[mff] True tellings of my sexual awakening Part3

[Part 1 Here](https://www.reddit.com/r/eroticliterature/comments/88w9u6/mff_true_tellings_of_my_sexual_awakening_part1/)
[Part 2 Here](https://www.reddit.com/r/eroticliterature/comments/895nl5/mff_true_tellings_of_my_sexual_awakening_part2/)

The discovery of Kirsten’s scent mixed with the early stages of crossdressing was the best sexual thing I’ve ever encountered. The euphoria I got from inhaling her scent and then feeling myself become a girl with a cock lit a fire within me. I started watching more and more anal porn and liked it, because I could better imagine what was happening on the screen happen to me. When I was 15 I had a girlfriend but she never knew about my secret fun at Kirsten’s. I got my first job at Kirsten’s dad’s office and opened a bank account in my own name which came in handy. I loved watching bukkake and anal porn because I always imagined myself on my knees getting sprayed by cum or on all fours getting fucked in the ass. I wanted to feel that for myself, but was too scared to do anything with a real guy since I was in a relationship. The first time I did anything with my ass was, again, at Kirsten’s house. Nobody was home and I did my usual panty sniffing and cross dressing, but this time I took it a step further. I looked through Tori’s leftover clothes she didn’t take with her to college and put on a miniskirt, her high heels, and then a bra and tight fitting shirt. I took pairs of her socks and stuffed them so that I had boobs. I looked HOT. I was a girl. I couldn’t stop thinking about all of the anal porn I had watched. I decided to try something out. I bent over the counter, pulled up the skirt, pulled the thong to the side, and admired my tight pink asshole. It looked just like a girl’s since my thong was covering my balls. I loved the way I looked. One hand gripped my butt cheek and the other went to my mouth. I covered a finger in spit and slid it across my hole. GOD it felt good. It felt really good. I spit on my finger more until it was wet and slippery down there. I slowly penetrated my asshole. WOW did it feel great! It hurt slightly, but it felt amazing. I played with my ass for a good while with just one finger and decided to call it quits for the day. I looked up anal sex prep tips and found writings of using enemas. I didn’t have an enema, so I improvised. I found a big syringe and filled it with water – it could hold three ounces. I slowly pushed the tip into my butthole and pushed down the plunger. I did this over and over until I began evacuating. I then found a small travel shampoo bottle with a round, smooth lid and started playing with my ass some more. I managed to get the bottle in my butt but it HURT so bad! I took it out and then felt the cool air against the inside walls of my asshole. I gaped for the first time. I just lay there on my stomach with my ass arched in the air and asshole gaping on its own. I was a young 15 year old boy who was discovering a world of pleasure. This became a regular thing for me. I loved feeling like a girl in the videos.

I started playing with my ass all the time. One thing that intrigued me were tampons. Kirsten and Tori always had boxes and boxes of them. Sometimes, I would go in their bathroom, spit on a tampon, and insert it into my butthole. I’d then sniff for panties, jerk off, and then get rid of the evidence. This became a regular thing and since they had so many boxes of them I thought they wouldn’t notice. Sometimes, I would put one tampon in then another and another so it filled me up. Then I would get that syringe and squirt a little bit of water in there and oh my goodness did I feel full! When I was using tampons, I felt like the girl.

I decided that I wanted to see what all the hype was about with anal. I started looking online at dildos and found one on adamandeve.com that was only $20, discrete shipping, and looked just like my own dick. I will admit that I got rock hard while looking at all of these cocks I could play with. I bought it and when it arrived I was so anxious to open it. I had to play outside til the mail came and hid it from my mom. I took it to my room immediately and opened the packaging admiring this beautiful cock before my eyes. I was touching and holding a COCK for the first time that wasn’t my own. I had seen other guys hard dicks before but never touched one. It felt so squishy and kind of sticky. I spit on it and stroked it and was eager to fuck myself with it. I looked up “how to anal sex” again and read up on all the tips. I discovered that prostate play was a thing and decided to try it with my fingers. It took a while for me to figure out what I was supposed to be looking for in there and I gave up a few times, but one day I found it and that was the day I took a dildo in my ass for the first time.

I prepped by getting in the shower, shaving my balls, pubes, and asshole. It took me a while to get used to the dildo. I started with one finger, then two fingers, and worked my way up to 3. It was starting to hurt around 3 so I took a break and went back to 1. I must have spent an hour or so playing with my asshole with my fingers until I was ready to take that dick. I needed to lube it up – but how? I didn’t have actual lube… I thought of something. In deepthroat videos they always produce a lot of spit – why not just do that? I went back to 3 fingers in my asshole trying to find my prostate and then started sucking on the dildo. Oh my god, did that make me hard! I kept sucking away on it, going deeper and deeper each time, pretending that it was a real dick with balls flapping against my chin. I wanted to be the girl in those bukkake videos getting face fucked over and over. I wanted multiple loads of cum across my face, in my eyes, in my mouth, everywhere. I kept pushing and pushing this dildo forcing it down my throat until my eyes started watering and I gagged – all while having three fingers playing in my shaved asshole. Taking it out, seeing it covered in my spit, I knew it was time. I put the suction cup down on the bottom of the bathtub and positioned it. I slowly lowered myself until the head was aligned. I took my hand and put it in my mouth so I could get all the spit I could need and then spread it on my virgin hole. I put the head of it on my ass and just lowered myself onto it. I felt the head of it enter and kind of suck up into it. It wasn’t that bad! It wasn’t as big as I thought it would be. I kept lowering myself down, this time picturing Tori squatting on a cock wearing those high heels I liked to wear. I wanted to be her. I slowly went further and further until I felt it starting to stretch my asshole more and more. I stopped then went back up. Then back down, trying to go further. I closed my eyes and kept them shut picturing Tori riding this dick. Oh how I wanted to be her! I kept going further and further and then WOAH! I let out a moan out of nowhere! My body got tingly – almost like that first time when I was rubbing at my briefs watching a girl masturbate on the TV. I knew I had hit my prostate correctly. Even though it slightly hurt my asshole to go that far in, it felt amazing. I kept doing that for a while and then gave myself a break. I then positioned myself my knees and one elbow with the other arm equipped with the cock. I began penetrating myself again after I gagged on it a few times for lube. Fuck this feels good. I took it out and felt myself gape again – I knew I was – I could feel it. Tori and Kirsten had a small fogproof shower mirror in their shower. I suction cupped it to the wall so I could see this cock sliding in and out of my pink asshole. I gripped my cheeks and spread my ass when I took out the cock to see a glorious, fresh gape. Tori’s gape. I went back to fucking myself until my knees hurt. I was having so much fun I didn’t realize how much time had gone by until I heard a knock at the door. “Are you alright in there?” shit it’s Kirsten. “Uhhh yeah I’m almost done!!” I quickly took the dildo and washed it off. I equipped a towel and hid the dildo in the towel and under my clothes to my room at their house. I got dressed and acted like nothing was unusual. I loved being the girl.

One day, while at Kirsten’s, I went into the bathroom and started rummaging in the hamper. Oh crap. Oooohhhhh crap!!!! I’m caught. I know it. FUCK! I thought it was all over… The thong that I had been playing with the day before wasn’t where I left it in the pile of clothes. I would always make mental note of where they were so that I could put them back into place to not get caught. But the day before I put Kirsten’s red and black stretchy spandex/lycra thong back where I found it and it was in a different spot. It was in a very different spot. Instead of being wadded up/thrown in there halfway down and on the left underneath the yellow shirt, like I found it initially, it was on the very top of the pile, in the very front of the hamper, folded neatly into a little square. She knows… I’m screwed. My life is over. Blahblah. I opened the bathroom door and she was standing there with a look I had never seen before. She looked eager and excited but nervous at the same time. She said “everything ok?” I said yes. She said “Did you see what I left you?” I froze. I couldn’t think of what to say. I just stared blankly at her. She moved past me into the bathroom and looked at the hamper and without saying anything reached into the side of her pants and pulled up a purple thong above her jeans and showed it to me followed by “whoops” then shut the door. I stood there and could hear her peeing and she told me to go downstairs. I did. I went to the spot we hung out at and she came down there and acted like nothing happened. It was just us in the house. Her dad was in the garage like usual, her mom was out doing something, and Tori was at college. She asked if I needed to go to the bathroom again and I said “no I’m ok” and she replied (and I’ll never forget this moment), “You need to go to the bathroom.” I anxiously said okaaaaay? And went straight up. I closed the outside door and my heart was pounding. I went in and looked in the hamper. Instead of the black and red thong being there neatly folded, it was the purple one she JUST showed me! I picked it up and it was soaking wet like it was submerged underwater, except it was slimy. There was white creamy stuff on it. Oh my GOD! She did not just do that!!!! I smelled them, I slurped up her juices like it was water in the desert. I was tasting her pussy fresh from the source! It was tangy, creamy, kind of salty, and had an amazing aftertaste. Kind of like how alcohol stays on your breath – I could taste her pussy when I exhaled. I jacked off so fucking hard. I had never shot cum before that moment like the guys in the videos, but when I came it hit the bottom of the toilet seat and splattered. Two powerful, fierce shots. There was so much cum afterwards. I heard a giggle from outside the door. I didn’t care. I was in so much ecstasy. I cleaned up and flushed and heard her run off. We were both 16 at the time. I have never tasted pussy as good as hers on that day. We never spoke of it again, but she knew I loved her panties and would often take them off and leave them on the top of the pile of dirty clothes for me. She’d get home from band practice all hot and sweaty, go take a shower, and I’d dart in right after and always find a pair of strongly scented panties presented for me. This lasted for about 7 months and was the most fun period of my life ever.

While the other things were chronological, this just popped into my head. Over time, I discovered my foot fetish. It was weird, because when I was younger I used to think feet were gross. They smelled, they felt clammy, they were just weird. Oddly enough, in highschool when girls would wear flip flops I loved staring at their toes. I didn’t know why since I didn’t like feet. It wasn’t until I was about 19 that I came to admire and love girls feet. There was no rhyme or reason. They had to be pretty feet, though. It was actually a prereq for any girl I dated – she had to have pretty feet. Now that I’m older, I’m much more open about my foot fetish and don’t look at it as weird anymore. I love girls feet and can worship them all day every day. My fantasy, which will be revealed soon, involves feet, cum, and me being the girl.

Source: reddit.com/r/eroticliterature/comments/8amk6f/mff_true_tellings_of_my_sexual_awakening_part3

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