,” I told him. We spent the next few minutes talking about random things as we waited for him to send the message and for Andrea to text him back. Within 20 minutes of sending the message Matt received the answer he had expected and provided proof of her response to us, the only problem being that she didn’t feel up to it at that time since she was a bit under the weather. I was surprised at the response to the point of me bringing the idea up again later after several different conversations had transpired and several beers as well but nothing happened that night at Max’s house.
Fast forwarding a week later and I had just moved into my new apartment and was transitioning some pieces of furniture into the apartment when I saw my friend Matt pass by me and go up a dead end side street near me. He saw me wave and came over to say hi to me and shoot the shit for a little while. We talked for maybe 10 minutes before he asked me what I was doing that night. I told him I had today and tomorrow off and I was finishing moving stuff into my apartment during the day but tonight I wasn’t doing anything. From there Matt and I made plans to meet up later and to get Max in on whatever might be happening tonight.
The night kicked off with just the three of us having a few drinks and playing some card games with no real excitement in sight. At one point Matt almost got a group of girls to come hang out and have some drinks with us, but that was shot down because there were some underage girls present in the group. While Max was still present Matt asked me if Andrea could come over and realizing what he was proposing I agreed to let this girl come over to my apartment. After a few messages back and forth Andrea had told Matt she would come over within the hour. Maybe 20 minutes later Max left, probably knowing what was about to happen.
Matt and I were shooting the shit for about 20 more minutes when he got a text from Andrea letting him know she’d be over in 5 minutes. He told me to let him do all the talking beforehand about what he and I both knew was about to happen. I agreed since I didn’t want to have a chance at ruining my chances at getting laid. Andrea showed up and the three of us started to have a few drinks while Matt and Andrea were communicating by typing on their phones and then sliding them to one another. I had an idea of what was going on but I ignored it and continued to talk with them.
This happened a few times and Andrea left the room to go use the bathroom. I talked with Matt for a little bit and he asked me if I was really going to go through with this. “Pornlovingphilosophr no matter what tonight I’m going to fuck her, the only if right now is if you are going to too.”
Now most people are nervous before their first time but for some reason I wasn’t and I wasn’t feeling intimidated by doing it with someone else in the room. “Matt, I’m more than down; the only problem I see is that I’m a virgin and I don’t know if that’ll get in the way.”
“I’ll see what I can do but I don’t think that’ll be a problem,” Matt said to me. The rest of the conversations leading up to the event consisted of details, if everyone was clean, me being a virgin, and how to get it started. It all went pretty smoothly in retrospect, minus us getting it all started. At one point I suggested we play strip poker to get it started but Andrea said she was self-conscious about her body. What actually happened was all three of us stripped down to our underwear in my living room and ended up in my bedroom, lights off and the three of us preparing to do what we said we would in the living room. Before Matt and myself had gotten to my room he told me to “Not cum inside her,” which I hadn’t planned on having unprotected sex so I was ok with this condition.
The good part
When we got into my room I don’t remember who the first person who took off their underwear was but I do remember watching Andrea as she did. I quickly followed and went to my desk and grabbed a condom for myself and for Matt. Matt asked if I wanted to go first and as any eager virgin I was more than ready to go with my highly average 6 inches. Andrea looked at me and asked, “How do you want to do it? Since this is your first time.” I quickly answered doggie style and she got on my bed with her ass in the air. I put on the condom while Matt laid down at the head of the bed and Andrea had started to suck him off. I got behind her and was about to start fingering her a little but she stopped me telling me “I’m already really wet, go ahead and just fuck me.” I didn’t need to be told twice and grabbed a hold of my dick and lined myself up with her pussy.
I tried my best to hold off from just plunging into her right then and there and tried to rub my dick up and down her slit but I had a hard time finding the right place. I continued this for a little bit and then managed to get it in. Looking back on the experience I knew it wasn’t the best pussy I’ve ever had but at that moment I was in heaven as I slowly pushed into her. I was really surprised by the heat of her pussy, up until this point I knew it was going to be warm but I hadn’t expected at how warm it was and how wet she was. I got balls deep and savored the feeling for a moment. Meanwhile Andrea moaned a little bit as I got balls deep into her. I then grabbed her hips and started to move. Despite what I was experiencing before I was in heaven right then. She wasn’t the tightest looking back (that could be expected from a woman who had 2 children back at her home), but I could feel her pussy gripping me as I pulled out and pushed back in. I was savoring the feeling and I continued to push in and out of her a little awkwardly (I slipped out a few times and she had to help me get back in) but I managed to actually build up a semi decent rhythm. Andrea must have been enjoying this because I could hear her moaning on Matt’s cock while I slowly built up speed. I continued to pound into her and more of her moans were being muffled by Matt’s cock in her mouth but as a virgin I was starting to get close. My thrust became more erratic as I chased after my orgasm and she continued to moan, but unfortunately (despite trying to avoid coming) I came a bit earlier than I wanted to and buried myself balls deep into her.
After coming I hadn’t lost any of my hardon and continued moving after coming into the condom. I must have continued this for a few minutes before I slipped out (still hard) and started to finger her from behind. She must have enjoyed it because she had taken Matt’s dick out of her mouth and started to moan more as I started to rapidly finger her from behind. Matt must have realized I had cum and asked if I had indeed done so. I told him I had but I was more than able to still go, but he stopped me and said that he wanted a turn so I took off the condom and disposed of it while he got behind her and started to fuck her from behind like I had only facing towards me at the end of the bed. I kind of stood there a bit awkwardly for a second before she asked me if I wanted my dick sucked so I stood to the side of my bed while she started to suck me off. Now I had just cum a few moments earlier but compared to her pussy this blow job was a bit lack luster, don’t get me wrong it was a good first blowjob but it was nothing compared to her pussy. She continued to suck on my dick moving from taking most of it to just sucking on the head and I was enjoying every second of it. Somewhere in here is where me and Matt actually high-fived over this girl while he fucked her and I got sucked off (Eiffel tower knocked off my list of things to do now). He continued to pound into her to such an extent that she was getting sloppy with her blowjob and had to take me out of her mouth completely and seemed to be enjoying what he was doing.
The next part of the threesome is a bit blurry to me given that it had occurred almost 2 years ago, but I eventually got to get a second go at Andrea after Matt had managed to literally fuck her (on her back) across my bed to where she was almost on the floor. At this point I had taken a seat (my bed at the time was a single so there wasn’t enough room for me to hang out with them) and was masturbating while waiting my turn. We had a laugh and Matt asked me if I wanted another go. Even if I hadn’t been masturbating the entire time I was waiting, I knew I’d still be hard and ready for round 2 (something that has carried into my other sexual experiences). I got up, grabbed another condom while Andrea laid on her back waiting for me. Neither of us said anything as I grabbed my cock and again lined myself up with her pussy and pushed in slowly again.
I started off slowly thrusting in this position but I quickly gained speed as I thrusted faster into her. It was surreal feeling at the time and I could tell I wouldn’t be coming anytime soon so I put a lot of my effort into just trying to keep a good rhythm going. Andrea had been moaning the entire time and eventually asked me to go harder. I pulled out as far as I could and pushed as far into her as I could (again I slipped out once or twice but I was able to get back in relatively easy). She really liked this but I was quickly getting tired. I don’t know if it was all the porn I had been watching but for some reason I leaned back, grabbed her legs, and started thrusting into her while sitting up (my favorite thing to do in missionary to this day). I tried to play with her clit a little while in this position but my lack of experience led to me just focusing on trying to keep a good rhythm. This continued for a while until I had her climb on top of me (I was getting a bit tired).
To be continued…
Source: reddit.com/r/gonewildstories/comments/3ef52v/my_first_tim_was_a_threesome