My first cross dressing experience led to my first gay experience [MM]

This happened quite a few years ago when I was 19. Up until this event, I was pretty bi-curious but, coming from a small country village, didn’t have the means or ability to explore that curiosity. This happened my first year at uni.

I’d done my best from starting at Uni to be a social butterfly. I accepted any and all invites to party, spent probably far too much time in the pub and I made a lot of friends. There was one, we’ll call him Rick, who I was especially enamoured with. He was tall, muscly, with a little chin beard and long hair. We struck up a great friendship but I never had the courage to tell him just how attracted to him I was. I, for the sake of comparison, was a clear 6 inches shorter than him, rather slim and basically his exact opposite.

I [M] met with a trans [TF]for the first time tonight

So tonight I had my first gay sexual experience and it was with a trans girl. I was really nervous at first tonight but went I went her home I started to calm down a bit since I felt kinda wrong at first for doing this and all but I pushed thru. We set down talked for a minute and then started to kiss.

Once we really get kissing I reach down and start to touch her and after that all my worries went away and I just accepted that I am bi and this is who I am.

I then kiss her down her body to her dick and started to suck on it and loved it so much. Then we do a bit more kissing and then we go to her bedroom. I get on top of her first and confess that I can be dom or sub which I lean more towards and she says she never really has dommed before but I go down on her again and we play with each other and what not.

Hailey Gets Some Help [fff] [Masturbation]

My two friends and I climbed up the stairs to my room after a quick orgy at my sexy black neighbor’s house. Y’know, like ya do. We originally went over for ice cream, but one thing led to another and the three of us took turns blowing him until eventually my friend Courtney took his massive dick for a ride followed by Jasmine. Being the stud my neighbor is, he managed to blow two loads and filled both of them to the brim with cum. Unfortunately for me, we had to go before I got any for myself.

“Seriously, if you don’t marry that man, I will,” my friend Courtney said. Both she and Jasmine were walking like they’d just spent the better part of the day riding a horse bareback. I guess in some ways they had.

“I can’t believe we just did that,” Jasmine said, flopping down onto my bed to relax.

“Yeah, me neither,” I replied as I flopped down next to her.

“Can I borrow a fresh pair of undies? I’m leaking,” Courtney said.

“Yeah, you probably will till tomorrow. He’s a heavy cummer,” I said matter-of-factly, “Top left drawer, help yourself.”

How I lost my virginity to a MILF as a gay teenage boy [MF] [Pizza Delivery] [Seduction]

During my late teens (19yo), I used to work as a delivery boy. It was in a small town, filled with lovely and well-decorated houses. I worked for the main pizza company in town, so we got a *lot* of customers from all over the place. At the time, I had a boyfriend. We had been together for a couple months already.

Anyways, I used to work the night shift, and during a hot summer night, we got a call from a house I had never delivered to before. It was on the outer side of town, but didn’t feel creepy or dangerous, I didn’t give it much thought. So, I got the pizza, and drove all the way down to this place. It was a very big, white and brown mansion, with a pool and a huge garden. I ringed the bell, and a lady answered, and told me to wait while she looks for the keys. She opened the door, wearing only a bathrobe that outlined the edge of her breasts. She was tall, light brown hair, thick lips with red lipstick on them, and makeup on.

Bribed by my Coworker Part 2 [MF]

I’ve received a bunch of messages asking for what happened next in my story, so here’s what happened after Jessie went on her vacation. If you haven’t read part one, here’s the link:

I 24[M] was begged and bribed by a coworker 26 [F] to cover for her vacation. from gonewildstories

A few days went by after Jessie left for her vacation and I realized that either I was very lucky, or her job was way easier than I thought! The first week customer service got a total of five calls, and they were very simple to handle. By Monday Jessie started sending me pictures, and she sent me at least one each workday. I got mostly the classic bathroom mirror selfie from their hotel room, but she also sent me the odd picture from the beach. For those ones she’d be pulling aside her bikini to flash her tits or her pussy while her man was busy.

When she finally got back to the office it was all I could do to act natural. She was wearing a tight grey button down shirt and a black skirt, and just the sight of her was driving me nuts! When she saw me she ran over and gave me a big hug.

My first bisexual experiences [MM]

I’d taught myself how to cum by humping my bed and I continued to masturbate that way just about every night until this one night the following summer, I was staying over at my friend’s house. I don’t even remember how it started but we ended up getting naked in his bed, I think because he said it would feel better. After getting each other horny by talking about hot girls we knew, he started jacking off. I then flipped over on my stomach & started humping the bed and he looks over at me & is like “Dude, what the fuck are you doing? I told him I was masturbating, & so he showed me how to do it properly. So we jacked off together, cumming at about the same time. We didn’t touch each other, but for some reason I kept feeling compelled to rub my bare feet on his bare feet. He didn’t seem to care. That happened every time we got the chance, then about a year later, the following summer, he was spending the night again, we were naked and masturbating in bed when he suddenly took things to another level. He suddenly rolled over on top of me and started grinding on me. This was new and a little scary but it felt so good! He was kissing my nipples and grinding his cock on my cock. Eventually he came on my chest, and then grabbed my cock and jerked me off until I came.

[MM] My first time with another man

This is a long story that happened a very long time ago in the late 80s. It is a story that some might find troubling, I myself have mixed feelings about the relationship. But with time comes clarity and with that clarity of time, I have come to accept that much of what transpired was very much by my own design.

I grew up in a pretty fucked up home environment. My parents were both drug addicts, cocaine mostly with some heroine mixed in just for kicks, and there was a lot of abuse and neglect during my formative years. Growing up in such an environment can have serious negative impacts on a person and I was no different. I was pretty much heading down the same path as my parents until I discovered the sport of wrestling in 8th grade.

I was a natural at grappling. I’m naturally athletic and I had a mean streak a mile long (a direct result of my Father’s approach to parenting). So wrestling gave me an outlet and a focus that I desperately needed. When I got to high school I went out for the team. I was the only freshman wrestling varsity at my weight class and before long I became one of the leaders on our team and earned a reputation regionally as a formidable wrestler.

My Sister Lizzy Part 3 [MF] [MM] [BDSM]

“Make love to me.”
I stepped up to her and began to undress her while looking deep into her eyes.
Starting with her top I lifted her arms and very slowly raised the shirt and removed it.
Leaning in for another kiss I undid her bra and she shook it off of her shoulders.
In front of me were the most wonderful breasts, as I said she had these little “A” cups with a chest that was almost flat and a pair of nipples that stood proud, like a pair of pencil erasers.
Lizzy loved her little titties and would look down with distaste to anyone who thought breasts make a woman and I loved her for that.
I spent a long while just teasing them to their full hardness.
Taking a lesson from Lizzy’s own playbook I went to my closet and took a wide black tie.

Stepping up to Lizzy I asked her “Do you trust me?”
“Yes” Was her answer.
I requested that she stand passive and not to touch me until I ask her.
Taking the tie I placed it around her eyes and tied it, blocking her vision.
I turned her away from me and began to trace my finger ever so gently across her spine and along the lines of her back.
As I did this you could see little shivers crawl up her back wherever my fingers had just traveled.

Beta (Femboy, M on M)

Beta

Nakia walked around campus, his hand interlocked with his girlfriend who joked beside him. He wore baggy clothing, his hair a soft bright red, his face girly though hidden well under a cap he wore, a beauty mark under his eye, a smile on his face. Lately he’d been getting closer to his girlfriend of a few months, having gotten into the college he wanted and being able to finally express himself since he’d been bullied in high school for how he was and how he acted. He found people really annoying but girls were rather friendly to him, and even when they found out his secret, they still seemed to support him and treat him well… his secret being that underneath the clothing he wore was a body that was a woman’s despite having no breasts and something between his legs that belonged to only a man. He found himself always conflicted with his body but it didn’t stop him from trying everything he could to still live a normal life and not stand out. His face twisted at the idea and his girlfriend poked his ribs causing him to chuckle carefully, almost giggling. Slowly they walked back to the girls dorm, Nakia and her talking excitedly for a movie that they wanted to see together before he gave her the usual kiss when he left her back at her room, going back to his own. He smiled as he laid down on his bed and thought of her before he heard the door open, looking over in annoyance as he took off his hat and laid it on the nightstand. There in the doorway was his roommate Tyler who stood a few inches taller, a strong face that could give a smile that would melt any woman’s heart, blonde hair combed neatly back, strong and toned, his arms reaching to lay down his backpack onto the floor before pushing it into the closet to his left. He looked over at Nakia’s glare and gave a sigh.

A sexy secret agent and her mysterious mission. [Seduction] [MF]

Sasha was a secret agent, trained by the government. She was a tall, blonde, 48-year-old curvy woman. She had soft, big and rounded breasts. Even though her fighting abilities were amazing, her body played an important part in defeating her male enemies. She seduced them with her incredible beauty, and distracted them. This time, she was on a mission to defeat and capture Alec Lightwood. He’s a professional fighter, and knows how to use a bow and arrow like no one else. This is the time to show her skills, this is the time to prove herself. Alec is a part of the opposing political party. The government is malignant, and trying to exterminate any competence for their next candidate. Alec was the son of the biggest competitor against the government, and therefore was the key to defeating his father. However, would Sasha be able to defeat him and capture him?