I went into my last semester of college begrudgingly accepting the fact that I would not lose my virginity during my time there despite my ok looks and decent build. I had never been one to party. That fact and the combination of my shyness around romantic and sexual matters, my former religious devotion, and now Covid meant that my opportunities to approach a woman romantically or sexually were slim to none.
But I guess life finds a way.
Shortly after the semester started I, out of horniness and loneliness, decided to put up a personal ad on Craigslist explaining that I was a virgin. I had to word it very vaguely, but I eventually was able to get across that I was looking to experience my first time with a woman.
As I should’ve expected, I mainly got replies from men telling me how it’s not gay if it’s just a blow job, that it’s the same as if a woman were doing it, etc. I was disappointed despite deciding beforehand to not get my hopes up and decided to give it only one more day. And then I got an email from Todd.
Todd emailed me saying that he and his girlified, Mary, liked to have guys over to have some fun with her, no guy on guy contact, and that when they were looking at my ad, Mary had told him that she actually wanted to take a guy’s virginity. I could not believe my luck! I typed faster than I ever had in my life to reply to Todd saying that I was definitely interested in them as well!
We emailed back and fort for a little bit, with Mary jumping in occasionally on Todd’s email. We took turns telling each other about ourselves. I found out that Todd was 35 and Mary was 33. Eventually, we exchanged pictures back and forth, clothed of course. Mary had shoulder length dirty blond hair that was almost a little wispy. In the picture she was wearing a dark navy blue lingerie top with bright blue ribbons in a bow on top. It was enough to get me excited. After that, we quickly settled on a date and time, the next Friday at 9 pm, and exchanged phone numbers.
I could not wait for Friday to come around. My classes seemed to slow down to a turtle’s pace as the days slowly ticked by until, finally, it was Friday. That morning I shaved my balls for only the second time in my life, the first time was to see just what it was like, as I prepared for that evening. After dinner that evening, I hurried back to my dorm room and quickly showered and brushed my teeth multiple times. I waited eagerly until 8 when I got the text with their address.
I left at 8:45 in my car, my heart pounding faster than it ever had before. I sat for a couple minutes in my car parked on the street psyching myself up before I got up and made my way over to the door. I hesitated for a second, then knocked three times.
Almost immediately, the door opened and I found myself face to face with Mary. She was wearing a bathrobe and, now that I was meeting her in person, I realized two things: Mary was about a head shorter than me and she wasn’t wearing a shirt or bra under her robe. Before I could really say anything or react, she pulled me into a tight hug that under any other circumstances would have been embarrassing due to my boner. Instead she just let out a small giggle and took me inside to their living room.
Holding my hand, Mary led me over to the living room where she sat down next to Todd on the couch. As I sat down in the chair next to the couch, we began to talk. It was innocent stuff at first, I got to learn more about them and vice versa. Really I think they could just tell that I was nervous, my legs were probably shaking a lot, and they just wanted to give me time to calm down and get used to them.
Eventually, Todd whispered something in Mary’s ear and then got up to go get some drinks. After he had left the room, Mary beckoned me over, patting right next to her on the couch for me to sit. I slowly got up, trying to hide my boner for whatever reason, and slowly made my way over and sat down. However nervous I was before then, I was triply so now. But I forced myself to look at her, at the woman that I knew I was going to fuck that night, and continue on with the evening.
Mary asked me what I found attractive about her. I answered her truthfully and admitted that it was the shape of her body, her boobs specifically, and also her age. She seemed a little surprised at that and told me that I must be joking, being in college with all the “pretty college gals” around me. I told her that was fair and that there were many attractive girls at my school, but that I had found that I was more attracted to older women, or at least women older than me.
Mary paused, then giggled at that. She then put her hand on my thigh and said “I guess you’re lucky you found me then.”
Throughout all this, I had been mostly hard, my nervousness preventing me from being fully so. But when Mary said that, my dick twitched hard enough that Mary could see the movement through my jeans. She giggled at that as well. “Someone’s a little excited,” she remarked. I laughed a little nervously at that, not fully sure what to do in that situation. Mary picked up on this and told me to relax. She then put her hand on my cheek and turned my face to hers. I looked at her, transfixed by something in the way she looked at me. I could feel some sort of shared desire between us. And then, she leaned forward slowly and kissed me.
I had kissed before with my high school girlfriend, but that had always be chaste pecks on the lips, stolen in secret when we were sure no one was looking. This kiss was deep and full of desire. My tongue intertwined with hers back and forth cyclically until we finally parted. My eyes opened slowly and I looked at her again. Her eyes were still closed, as though she were savoring the moment still. As she was doing that, I spied Todd in the door frame, one hand holding a beer, the other down his pants slowly going back and forth. He saw me looking and pressed a finger to his lips, then pointed me back towards Mary and gave me a thumbs up.
I turned back towards Mary as she opened her eyes. She had an expression of satisfaction on her face, but it was quickly replaced with that desire from before. “That was great, and it only gets better from here,” she said. “Are you ready for more?” I nodded a little hesitantly and she smiled. Mary leaned in for another kiss. But this time as I leaned in, she took my hands in hers and placed them on her tits, over her robe.
Boobs are amazing, at least in my experience. They were just so heavy, in a good way. And as Mary kissed me deeply, I started squeezing her boobs gently at first, and then gently playing with them. As I started playing rougher with them, Mary broke the kiss and started to moan in time to my movements. Slowly, she lifted her hands up and opened her robe so that I was touching her skin directly now. I could feel her bare nipples against my palms, how hard they were as I squeezed back and forth.
After a little while of this, kissing intermittently all the while, Mary reached out to grab at my crotch. She started rubbing my dick back and forth against my leg as I continued to feel her up. Then she pushed me back so I was lying against the side of the couch.
Mary reached up to the top of my jeans. She undid the button carefully and then slowly dragged the zipper down revealing my bright blue boxer briefs. She giggled when my dick bounced up as she pulled my jeans off and then made her way back up to in between my legs. She started rubbing it again, as though she were transfixed with its hardness. Then she pulled down my boxer briefs, and put my cock in her mouth.
Had I not jerked off earlier that day, I probably would have cum immediately in Mary’s mouth. As it was, it was all I could do to hold on as Mary began to bob up and down slowly, her hair silkily falling on my legs. I don’t think Mary had even sucked me off for three minutes before I came in her mouth. She swallowed every bit of cum as I came and then continued to suck for a couple seconds after, as though she were looking for even more.
At this point Todd made his reappearance, well reappearance to Mary at least. But she’d probably known that he’d been watching. She wasn’t surprised at the very least, which confirmed my suspicion. Todd helped Mary up off the couch and kissed her deeply, just as I had a few minutes before. As she broke away, Mary looked back towards me and smiled devilishly. She grabbed my hand in hers and then led us both to their bedroom.
Their bedroom was decorated in a comfortable theme. All over their walls they had different designs obviously painted except for the one wall that held a draping and a TV. The most surprising thing about the room though was the stripper pole set up in it. The pole itself didn’t appear to be bolted down but rather fastened with a weird hook system. I didn’t know exactly what to make of it, so I just decided to let it go with the flow.
Mary sat us both on the bed and then made her way over to the pole. She then dropped her bathrobe, revealing her half naked form, her panties still on. Then, Mary began to dance for us around the pole. It was erotic as I had never experienced before. I was quick to start masturbating, which Mary seemed to smile at. Her boobs bounced up and down as she danced around the pole. Eventually, Mary got close to us as we sat on the bed. And as I stared at her beautiful voluptuous body, Mary stripped of her panties and I saw my first pussy in real life.
As I stared in wonder, Mary giggled again and crawled up onto the bed between Todd and I. And then she took both our cocks in her hands and starting stroking us up and down. After a couple seconds I was completely hard again, fully recovered and ready to go. And Mary was ready to go as well. She got up and squatted over me before lowering herself onto my cock. And then suddenly, I was inside her.
To be continued in part 2
Source: reddit.com/r/gonewildstories/comments/ob9ry8/how_i_lost_my_virginity_to_a_couple_mfm_part_1
Hot!