[M] Reddit Helped Me Lose My Virginity

If you want a part one to this, I have a post on my profile called “A Story of Failure’. It basically details my experience with trying to find a hookup through Reddit and the defeat of being ghosted.

I spend a while giving backstory. If you want to skip to the “hot stuff” scroll about halfway down.

During March of this year, I ended a 2 year relationship with my ex. It felt like the end of the world to me. I had fallen so hard for this girl, only to see COVID and long distance slowly tear our relationship to shreds.

I spent the following summer picking up the pieces. I kept my head down and did my best to enjoy myself while recovering. One of the biggest realizations was how much I missed out on when it came to my own personal development and self-discovery. My ex and I weren’t ready to have sex during our relationship, so I was still a virgin, with barely any experience at all. During high school I prided myself on being a ‘good boy’. I never drank, never smoked. I didn’t even stay out later than midnight. I wanted to change that. So I turned to Reddit.

After months of posting, talking to people and having plans fall through, being ghosted and ignored, I finally got a message from a random redditor.

>Hey whats your story bud? We are 33 year old experienced swingers who may be able to help.

It felt surreal. On one hand I was doubting it would go anywhere due to the many times Reddit failed for me, but on the other, I was still hopeful that this would be my chance. I told them about myself and what I was looking for. Surprisingly enough I fit the criteria they were looking for as well, so we started talking more.

He wanted a young guy to teach. He wasn’t really interested in me sexually, and I felt the same. After all of his experience and personal growth, he felt a responsibility to pass it down and help someone out. I was looking to learn as much as possible, and to finally get the experiences that I missed out on. It ended up being the perfect relationship. To this day I see him as my awesome sexual guru mentor.

They were endlessly nice and cordial, doing their best to be polite and welcoming in every way. We actually had a ton in common; even being from different generations, we both had the same timeless nerdy interests. It was super comforting to be able to be friends with them before doing anything.

They were very experienced with meeting people online, so they made every precaution to make sure that we’d all be safe going through this experience. I met with the husband first in a public place. It was to verify that we were both real people and that we weren’t a danger to each other’s personal lives. We had a deep conversation about why we were both interested in what we were doing. He told me about an old friend of his that died a virgin. He felt bad that he could’ve helped his friend pop his cherry, but was too afraid to bring up his swinger hobby. To him, it felt that if he helped out someone else, it would fill that karmic debt that he owed to his friend. I was surprised at the level of honesty coming from him and was glad to maybe help him with that debt. I told him about my recent breakup and how I felt like I needed to go out and experience more. We talked about my problems with self-confidence and how I no longer wanted to be a super uptight goody-two-shoes.

We hit it off pretty well. He even showed me some of his previous adventures in the swinger community. Videos and pictures of him and his wife having fun with other unicorns and swinger couples. It was crazy that I was getting myself into this, but I was so ready for it. We chose a date and he let me start talking to his wife.

From then on we’d build up the excitement. We had about a week or so until we had a free day to meet. Almost every day leading up to it, we would tease each other with sexting and talking. It was so easy to get turned on by her. She was exactly the type of girl that I wanted to meet for myself. Confident, funny, nerdy and so unbelievably sexy. There was one night I was out with friends, and she did everything in her power to get me horny for her. I had to cover my bulge in my laptop and journals to avoid anyone seeing me get hard from the pictures I was getting on my phone.

Eventually it was the day. I prepared in all the ways that the internet told me to. I stayed hydrated, shaved and kept myself clean to make sure that I’d be ready for the night of fun that I was about to get into. I even bought them a candle as a little gift. When the time finally came I got in my car and started driving to the first step in a long journey for me.

I met with the wife at a restaurant near their house. They didn’t give out their address directly to first timers, so I’d follow her home from there. We went into the restaurant and finally got the chance to get to know each other face to face. Given how nervous I was, it really helped me settle into things. It felt so strange being on a date with an older woman like that. I kept thinking about how exciting it was to be a young stud out with a hot milf like that. All the onlookers would be curious as to what was going on between us, little did they know she was about to turn me into a man.

We finished dinner and headed to our cars. I followed her to their home blasting Def Leppard to get my mind and body hyped and ready. We finally got the house and she let me in.

We spent a bit of time talking before they led me up to their room. It was set up so nicely, with candles and lights decorating the room in a way that was so relaxing. They gave me snacks and drinks to enjoy. They even let me smoke a little pot with them. I only did one hit because I was unfamiliar with the stuff, but it was one of many firsts I would have that night. They were so accommodating and so generous, it was clear that I was in good hands and that these people were worth every moment I had with them.

Even then, I was still nervous. After all, it would be my first time having sex. It would be my first time doing anything out of the ordinary at all. I was about to lose my virginity in a threesome with a married man and his beautiful wife. I could barely believe that I was in the position that I was in. I think they picked up on that, so they really let me ease into things.

We spent the better part of an hour just talking. We talked about life, about our experiences, and our common interests. It was so much fun even just getting to know them. Hearing their story of how they first met and all the amazing experiences they’ve had since showed me how lucky I was to meet such great people. It taught me so much about the world and relationships. I was initially skeptical of how swinger relationships could work, but after seeing the deep connection and love that these two had, it was clear that nothing could get in between them. The sex was a way for them to have fun, it wouldn’t complicate things at all. Even after all their experiences, they still wanted each other. It was beautiful and inspiring.

As I slowly started to get more comfortable, we drew closer. She started to run her hands across my body. I felt her fingers slide down my chest and she slipped her hands under my shirt. I pulled her closer and played with her hair. I caressed her milky skin and looked at her with hungry eyes. All the while we were still talking, letting the light touching build up the tension. Eventually she cut me off mid sentence, pulling her face onto mine. She was aggressive, I think the long wait made her insatiable. She was kissing me with ferocity, taking her hands and grabbing the hair on the back of my head, pulling me closer and deeper into the kiss. She then brought her attention to my clothes, we both had our tops off pretty quickly. I let my hands explore her body, feeling her stomach all the way up to her wonderful breasts and her sexy pierced nipples.

She started messing with my belt until I got up and undid it myself. Then she led me over to the bed. It was so hot, she knew exactly what she wanted to do with me. She didn’t tell me yet, but her plan was to give me the best first blowjob ever. She wanted me to cum as quickly as she could make me.

She laid me down on my back and helped me take my pants off. Her lips wrapped around my dick softly as she slowly wet my whole shaft. That night I got the full service blowjob of a lifetime. I barely knew what to do with myself, it felt both uncomfortable and new, but it also felt fucking amazing. Her experience with sex was really showing. She used her tongue with my dick in her mouth, swirling it around to give me such an orgasmic sensation. She let out little moans of pleasure while she was going (hearing that a woman is turned on makes me so much hornier). She teased the head with her tongue and licked up and down my shaft. Her head bobbed up and down as she got faster. My body was tensing from the feeling of immense pleasure. I did my best to be attentive to her, I held her hair up out of her face and massaged it whenever she made me feel good. She even took it all the way in, pressing her lips to the base of my dick. I could feel the warmness of the back of her throat. The way my cock felt with her taking it all in was phenomenal, and it took me closer and closer to cumming. It didn’t take long before I couldn’t take it anymore. I started to breathe heavily and moan, she noticed and knew what to do. Before I knew it, she was getting more intense with it, playing with my balls and giving my dick the ultimate treatment. She got faster and faster until I came inside of her mouth. I barely even got a chance to warn her. I apologized for not saying anything before I came. She swallowed my cum and told me not to worry, she loved the way I tasted.

After that I needed some time to gather myself again, but I wasn’t about to let that stop me. I intended on returning the favor, so I laid her on her back. I made sure to prepare for this, I put a lot of time researching how to pleasure a woman by eating her out. I wanted her to feel as good as she made me feel. I have experience as a woodwind player as well, so I’m adept with my tongue. With tips from the husband, I went for it. I started on her tits, kissing and groping them. I traced my tongue on every inch of her breasts, sucking and using my tongue to play with her pierced nipples.

I slowly made my way down her body, kissing a line down from her chest. I spent a fleeting moment kissing the edges of her warmth before drawing back and kissing her down each leg, letting my breath catch over her pussy as I went from one leg to the next so she could feel the moist hotness of my mouth for just a brief moment. I made my way down her leg again back to her beautiful pussy, and started licking the outside. I kept my tongue wide and flat as I licked both sides, then I relaxed my tongue as I started to lightly lick her clit.

I started gently, rubbing it softly with the tip of my tongue. She was so wet already, it was a light taste that had me wanting more. I started to go faster, trying different methods to see what made her want it more. Her husband guided me through what to do, telling me to put a finger in her after a bit, and how to notice when she liked what I was doing. I got better and better until she started loving it. She started grinding on my face and moaning, I shoved my face deeper into her and went faster and faster. My tongue started to get sore from the speed I was going at, but I heard her moans of pleasure and knew I couldn’t stop. I pushed past it and kept going, I didn’t stop until she was shaking and yelling in ecstasy. I think I made her cum with just my mouth twice that night. She told me whatever girl I found on campus would be lucky with a guy that could eat pussy like me. The compliments really helped me with my confidence as I got more comfortable.

From there we started to get the condoms out. They showed me how to put it on properly without accidentally breaking it or putting it on the wrong way. They also told me the correct way to pull out with a condom to keep the cum inside with no mistakes. I was still a little soft, maybe only a half boner. Her husband demanded that she get me hard. He told me not to be worried about asking my partner if I needed help to get hard. She sucked me off a little more until I was erect, then helped me put the condom on.

I was so excited to finally feel my first time. She lubed me up a bit with her spit and she guided me into her. The feeling of the walls of her vagina was amazing. I could feel every part of my dick enveloped in her, it rubbed against the walls and edges giving me small sensations throughout.

We fucked for a while. We went from her riding me, to doggy style, the leap frog, reverse cowgirl, to missionary. As I was going, her husband gave me tips on how to fuck her better. He showed me how to grab her by the hips so I could fuck her harder. He taught me how to spank her the right way, and how to caress her and make her feel rewarded afterwards. After some time he got a little worked up himself, so he grabbed her for a turn. We spitroasted her, him fucking her juicy pussy and me fucking her mouth. If I remember correctly I went through two condoms, finishing inside her with the condom on both times.

Eventually it got pretty late and we’d all satisfied ourselves for the night. I cleaned up a bit and got my clothes on. They asked me if I enjoyed myself and had fun, and of course I told them I did. They even gave me a snack for the road, it was adorable. I left with one last kiss from the wife and was on my way, feeling like a new man.

In the coming months after that, I turned over a new leaf. I decided to do all the things that I wanted to do that I felt like I missed out on before. When I went off to college I tried alcohol for the first time, I did weed again and actually got high, I went to my first party and I had a one-night stand.

I also kept in touch with the couple, we’re good friends to this day. I’d tell them about certain parts of my life and they support me and give me advice towards building up my confidence and character. I even visited them again over thanksgiving break when I was home from school. I got to tell them about all my crazy adventures I’ve been having at school and got to show them some of the things I’ve learned out in the field.

TLDR: I lost my virginity to a 30-something swinger couple that I found on Reddit.

Source: reddit.com/r/gonewildstories/comments/rhcxf4/m_reddit_helped_me_lose_my_virginity