My friend gets me to take a guy’s virginity [FM]

During my mid-20s, I lived on the island of Guam for a little more than a year. While there was a lot to enjoy about my time there, one of the biggest life changes I found there was how easy it was to hookup. I used to have a new partner every few months or so, but in Guam, I was fucking a new guy ever other week or so. This is one of those times.

On a Friday night, my friend Liz texted me to meet her out at a bar with some guys. I get a taxi to the bar (Mac & Marti’s, for those who have been there) and meet her and the two guys she was with, Steve and Dan. They were both military guys who were on the island for a bit, and she had been hooking up with Steve for a few weeks. I start chatting with Dan; he was a little goofy and seemed a socially awkward, but funny and nice. He was maybe a little under 6 feet and not in great shape, but not fat either. We chat for a bit over a couple rounds of drinks.

At one point, Liz and I went to the bathroom, and she asked me what I think about Dan. I said he seemed nice, and asked why she was wondering. She told me that Steve wanted to get Dan out of his shell on this trip. Steve told her that he’s pretty sure that Dan is a virgin, and joked (or not joked) that he was hoping to get Dan laid while they were in Guam. I think Liz was hoping that maybe we’d hit it off.

I was pretty turned on by the thought of taking Dan’s virginity; the only other time I had done that was the summer before freshman year of college when my ex-boyfriend and I swapped virginities. I gave it some thought as we walked back out, and I started being a little more flirty towards Dan. Another round or two later, I figured why not, and suggested to Dan that we get out of the bar. He seemed kind of surprised by this, but said sure. We tell Liz and Steve that we’re leaving, and she laughs and said to have fun.

We got outside the bar, and he asked me where I want to go. I suggest we go to his hotel room, and he nods. He starts walking, and I come up next to him and grab his hand. He looks at me, and I lean up in kiss him. He seemed content to leave it as a quick peck, so I made sure to hold him and make out for a few seconds. His hotel was maybe a 10 minute walk away, and he is quiet for the whole time.

We to the hotel and go up to his room, and start making out by the door. He was not the best kisser and used a lot of tongue. I expected him to make a move towards the bed, but he was in no hurry, so I walked over to the bed, took my dress off, and lay down. I’m about 5’3″ and 135 lbs or so, with C-cups and some curves. He comes over to the bed and we start making out again, but he stays completely clothed. I take his hand and put it on one of my boobs, and he reaches under my bra and begins stroking my nipple. I reach down towards his shorts, and begin rubbing his hard cock through them. He starts moaning softly as I keep rubbing it.

I unzip his fly, and he stops me to say he needs to tell me something. I figure I know what he’s about to tell me, and listen to him tell me that he’s never done this before; the furthest that he had gone before was making out. I reassure him that it’s really okay, and ask him if he wants me to keep going. He says yes, and I reach down again to pull down his shorts and pull his cock out. It was pretty good sized and fully hard. I stand up and get fully naked, and he takes his clothes off too. I get back on the bed and take his hard cock in my mouth. He closes his eyes and moans again.

I don’t want him to cum just yet, so I stop after 30 seconds or so and ask if he wants to have sex. He says yes, but then says he doesn’t have a condom. I had some in my purse, but I decided I would let him go in bare. I know it’s a little risky, as he could have been lying about being a virgin, but I was horny and wanted to make sure this was good for him. He seems really concerned about not using a condom, but I reassure him that I’m on birth control, but tell him that I can grab one if he’d prefer. He said he didn’t need one, and I asked him how he wanted to do this. He was really nervous and didn’t know what he wanted, so I suggested missionary.

I lay back on his bed, and he got on top of me. The tip of his cock was at my pussy, but I think he expected it to go in more easily than it did. He fumbles around for a few seconds, and I reach down to pull his cock into me. He paused for a second, like he was still in shock about what was happening. He started fucking me slowly. It felt like he wasn’t going that deep into me, so I used my legs to pull him deeper, and he got the hint. This continued for a bit; I wanted to reach down and rub my clit, but he was laying directly on top of me and I wanted to make this about him.

Dan started to breath heavily and picked up the pace. I said to him “I want you to cum in me, Dan.” I think this sent him over the edge, as he started shuddering as he came inside of me. He pumped himself into me a few times to get all of the cum out, and then lay on top of me, with his cock still in me. He lay there for 30 seconds or so, at which point I told him I had to get up to pee. I came back to bed, and he still seemed in shock over what happened. I asked him if he enjoyed himself, and he smiled and said yes. We chatted for a bit, and then drifted off to sleep.

The next morning, we both woke up and started chatting. I figured it was as good a time as any to introduce him to the wonders of morning sex, so I began making out with him and getting him hard. I rode him this time, and grabbed his hand to rub on my clit while I was on top. Before too long, I could tell he was close to cumming, so I started rubbing myself quickly to get off before he did. He came inside of me again, and I rolled over to lay next to him.

We talked for a bit longer, but it was getting late. We swapped numbers, and I asked him how much longer he was on Guam. He said he had another two weeks, and I told him that we’ll have to meet up again soon to try doggy style. I went downstairs and caught a cab back to my place; on the way, I texted Liz to let her know her plan was a success.

Source: reddit.com/r/gonewildstories/comments/w0frpr/my_friend_gets_me_to_take_a_guys_virginity_fm