(MM) Jock’s first gay sex with Fem Boy

My senior year, I had a journalism class. I was aiming to be a sports reporter since I had a career-ending injury the year before while playing football for the school. Halfway into the semester, we were assigned to investigate and publish a story with a randomly assigned partner from the class. I was assigned, Sam.

I didn’t know Sam, but he was very friendly. Lots of girls in the class loved him and they hung out with him in the evenings. He was also very gay, often wearing Pride clothing, and known for all his rainbow laptop stickers.

At the time, I had no interest in males. I dated cheerleaders, normal jock stuff. But everything changed after my injury. My friends on the team drifted away from me, and so did the girls who liked being around the football team. I was very lonely, and (looking back) very depressed.

I arranged to meet Sam at his on-campus apartment to discuss the class project. When I arrived, his roommate was leaving out the front door. “Hey, I’m here for Sam; I’m in his journalism class.” He didn’t even look at me, obviously in a rush, when he said, “Head on in, I’m late for work – I think he’s in his room, he’s expecting you”. He rushed down the stairs and I entered the left-open front door. I headed through their kitchen/dining space to the rear of the apartment where I thought the bedrooms were, and found a wooden door with “SAM” cut out in big letters, and taped onto it – along with cut-out photos of him with a ton of different friends and family members.

His door was slightly open, and since his roommate said he was expecting me, I swung it open. At the same time I realized the handle was actually locked, and he just hadn’t closed the door all the to successfully accomplish privacy. I found him on a bed pushed up against the wall of the room, he was laid across his bed, several feet away from his laptop, obviously on a webcam session. Immediately after, I noticed his clothing. He was wearing a blonde wig which covered his usual short dark hair, and what looked like a tank top and shorts at first was actually a white bra and panty set, connected by garter straps to white stockings.

Our eyes met in shock and embarrassment, for both of us. He obviously thought his door was locked, and I had felt horrible that I did not give him verbal announcement to my presence. In all the commotion, I had only barely noticed his flaccid dick, shaved smooth, hanging out the side of his white lace panties.

He let out a shout and mumble, not saying anything in particular. And I averted my eyes, apologized profusely; blaming his roommate for the permission to enter, and I quickly ran out of his room, the apartment, and back to my car.

I started the car, but sat still. Feeling so awkward and guilty for catching him in a very intimate moment. I must have sat there for a while before finally my phone vibrated in my pocket. Someone was calling, but I let it buzz away on my lap. The vibrations were strangely pleasant, as I noticed a growing stiffness in my cock.

I snapped myself out of my stupor, and answered. “I’m so sorry about that!” Sam pleaded. “I thought I had closed my door, but I should have checked it before I… well…” As he struggled to finish his thought, I also apologized again in circles, assuring him it was fine. “Well, I’m … dressed now. Feel free to come back in and we can get started, I lost track of time but I *am* ready for you”. To me, that sounded good. He was “ready for me”. The stiffness came back.

As I left my car, and headed back to his door, I questioned my dick’s response to what I had seen and heard. I knew Sam as a classmate, but never felt this way about him. But seeing him dressed in a feminine way had done something to me – awakened a feeling in me that I’ve only had seeing women in their underwear. Maybe I was just attracted to underwear.

He was waiting at his front door. Trying to laugh off what had happened. Gratefully he was wearing a university t-shirt and nike running shorts now. Much easier to focus, for me. I followed him in and sat at a dining table where he had notes and files waiting for us. We spent ten minutes pretending to focused on the project, before an awkward silence ruined our flow.

“Can I explain what you saw?” Sam said. I assured him that his private life was none of my business and I did not expect him to share such things. “Well, thank you, but I want to go over it, you’re now the only person who has any idea what I do”. I closed my laptop, and paid him the courtesy of my undivided attention. “I have been ‘dressing up’ for a few months now. It started as just a curiosity for myself, but then I learned that some guys really like looking and watching – so I have an online account and do live shows as a way to make some extra money”. My head was spinning. In a matter of 30 minutes, he had gone from my classmate partner, to my webcamming gay dress-up porn performer.

As he finished explaining, it was then that I noticed his mascara and eye shadow that he had been wearing. Trying to be kind and supportive, I said, more honestly than I expected, “Well, you looked great to me”. My eyes went wide as I realized what I had said. “Really?” Sam said, obviously flattered. “Are you into guys?” he continued, cautiously. “I… haven’t before” I stammered, and then in a moment of pure honesty and truth, I continued: “But I guess I might be attracted to anyone who is feminine. I love women in lingerie, and seeing you, I had the same arousal. If anything, this accident has given me plenty to think about”. I smiled at him, before realizing what I had just revealed.

What was happening to me!? I’ve never spoken to this boy before, and here I was in his apartment, working out my own sexuality in front of an out gay person. His cheeks were flushed red, but he was appearing more relaxed instead of upright and polite. He crossed his smooth legs, and his short running-shorts revealed his lean thighs and just the bottom of his hairless ass.

“Well, I take that as a huge compliment. Especially from a football player! I am a proud gay man, but I do enjoy presenting feminine, and I do get off on dressing sexy”. Get off? Looks like I wasn’t the only one slipping some hidden truths. He remained relaxed and smiling coyly, whereas my stomach was in knots. I wanted to tell him everything I was feeling, but also wanted to run away from my feelings. But I had been so lonely lately, and Sam was the first pleasant and honest conversation I’ve head in weeks. And I was realizing quickly, that his smile, beautiful eyes, and hard little body were making parts of me feel alive, on fire.

Sam leaned forward, obviously I had been quiet for a while. He was obviously much braver than I, because the next thing he said made me gasp: “So, you like what you saw?” His eyes sparkled, in a way that no other had ever looked at me before. Sam had me wrapped around his finger, as he reached his hand over and place it on my hand.

Looking back, I wish I had said something smooth or confident; but instead, with my mouth hanging open in disbelief, I nodded and said, “Yeah, it was so hot”. Again, shocked and surprised by my candid answers. He leaned forward further, his teeth showing as he grinned, and asked, “Well, I’ve always thought you’re pretty hot too. My roommate is gone for the evening. Would you like to see a bit more?”

I think I surprised him by how quickly I responded with an emphatic “Yes”. He grabbed my hand, and walked me back in the direction of his bedroom. I tensed up again as I crossed the threshold of his bedroom. His webcam streaming set-up was still intact, I worried he might want me to join him for an online show! I assuringly walked to his bed before he grabbed my hips, and motioned me to an arm chair off-camera, on the other side of the room. Sam assured me saying, “I was going to go live again, so if you would like a front-row view, and enjoy, I would love your company”. Relieved, I sat down and relaxed. I looked around his room, lots of white blankets, faux-fur rugs, and white furniture. He was rummaging through his closet, looked to me and asked, “I have QUITE a lingerie collection. What’s your favorite style?” This was quickly becoming heaven. After a long ‘um’, I stuttered, “Well, I love black. It makes a good girl look like a sexy vixen … or guy I mean”. Embarrassed that I referred to lingerie as just for biological females. He gave an audible laugh, and asked “How does a sheer black Babydoll and sheer panties sound?” I nodded vigorously, I was at least a foot taller and much more built than Sam, but he could have me begging on my knees if he wanted to.

He took off his t-shirt and shorts, and stood naked in the middle of the room as he gathered the clothing and accessories. He had such a nice body, he was lean, and toned, but it was his smooth hairless crotch and body that was causing my jeans to be visibly uncomfortable. He saw me shifting and adjusting my pants, trying desperately to get comfortable. He kneeled before me and while pointing to the front of my pants asked, “May I?” Another eager nod showed affirmative. Sam unbuckled my belt, and loosened my jeans before tugging my jeans down, leaving me in my Nike boxer briefs. “Mmmm, love those” Sam confirmed. Before he stood back up and began to dress. He wore the black babydoll, panties, and matching black lace stockings. He accessorized with a gold necklace, earrings, and bracelets. Sam had become one of the sexiest, most feminine things I had ever seen. He turned to me again and asked, “Do you have a preferred hair color?” He pointed to 3 wigs he had on a shelf in his wardrobe: Red, Blonde, and Dark Brunette. “The dark brown matches yours, I like yours, so that one” I admitted. He smiled again, in his coy way, but this time it was even more flattered and appreciative.

He didn’t talk to me again before he knelt on his bed, started his camera, and began a broadcast. It had become my own private room at a strip club, as he moved his body to music, sneaking peaks of his ass and dick to his audience. I heard bell chimes over the computer, he always said “Thank you” in his sexiest voice, so I assumed it was money he was being given as a result.

He looked over to me several times, assuringly. As he faced his smooth ass to the camera, he nodded to me and mouthed, “Take it off”, so his audience wouldn’t hear. I took a breath, smiled, and peeled off my long sleeve football team-issued shirt. He opened his mouth and made a gasping noise, and giggled. I rested back down on my seat, as I watched him sit back on his bed. Speaking to his webcam, he said “Ok you guys, I am SO horny. I don’t want to put it off any longer. I need to cum!” This caught me off guard, I didn’t know I would also get to witness his happy ending.

He spread his legs and pulled his smooth erection from his panties, and started slowly stroking his cock. He closed his eyes and starting moaning sweetly. I felt pulsing in my own cock, but didn’t want to get caught jerking off, so I discreetly tugged at my dick through my underwear. But he opened his eyes occasionally, and each time he did, he would look me in the eyes and smile. He was turning me on already, but his gaze and expression pointed towards me had me feeling electricity from my eyes down to my toes. I have never had a harder erection – I pulled my dick out of briefs and started stroking to match his pace, staring him right back in the eyes. As I did this, he threw his head back and groaned as he shot a creamy load all over the floor, where a towel had been strategically laid to catch his cum. The chimes on the computer were constant, his fans were very appreciative, as was I. He thanked his audience again, gathered his breath, and bid them farewell before he ended the stream, and closed his laptop.

He looked over to me, seemingly looking for approval of his ‘performance’. I stopped stroking, but kept my hand on my cock, mostly out of shyness, and said, “Sam, I … just … that was … “. Sam laughed, and said, “I’ve never had a boy speechless for me before!” I looked down shyly before returning to his gaze. His dick had softened, and he tucked into his black sheer panties again. He kneeled up on his bed, still wearing his wig, babydoll, and stockings. With a low whisper, he asked “Would you like to join me on the bed?” I stood immediately, and sat on the end of his bed beside him. He crawled to me, and straddled my lap, I instinctively put my arms around his waist as he put his arms around my neck. “Can I kiss you?” he asked with a breathy desperation. I nervously nodded, and he gave the softest closed mouth kiss on my lips. I closed my eyes, and felt hot body pressed against my chest as our kiss began to open, allowing our tongues to meet. He started rocking his hips in such a way that pressed against my aching cock. While I was so much enjoying the romantic experience, I was equally as desperate to experience an explosive orgasm of my own. I took my hands from his back, and tugged down my Nikes. His eyes shot open, and that adorably-wicked smile crept across his lips. I kicked them away, and before I could return to the position. He stood up and said, “My turn”. He pulled down his impossibly-sexy black panties, and pulled off his black baby doll. He stood before me in his bare skin, gold jewelry, long brown wig, stockings, and the best makeup job I’d ever seen. “Fuck me”, I blurted out in a moment of carnal shock and honesty. But with a wink, he responded, “No, YOU… fuck … ME”. He sauntered over to the middle of the bed, and got on his hands and knees, his bare ass presented in the air. I had enjoyed doggy style with girls before, but never another man. But seeing his limp cock hanging down, and a gaping pink asshole ready and waiting, I didn’t hesitate. I stood behind him, taking a second to massage his cheeks and balls. I could feel him shiver at my touch. He motioned to a bottle of lube on his nightstand by a vibrator, and I slathered it on – perhaps too much as it also dripped onto the town which caught his cum earlier. Perhaps he could sense my nerves, as Sam said, “Don’t worry, I’m ready, I want you”. This feminine beauty was my whole world at this point. My confidence soared as I felt true attraction for the first time in many many months. I pressed the head of my throbbing dick to his ass, which readily opened for my presence. He gasped and rolled his eyes back as I continued sliding slowly into his perfect ass. I stopped and waited to hear if he was okay, but upon stopping, he brushed aside the long hair of his wig and said, “Don’t stop daddy, give me your cum, fill my little ass with your cock”.

Never before in my life had I felt more masculine, more capable, or more desired than I did when I had my cock inside this beautiful boy. I fucked him fast, grabbing and kneading his ass, and basked in his moans and stuttered breaths. As my balls slapped against his, I could feel his cock getting hard again. Those sexy words, sounds, and the erection I was causing him combined to send my over the edge. With a final deep thrust, I poured a huge load into my lover’s warm smooth ass. As I emptied cum into him, he looked back smiling, with tears in his eyes. I was afraid I had hurt him, but he kneeled before me, took me in his arms and proclaimed, “No one knows how feminine I am, expect for strangers on the internet. You made me feel loved and adored and sexy while I was being my true self. Thank you for helping me accomplish that!” A pang of emotion hit me too, as I responded “Thank YOU, Sam. This was not what I expected for a partner-assignment, but it turned out to be one of the happiest and most honest days of my life”. He took my face in my hands and kissed me deeply. I kissed him with a greater desire than I had ever shared with another.

As an epilogue, of sorts. We became official boyfriends after a few proper dates. Haha. We don’t know what the future holds with our careers, but its been a joyously happen time for both of us. I am now an “out” Pansexual man, realizing my attraction to all women, men, and non-binary feminine people. Thanks for bearing with me through a long story.

Source: reddit.com/r/sexystories/comments/l0xmzz/mm_jocks_first_gay_sex_with_fem_boy