[MM] How I [19M] lost my Anal Virginity to a Man [42M] Over Twice my Age Wearing my Girlfriend’s Clothes

I’ve changed some names and minor details and am using a throwaway to maintain anonymity. Otherwise, this story is 100% true and took place when I was 19.

To begin, I’ve almost always known I was bisexual. I’d experimented with guys in high school and sucked a few dicks. However, I had never gone all the way and actually been fucked. My experimenting with guys came to an end my senior year of high school when I got a girlfriend, and I didn’t have any sexual encounters with another man until my sophomore year of college when this story happens.
My sex life with my girlfriend (19 years old) was great. We ended up going to the same college together, so we saw each other very regularly. However, I always wanted to scratch that itch of losing my anal virginity to a man. So, during a particularly horny moment when gay porn wasn’t cutting it, I made a post on Reddit seeing if someone wanted to meet up. I immediately received a ton of messages, but after chatting with these guys over the course of about a week or so, most of them ended up flaking or being too creepy to actually want to meet up with. I was too nervous to try and hook up with someone from my school, since I didn’t want it to get out to my girlfriend that I was hooking up with other guys.

Just when I was about to give up hope, I got a message from Jeff. Jeff actually knew how to spell, and was polite and respectful about my wants and needs, and lived only an hour away from my school. He was 42 years old, and very good looking for his age. He had a slight dad bod, but obviously worked out since he was pretty muscular and had a large chest and shoulders. He had a nice trimmed, cut cock, which about 7 or so inches long and pretty average thickness.

Jeff and I hit it off almost immediately. Before this, I was already pretty submissive, but something about him awakened something inside of me. He had me sending him pictures of myself at all times of the day: I’d leave in the middle of my classes to send him pictures when he told me to, or I would sneak off to the bathroom for a quick ass picture when I was hanging out with my girlfriend. I was smitten.

Unfortunately, I couldn’t drive an hour away to meet him without arousing my girlfriend’s suspicion. Thankfully, she had a girl’s trip planned for the week of spring break, so Jeff and I planned to meet up then. But that was 2 agonizing months away.

During those two months, I completely submitted to Jeff. Whenever he would tell me to, I would send him pictures of myself. He made a rule that any time my girlfriend sent me a nude, I would pass it along to him – and I was so horny that I did it. He would always tell me how sexy my girlfriend was, and how sexy I would look wearing her lingerie for him. It got to the point where, whenever my girlfriend would send me a videos or pictures of her in her underwear or her naked, I would get more turned on by the thought of wearing it for Jeff or being in her position than my actual girlfriend.
At the same time, Jeff instituted a rule where the only porn I would be allowed to watch was sissy and crossdressing porn. So for 2 months, multiple times a day I would jerk off to men wearing women’s clothing getting fucked and imagine myself in their position. Not a minute of any day went by where I didn’t fantasize about wearing a sexy outfit for Jeff and letting him take me.

Eventually, spring break rolled around and Jeff and I were planning our meet up. As soon as my girlfriend left, I was going to leave for his place and spend a few days there. However, Jeff had a few instructions before I came to him. He sent me a screenshot from my girlfriend’s social media: a halloween post from the past year of her wearing a slutty schoolgirl outfit. Plaid skirt that showed her whole ass, white blouse, lacy red bra showing a lot of cleavage, knee socks – think classic slutty schoolgirl costume. Jeff gave me my task: I was to get my girlfriend to wear that outfit, fuck her in it, document it, and bring that outfit, along with some of her other clothing, with me to his place.
So I did it. The night before my girlfriend left on her trip, I spent the night at her place. I convinced her I wanted to do something special and got her to wear that outfit for me. I fucked her in it and I took pictures and videos of the whole thing. I was so turned on the entire time I was fucking her – but she didn’t know it was because I was imagining myself in her position.

As soon as she left the next morning, I took the outfit and some of her other clothes (a lot of lacy thongs, boyshorts, some bras, and some more skirts), locked her place up, and headed to Jeff’s place. The entire drive my heart was pounding so hard: I was an insane mixture of horny, scared, and excited.

When I got to Jeff’s place, I sent him a text that I was there. When he opened the door, he looked just like his pictures: a somewhat fit older man with a handsome face and broad shoulders. He invited me in and offered me a drink. We sat down on his living room couch and made some awkward small talk. After a few minutes, the small talk died down. That’s when he asked:

“Did you bring what I told you?”

I replied, “I did.”

He said, “Good. Go and change into the outfit and meet me in the bedroom. It’s upstairs on the right. There’s a bathroom in the room you can change in.”

So I did what he said. I went to the bedroom bathroom and changed into my girlfriend’s schoolgirl costume. Honestly, I looked pretty good. The bra didn’t fit me well, but I tied the shirt to show my midriff. The skirt showed my full ass and the red lace thong I was wearing underneath. The socks came to right below my knees.

When I left the bathroom, Jeff was in the room, setting up the TV. He looked at me and grinned and said, “You look sexy.” He had me send him all the pictures and videos of me and my girlfriend from the night before, and he put them on his laptop and shared them to the TV.

The first thing that popped up was a video of me fucking my girlfriend missionary on her bed. Her moans were coming through the speakers, and I could hear my balls slapping her thighs. I didn’t have a boner before from nerves, but I started to get hard. Jeff looked at the screen, then me, and said “That’s what I’m going to do to you. Now get on your knees.”

I got on my knees, and as I was getting down, he took his shirt off. He told me to undo his belt take his pants off, so I did. Out sprung his beautiful cock. I took it in my mouth and began to blow him. I licked up and down and got my throat as far down as I could. The whole time, he was putting pressure on the back of my head and kept telling saying, “Good girl.” This combined with hearing the video of my girlfriend getting fucked, turned me on so much that I was moaning on his cock.

Eventually, he told me to get on the bed on all fours and face the TV. I did exactly what he said and tried to stick my ass up and look sexy for him. He got a bottle of lube and began rubbing it on my ass, and slowly began fingering my whole and stroking my cock under my skirt. This, along with watching my girlfriend getting fucked on the screen, sent me over the edge and I immediately let out a girly moan and came all over the bed. Jeff laughed, and he grabbed the back of my hair, pulled my head back, and whispered in my ear, “Just because you finished doesn’t mean I am.”

He continued to finger me, eventually adding 2, 3 fingers. After what seemed like forever, he told me “It’s time,” and I knew I was about to lose my virginity. He rubbed more lube in my asshole, and I felt his cock push up against my hole. He put one hand on my waist and pushed in.

I let out a yelp and lurched forward. He pulled me back by my waist and leaned down into my ear:
“Shh, shh, the hard part’s over. Just relax and be a good girl like your girlfriend.”

I was already hard again at that point, and this got me even harder. I let out a moan.

For the next few minutes, he worked himself into my asshole, until he was eventually fully inside and I could feel his thighs on the back of mine. He sat there for a few minutes, rubbing his hands along my waist and cock. By this point, the TV had changed to a video of my girlfriend blowing me.

Jeff started to slowly thrust into me. Once I had relaxed to his cock, it started to feel good. He began to pick up speed, gripping my waist and pushing into me. I started to let out moans, which were only drowned out by the sound of my girlfriend slobbering on my cock.

Jeff started to thrust faster and more aggressively. I could hear him breathing harder, and my moans were getting louder. Eventually, it felt like something just clicked in me, and I started feeling waves of pleasure coursing through my body. my arms were shaking, and they collapsed and I fell on my face into the bed. Jeff continued to fuck me, hard. With every thrust, I let out a high pitched, girly squeal.
After what felt like hours of fucking, but couldn’t have been more than a few minutes at most, Jeff grabbed the back of my hair and yanked my face up to face the TV screen. I was fucking my girlfriend doggystyle.

“Look at your girlfriend. Look what I’m doing to you. Imagine if she saw you right now.”
This was too much for me. I couldn’t even speak I was in such ecstasy, but I let out a huge moan. Jeff said, “Turn over. I want to see your face when I cum.”

I did exactly as told. He flipped me over onto my back and began to jerk both of us off. He groaned and shot out huge ropes of cum all over my girlfriend’s costume and my face. I came then too, all over his hand and my outfit. I laid there dazed for a second, both of us panting and listening to my girlfriend moan, until Jeff put his cum covered thumb in my mouth. I took him by the wrist and licked all of my cum off his hand.

Jeff pulled his hand off my tongue, slapped my ass, and said “Good girl. Let’s go clean up.”
I hope you all enjoyed that story! I ended up staying the rest of the week at his place and hooked up with him throughout the years, so I have plenty more stories if there’s interest. DM’s are always welcome!

Source: reddit.com/r/gonewildstories/comments/yo0rja/mm_how_i_19m_lost_my_anal_virginity_to_a_man_42m