Mark was my first FWB. I had already been secretly experimenting on my own for a while. I would steal my aunt’s, cousin’s, and sister’s panties and wear them so I could see my ass in panties. It eventually transformed into wearing them, pretending to be a girl, and imagining what it would be like to have a boyfriend. But Mark didn’t know that. So when things began, it really escalated.

I met Mark in band. We played the same instrument. Then I found out we were both in football. We were assigned lockers next to one another. Everyday we had practice. And everyday we changed in the locker room next to each other. I hadn’t had a single thought about any of the guys around me. Just platonic straight bros. I still had my panty secret to myself.

Then one day Mark told me I had a girl’s ass. I was surprised obviously. Never had anyone told me something like that. I took it as a tease and didn’t mind any time he said that to me. But along came Andrew. Moved over to our block of lockers, the three of us quickly became friends. Mark decided to tell Andrew, that the joke of our lockers was that I had a girl’s ass. Andrew quickly agreed and joined in the teasing.

Mark and I had a lot of time hanging out together. We were typically early to school drop off by over an hour before school started. We began adventuring out around campus and even into the neighborhood next to us where there was a park to hang out at. I saw Mark’s cock for the first time there. We both needed to use the bathroom and we both went behind some trees to take a leak. I was done and pulled my pants up. I turned around and Mark was barely pulling up his. A black cock. Cut. Bigger than my cock.

Mark was in a fight at school. I saw it happen. It was too late for me to intervene but I did follow him to the bathroom when he ran inside. He was at the urinal with his shorts down. I walked up to him and asked if he was okay. Unfortunately, he had been kicked in the balls kind hard and I knew he was in pain. Mark told me that he didn’t know if his balls were okay. He was my best friend and I felt really bad for him. I could only imagine the pain. I volunteered to check for him. We had been in health science class together and had learned about checking ourselves for injury. So I looked at his cock and gently cusped his balls. Warm and soft. I asked him if he was in any pain. He said he was okay. Slowly I carefully felt the roundness of them. Complete and whole. Then I held his shaft. I had noticed it had grown a bit. A quick image of my ass in my aunt’s panties flashed in my brain. I shook it off and checked again for any bruising. He was okay.

In basketball the following summer. Myself, Mark, and Andrew were in basketball camp together. We found a bathroom with the lights off. In a stall Mark and I played a game of chicken. He was playfully humping me and I was pushing my ass back. We would do this a few seconds at a time. On the third return to the stall, Mark had the bright idea to have body contact as a dare. I took him up on it and he gently rubbed his hard cock against my bare ass. The image of me wearing panties flashing in my mind and feeling like a girl with a boyfriend. We eventually told Andrew what was going on in the stall when we told him to keep watch by the door. Andrew joined in. From there it blossomed into a full on love triangle.

Mark wasn’t as sensual as Andrew. But he was way more insatiable. Often going 2-3 times if we could. He would always grab my ass on bus rides. Even in the riskiest times I would feel his hands slip into my boxers to grab a handful of warm squishy cheek. One night he was literally on the phone with his girlfriend while giving it to me doggystyle.

Mark was the first to swipe some panties for me to wear. It was a surprise but a pleasant one. I was still wearing any panties I could get my hands on secretly and I had already wanted to do so for Mark and Andrew. Mark was also the first one to finger me. Teasing me from behind dry humping me with his shorts on. I felt his finger explore close to my hole and then slowly penetrate me. Mark also was the first to lick my ass. It was a wonderful idea to sit on his face. Something he saw on the hub. Fantastic.

Mark had his own way of role play with me. He liked for me to pretend to be asleep. He would explore my body. Kiss my skin and play with my ass. Then I would wake up from my fake slumber and give him a blowjob. Since he liked going multiple times, I could swallow his first load, and then he would lick my ass until he got hard again. We never talked about boyfriend girlfriend scenarios. Never any mention of him imagining me being his girlfriend or any one else. Just pure sexual satisfaction. For both of us.

Our last hook up was at my place. Regularly on Sundays he would come over before work for a couple of hours. I was always alone at that time. Mark had to change his work schedule to accommodate his college class schedule and this was his last Sunday. I was headed off to college soon and I had my last time with Andrew just a few days before. We knew that it would be our last chance together and had several sexting sessions leading up to it over the week. He wanted to shower together. We had showered together on away band trips when we were lucky enough to room together. I wasn’t shy to see Mark in full light and in boy mode. I gave him a blowjob in the shower until he emptied his first load in my mouth. Then he washed up and left me to shave my body smooth and prepare for him. In a bag on the sink he had picked out an outfit for me to wear. Clothes meant for a garage sale that he saved for me. Pink shirt and a frilly skirt that was just to my knees. I mentioned in another story that Andrew preferred when I wore full coverage panties. Bikinis, boy shorts, cheeky panties, etc. Mark liked more revealing panties. Thongs especially. I even had a makeshift thong we made by tying some strips of an old shirt together. On this night I had a thong that I took from my girlfriend’s older sister. She was a bombshell and I had my share of glimpses at her panties peeking out. She had a drawer full. Left in her dresser drawer after she’d moved in with her boyfriend. I knew I had to have them for this moment with Mark. Out of my costume box, I had two wigs that I was pretending to be saving for my girlfriend for Halloween. Mark’s favorite was the red one.

In my full outfit we fulfilled Mark’s second wish. He was on my bed in his boxers. He wanted me to give him a full show of my body and tease him until he was rock hard again for the second round. Again I was not shy about this. Mark’s sexual peak was unknown. Over the years together sneaking around, we tried anything we could think of. Since we were two bros hooking up in secret, might as well go all out. I sat on his lap and rubbed my body against his. I felt so feminine showing off my body dressed up on top of him. When I gave him a bent over view reverse cowgirl, he spanked me. I loved feeling that tingle on my cheeks. He was hard and ready for a blowjob. Although he was definitely longer than Andrew, he wasn’t as thick. Deep throating him was no problem.

On the list we made was for me to lay prone and let him play with my ass. I had made a routine to keep a nice round soft ass. I came up with the idea when I noticed some razor burn one day examining myself in a new g string I swiped. A while into my skin routine, I guess I was looking really good because Mark and Andrew started paying considerable attention to my ass. As I was playing prone, Mark kissed my ass and legs. He shoved his face between my cheeks. Staying so long sometimes I wondered if he was even breathing. I pushed my hips back against him feeling his tongue pressing into my hole. I moan quietly. Andrew wasn’t often in favor of playing with my clit. I didn’t mind it at all. I just care about being fucked. But Mark really enjoyed kissing it from behind. I loved to feel him kiss my ass up and down. Then to my swollen limp clit and back up again.

Next on the list of our final hookup, was any position we could think of. In our texts, we described several different ones. First up was reverse cowgirl Since Mark was longer than Andrew, this was no problem. I could ride Mark hard and fast with plenty of his shaft inside me. I can still hear the clap of my cheeks on his cock when I think about it. Mark spanking and squeezing my ass. I felt like a real girl riding dick. Next was a personal favorite of mine, missionary. I really really loved looking up at Mark and Andrew as they got their needs met inside my hole. I kept my skirt on. Mark like keeping my clothes on, he lifted it up to get a full view. I would always get hard in this position and Mark didn’t mind at all if I jerked on my girl cock. In and out he went. I savored every second and every inch. Mark pounded for what seemed like several minutes and only a few seconds at the same time. Just enough but not long enough. I could tell Mark was about to cum. So the last position was in order as we planned. I bent over the edge of the bed and let Mark go to town on me from behind. Loud clapping. Uncontrollable moaning. Electric tingling as he pressed against that magic spot deep inside me. He grabs my hips and thrusts one final time inside me. Emptying the last bit of cum he would have inside me ever again. As he throbbed in me I begged him to slowly keep stroking. And on the third or fourth stroke I shot out my own cum all over the floor underneath us.

Mark laid on top of me. Inside me. For a while as we both caught our breath. I felt him going limp inside me but still firm enough to stay inside. I circle my hips for him a bit and we make out. Then he gets up and goes to the bathroom to get ready for work. I lay there tingling all over. Replaying the last hour in my mind many times. I had my favorite moments already. Flashes of my girl cock flipping around while Mark’s cock was thrusting inside me. Mark returned to the room for his final request. Watch his cum fall out of me and a final blowjob in his work slacks. I bent over on the bed and Mark fingered me. My boy mind completely gone. Replaced by a sissy. Then I gently pushed his seed out and he got a full view of me. He was hard again. I sucked his cock out of his pants zipper. Then I tasted whatever was left of his cum in my mouth. Surprisingly only lasting a few minutes after going two times. He zipped up his pants, we talked about when I would leave and then he left for work.

I never saw him again after that day. For years I touched myself and daydreamt about him and Andrew while I dressed up. Mark always fucked me so good. Just pure sexual satisfaction for both of us. Andrew was more sensual. I would roleplay as his crush from school and he would fuck me as if I was her. Two different rides. One incredible experience.