My first time. AKA How I lost my virginity to a couple. [MFM]

This happened recently, last week actually, so I’ll do my best to describe in detail what happened in an entertaining way. I’ll do my best to not exaggerate but I cannot promise 100 percent the truth. It exists out there, but it’s a combination of all of our stories, not just my own, and I can’t claim to represent it.

Not too long ago, as a horny 20 year old college virgin, I discovered this wonderful, or terrible depending on your experience and/or view of such things, website called Doublelist. It essentially is an alternative to what Craigslist used to be (or at least that is what the risky online sites told me). It was on this very site, Doublelist, that I saw an ad while looking through the couple’s section that asked for a “young stud” for that evening. Being in a particularly horny mood and feeling reckless, I emailed them through an “alt” email I had previously set up with a simple description of myself and an enclosed pic of my bare chest. To my surprise, I received an email back almost immediately from the wife who had posted the ad. She told me that she enjoyed my pic and asked if I had a Kik. I responded back with my username, and soon we were texting back and forth. After a little bit, in which I had learned their names, Penny (39) and Matt (42), and had traded some pictures back and forth, Penny decided that I seemed nice enough online and decided to invite me over to their house.

After a 30 minute drive that seemed to take forever, worsened more by my nerves that had me shaking, I arrived at their house and was welcomed by Penny and Matt into their basement. They started a space heater as the night drained away the heat of the day and started to engage with me in small talk. Looking back now, they knew I was nervous, I must have been shaking like a leaf, and wanted to calm down my nerves. We talked for about an hour, Penny occasionally going up to make sure her kids were actually doing their homework. After Penny had finished smoking about three cigarettes and we had talked about everything from politics, there were more Democratic candidates still, to tv shows, Penny and Matt decided it was time to take things to the bedroom.

We got into the bedroom and they invited me to put my stuff on a chair and come onto the bed with them. So, we did, Matt on the left side of the bed, Penny in the middle, and me, less nervous, sitting next to her, all of us still wearing clothes. Almost immediately, Matt put on some gangbang porn, it was very clear the kind of stuff he was into. As he started watching it, Penny got out her laptop and asked me what I liked. Bashfully, I told her I preferred a lot of mom-son stuff and she pulled up a porn site and we perused the options before picking a Russian one with a redheaded milf. We watched this for a couple of minutes while I awkwardly tried to figure out if it was ok for me to touch Penny, finally just deciding to lean my head against her and put my hand on her leg near her knee.

After a little bit of this, Penny went out to make sure her kids were in bed before we actually started having fun. Matt and I talked a little bit about how the Russians in the porn video were over acting while we waited for her to come back. And when she came back, Penny had dressed up for me, not something I had expected. She had stopped in the nearby bathroom to change into a sexy teacher/mom outfit, having prepared it earlier. She was wearing a skirt with a dress shirt/blouse barely tucked in and buttoned up so that you could see her cleavage in her bra.

After her big entrance, Penny climbed back into bed between us and encouraged us both to take off our shirts. She started the next video on her laptop, the last one had ended, and I went back to leaning on her with my hand on her leg. I became more adventurous, my other hand looping behind her and grabbing her waist. And then up. Slowly. And then I was touching her left boob, over the bra and blouse. She giggled a little bit at that and and me what my first boob was like. And I answered truthfully; it was nice, but I couldn’t feel much other than the texture of the bra and the blouse. So she had me take them off, and I saw why men do anything for boobs. They were a work of art, like a commission that Michelangelo had been given from God himself. I did what any man does when having upon the nude female form for the first time does. I stared, until Penny reminded me that I could touch her too. And I did, grasping her breasts at first softly and then more firmly, even daring to eventually latch onto her right with my mouth. It was so much a new experience that I almost missed Penny jerking off Matt, but it came to the foreground of my thought as she reached into my shorts and underwear for my cock with her other hand.

After Penny had jerked me and her husband for a little while as we played with her boobs, Matt having joined in after a little while, Penny decided it was time for a little something more. She had Matt and I remove from her lower body her skirt. After noticing and bring entranced by her lack of underwear and bare pussy, I was brought back to reality by Matt asking me to do the honors as he poured oil on Penny. Not one to give up a good opportunity, I gladly spread the oil over Penny’s body, from her magnificent boobs, to her mom’s belly, to her already wet pussy. After repositioning ourselves on the bed, Matt pushed inside his wife as I caressed her boobs and rubbed her clit while she jerked me cock. Matt would thrust inside Penny, sometimes rhythmically, sometimes holding off for a big thrust at seemingly random. Meanwhile, Penny began to suck my cock as I caressed her body. It was a titillating experience which I do not think I could give justice to with any description other than it was awesome. After a couple minutes of this, Matt pulled out of Penny and whispered something to her. Laughing a little, Penny looked at me and smiled and asked me if I wanted to fuck Mommy.

I put on a condom, having grabbed one from the drawer Matt pointed me too, and prepared to enter Penny, now my mother, in missionary. I hesitated there before pushing in slowly. It felt amazing, even through the condom, as I started to push in and out of Penny, who kept telling me to fuck Mommy. It was a little awkward, I fell out once and had to reposition, but in the end, I came after a little while, respectable, and had fucked my mommy.

After that, we all lay there for a while, making the barest of conversation as we basked in what had just happened. Eventually, we got up and got dressed again. Penny led me to the door and we both thanked each other for the experience and said our goodbyes. And I left, returning back to my dorm room, listening to NPR on the way home.

Source: reddit.com/r/gonewildstories/comments/fe8qt1/my_first_time_aka_how_i_lost_my_virginity_to_a