FYI this is super long and there’s a lot of build up, which might not be your thing, so sorry about that.
I’ve been in a bit of slump, sexually speaking. I spend a good amount of my 20s having all kinds of risky sex with mostly strangers. I don’t regret any of it, in fact, I miss it. I started getting a little more cautious and went from MDMA fueled orgies in Montreal to basically only having sex with myself because suddenly I’m too anxious to meet up with a stranger for sex. I decided this was fine for a while, that I didn’t need to do anything crazy to get off, that it wasn’t worth the risk. I’ve been ignoring all the urges and fantasies that I used to give in to on a regular basis, I’ve become…normal.
I think the worst thing you can do is be normal. What’s next? Marriage? Home ownership? A car that wasn’t given to me out of pity by an elderly family member?? Fuck that.
So at this point, I’m more motivated by the thought of becoming average than I am about fulfilling any kind of fantasy I’ve been having. Usually I’ll have a very specific fantasy in mine for weeks before any kind of particularly crazy sexual encounter, taking my time to plan it all out. This time my mind was all mixed up, I had so many things in mind that just didn’t go together, what I was thinking would be the equivalent of a week of non-stop hookups. I basically just wanted to try everything I’ve never tried, all at the same time.
It was too much, I had to focus and figure out something I could do in one go that would satisfy this urge I was having. I wanted to something kinky, something I’ve never really done, and something that you’d consider rather risky. If you’ve read any other posts of mine, you might know I’ve had my fair share of paid sexual experiences. My logic being it was the best way to get quality D without any bullshit. Since I live near Montreal, I could go there every so often and do it legally. Since I couldn’t afford to go to Canada, I decided I’d see if I could find anyone online.
Backpage was a bust, their escort section is gone and although you can find lots of women offering “massages”, none of it was what I was looking for. I tried Craigslist and just searching Google, but none of it felt right to me. It had been so long that I just couldn’t navigate the territory anymore. I thought I’d have to give up.
After basically giving in altogether, I decided to go home, get drunk on box wine, and get creepy on Facebook.
I have a friend who is very…like minded. We’ll call her “S.” We’ve even hooked up a few times. The first girl I kissed was her, the first time I used a strap-on was with her, and the first time I had a three way, she was there. It had been a while, but I thought reaching out to her might help. I didn’t necessarily want to hook up with her specifically, but I thought she might be able to inspire me.
So I message her and tell her my dilemma. We get to talking and we start talking about a guy I who’s virginity I took a while back (see my post history). She said that she was envious of my experience and wanted to do something similar. Instantly I knew what I wanted. I wanted her to take another guy’s virginity in front of me. I wanted to coach him while he fucked her. I wanted to see what his face looked like during his first orgasm with another person. I thought I could even help, if I got the urge.
So we started plotting…
I didn’t know any other virgins besides my friend from before who was no longer one since I fucked him in a cheap motel, so we had to dig deep. I looked around FB, hoping to find someone who seemed good, but then I remembered that people don’t usually talk about their virginity in their FB profiles, so I was just wasting time. So I took to Craigslist…
I put up an ad, looking for a virgin guy who was down to lose it to two slightly older women. By the next day, the ad had been taken down and marked as spam, but that didn’t stop about two hundred guys from messaging me. I sifted through all of them and responded to maybe a dozen. The one that caught my eye was a guy saying he just had his 18th birthday and wanted to lose his virginity before he graduated high school. After confirming his age and checking out his facebook page, I decided he was the one. Even if he wasn’t a virgin, I really didn’t care, I liked his look.
S was excited to the point of going shopping for the occasion. We took to the mall and stocked up. We got matching high heels, stockings, and guarder belts (black on black on black), a new dress each (black, duh), and of course, mani pedis…
Throughout the day we loosely planned our night with this guy. S threw down on a hotel room near by, so after shopping, we went there and waited for him. It was only about 7pm and we weren’t going to see him for about three hours, so naturally, before we changed and got all dolled up, we sipped red wine while she ate my pussy.
She’s really good too. I’m not a fan of pussy eating; frankly, vaginas scare me, even my own, so I’m not a fan of going down there, but god dammit I love getting eaten out by a girl who knows what she’s doing.
I came three or four times while she was down there before we decided to start getting ready. She decided she’d hold off on having her orgasm(s) until our virgin arrived.
Once we were all showered and dressed, we waited eagerly for him to show up. Thankfully, I got a text about 30 minutes before he was supposed to get there, asking if he could come by now, which was obviously okay with us. About 5 minutes later, we hear a knock at the door.
We both answered the door and let him in, locking the door behind us. He was your average awkward white teenager. Tall, kind of gangly, no facial hair to speak of, blonde, and reeking of weed. I asked if he was nervous and if he admitted he was. He had been in his car smoking pot, trying to calm down. I asked if he wanted to smoke more, which he did.
I don’t smoke, as I work with kids, but S does, so she shared a couple bowls with him as we talked about what was going to happen. At one point, S was sitting next to, let’s call him “V”, on the bed and I decided to make out with her in front of his face.
As we sloppily kissed, I put my hand on V’s crotch. I could feel his dick getting hard quickly. I hadn’t touched a cock in a while and it really got me going, without even thinking, I pulled his dick out and put it in my mouth.
I feel like you can guess what happened next…
After about 3 seconds, he pulls back, he’s holding the head of his cock tightly in a desperate attempt to hold in his cum, but it wasn’t going to stop. I said to let it go because I wanted to see it. He started to jerk off as the rest of the cum came down his cock. I didn’t want him to feel bad, so started licking the cum off his cock and balls. I opened my mouth to show him his cum, when I did that, S grabbed my face and kissed me hard. We swirled V’s cum around our mouths and started groping eachother. I had S lay in V’s lap while I fingered her. She took his now soft cock in her mouth and sucked it as she moaned and moaned. After a little while, she said to stop because she wanted to cum on V’s cock.
She got on her knees and started really taking V’s dick deep. Gagging on it and drooling all over his already cum soaked balls. Once his dick was good and hard, she had him lay flat so she could ride it. I helped guide the tip in as she got on top. She apparently forgot he was a virgin, just like I did before, and started really riding him hard. She started by rocking her hips back and forth, but quickly got on her feet and squatted over him. At that point, he said to stop since he was going to cum, to which I responded, “that’s fine, just fuck her!”.
Now it sounds a little insensitive, but I know S and I mostly know how dicks work, and I knew that we weren’t going to help him learn to control his orgasms right then and there. This guy seemed like he could get hard fast and probably go a few times, so I figured he’d be better off fucking S as hard as he can for a few seconds and getting her off, than trying to hold back his cum and making things boring for S.
He seemed to somehow understand my logic and really started to give it to S as she squatted over him with her hands on his chest. I got a great view of his now soaking wet cock pounding my friend’s pussy that I will forever fantasize about and after maybe 15 seconds, both V and S exploded. S is a squirter and started gushing all over V. The bed was a mess, S was a mess, V was a mess, but I still wanted more. Yes I had gotten off with S earlier, but seeing her get pounded like that made me want that for myself so badly.
As the two of them were recovering, I asked V if he had any more energy. He said he was happy to keep going, but thought he couldn’t get it up. I love a challenge, so I got to work. This time, he and S made out as I sucked his dick. He was still soft until she started kissing his neck and chest all over. He started to moan and I could feel the blood pumping into his cock. Once it was hard enough, I hopped on. I wanted him to fuck me like he fucked her, but since my legs are not nearly strong enough to squat like she was, I just leaned way forward to give him some room to pound me.
Once we got situated, I told him to just fuck me as hard has he could until he came. He started fast right off the bat, just hammering my pussy, I could feel his balls slapping my ass and S’s hand fondling my tits. I started getting that familiar feeling as I tensed up and started mildly convulsing on V’s cock. He managed to keep up his jackhammer pace for what seemed like a good 60 seconds or so, that might be way off, but it was definitely enough time to have a huge orgasm. After I was done cumming, I could see in his face that he was about to as well. He started slowing down, so I took the opportunity to let S have some fun too.
We got down on our knees side by side and told V to cum on our faces. Granted, the poor guy was on his third orgasm and it was possible it would just shoot a blank, but I wanted S and I to suck his cock together, something we’ve never done. So we started blowing him, one of would take his cock, the other his balls, and then we’d switch. Sometimes we’d both work the shaft and kind of make out on his cock. It was honestly one of the greatest things I’ve ever experienced. I don’t like making out with guys that much, but I love kissing S, her lips are so soft and that coupled with this guy’s cock made for such a great experience.
It wasn’t long until he said he was cumming. We both eagerly awaited his load as he jerked off an inch from our faces. Miraculously, he came again. It wasn’t much, but he got smear it all over S’s face and I licked it off.
Once we cleaned up, V thanked us and left. S and I decided to stay in the room for the night. We had some dinner and talked about what had just went down. We got ourselves all worked up again and decided to masturbate next to each other. We searched for porn together until we found something we both liked. After about 2 minutes of mutual masturbation, we realized how bad we wanted to fuck eachother, so she went down on me again.
This time, she lubed up her fingers and went in my ass. I don’t think there’s anything better. I lost track of time and I also lost count of my orgasms. All I know is the sun was coming up by the time she stopped. Instead of sleeping until checkout at noon, we decided to each head home. When I got back to my place, I couldn’t stop thinking about S’s mouth on my pussy. I got myself off once more and finally fell asleep.
It was messy, awkward, not at all as expected, and just so much fucking fun. I’m glad I’m back.
Source: reddit.com/r/gonewildstories/comments/61danu/ffm_tag_team_virgin_slaying
Now that story of a life time!
That was so fucking hot! What a way to lose your v-card! Damn V is one lucky son of a bitch!
The two of you are doing the Lord’s work.
I’ve missed your stories!