Part 1 [here](https://www.reddit.com/r/gonewildstories/comments/8ubl4l/mm_losing_my_virginity_story_of_my_first_summer/)
Shortly after Bill and I finished on the couch we put our shorts back on and went over to eat some of the pizza. We talked a bit, mostly about work and acquaintances that we both knew. We each ate a couple of slices of pizza and sat back down on the couch, again talking and watching TV.
After a bit I started to slide over on the couch towards him. I guess he noticed I was doing that and he slid towards me a bit, eventually we were sitting side by side touching. I placed my hand on his leg, down towards his knee. My heart was beating so hard I felt like it was going to jump out of my chest! I have no doubt he heard how hard it was beating as he placed his hand on my thigh and told me I had nothing to be scared of and I should calm down. He gently kissed the top of my head as I laid my head down on his shoulder.
As we were watching TV I started slowly rubbing his leg – working my way further up his leg with every few rubs. He had his arm around me and was rubbing my shoulder. Eventually I made it to the cuff of his shorts. He was still looking up, watching the show so I made my move. I moved my hand up his thigh a good few inches – my hand was all the way inside his shorts now! His shorts were pretty long and I could feel that I was close to the head of his cock. My heart was beating even faster now. I was as nervous as I could be as I moved my hand up a bit further, looking up at him for approval when suddenly he took his other hand and gently pushed my hand up to his cock! It’s finally happening! He looked down at me and nodded his head as he slunked down in his couch, giving me some more room to work.
His cock was hard and massive – I could barely get my hand around it. I felt the cold metal of his prince albert piercing and rubbed the tip of his cock feeling on the piercing and feeling his foreskin. I peeled back his foreskin and the head of his dick was soft and lubed with his precum. It felt so good. He pulled me closer with his arm as I started stroking his cock. He reached for the remote and told me he was going to start a special movie. I was so preoccupied that I didn’t care what he was going to do.
He fumbled with the remote and realized he needed to change the disc. I didn’t want to let him get up but he started moving around so I let him. We both stood up and I told him this might be easier if we both take our shorts off again – he agreed and we both slipped off our shorts and threw them into the kitchen. It was the first time I had really looked at his body in a lustful way. He was taller than I was, at least 6’2″ and was well built. Muscular with just a twinge of fat on him. His cock stood proud at attention, twitching slightly as he moved. He walked over to the DVD player and swapped out the disc. I didn’t see what he put in but I really wasn’t looking at that. He went back to the couch and sat down and I followed – sitting very close to him with my head on his shoulder again. He put his arm around me and pulled me in tight.
My hand immediately went to his hard cock, pulling back his foreskin and looking at the head of his large member. The knob of the piercing glistened with his pre-cum – as did the head of his dick. I started stroking his hard cock with my hand, I couldn’t believe what I was doing!! I was so young and all this had been forbidden from me due to my strict upbringing but I loved every moment of it.
I stroked him for a while, maybe 5 minutes when he spoke up and told me to make sure I watched the movie. I wasn’t sure why he said this but it soon became clear. The movie started pretty innocently, there was a cute short haired girl with perky breasts flirting with an older bald man. The older man looked somewhat like Bill. I don’t remember the exact plot but I do remember the girl had a cute pink nightgown with matching panties. And I will never forget what happened next in the video.
As I’m stroking his cock, still nice and hard for me, the male in the video starts stripping. The girl comments and starts playing with his cock, stroking and sucking it, not unlike what I’m doing right now. But then she tells the guy she has a surprise for him – he asks what it is and says that she should show him instead. With that she lifts up her nightgown and pulls her panties down and she has a dick!! Not a big one mind you but she’s a trans, a shemale! I must have audibly gasped or stopped stroking his dick because Bill asked if I was ok. I told him I was, and that I was very excited to see the rest of this. He told me to pay close attention because there would be a quiz at the end.
The rest of the video went off as you’d expect – the guy acts surprised by the cock but winds up sucking on it and loving every minute, finally the video finishes with him anally brutalizing the girl – his cock barely fits inside her and he fills her full of cum. The film wasn’t long, maybe 15 minutes, but when it was done Bill asked if I liked it. At this point we were both sitting on the couch, cocks hard. I hadn’t been touching him for a while but I told him I liked it a lot – I had seen some trans porn and I was really getting into it. He asked if I wanted to do what they did in the video. I told him I wasn’t sure – who was I supposed to be? He responded by getting up and taking me by the hand towards his bedroom – “Why don’t you look on the bed and tell me what you think?” Bill quipped.
He pointed towards his bedroom and told me that he’d be in shortly. I opened the door to find the lights dimmed and some candles already burning. On the bed, very nicely laid out, was a hot pink nightshirt and panties! Next to it was a pair of thigh high pantyhose, also in bright pink. I was so excited! He wanted me to dress up for him again! I quickly started putting on the clothes, starting with the pantyhose. I then slipped on the panties – they were a cute g-string cut – my cock fit neatly inside of them and they felt amazing! As I was slipping on the nightgown everything Bill and I had talked about and had done hit me like a ton of bricks. I quickly remembered the video – he wanted me to be the girl! He had been preparing me for this the whole time – the outfit I had to wear to eat the other day, slipping his fingers in my asshole and rimming me, not letting me play with his cock until this point – he was buttering me up to fuck me!
I didn’t know how to feel – part of me was so happy to be dressed like this – I felt cute and wanted. Another part of me was scared to death – I had seen his cock, how was I going to fit that thing inside me? At this point I was so horny and ready that I was willing to try. I finished putting the nightgown on and I opened the door and sheepishly told Bill I was ready. He was standing right by the door waiting on me. He walked in and put his hands on my hips – pushing me away slightly so that he could look me up and down. I felt wanted but I was also scared and embarrassed. Bill continued to look me up and down at arms length – I could tell he was impressed! His cock seemed to get harder and his breathing quickened.
“How do you like your outfit?” Bill asked?
“It’s cute! I guess I know which part of the movie you want me to play though” I replied.
“Is that ok? You said you’ve been wanting to take care of my cock and this is what i want” he said with a grin, moving his hand to his hard penis and pulling back the foreskin.
“This should tell you if I’m ok with it” I said back as I started to kneel down – his piercing and cock head staring me in the face. I parted my lips and began to kiss the head of his penis. It was salty and wet, moist with precum. I looked up at him, trying to give him my best blow job doe eyes. He looked down and smiled.
“I like what I see down there, keep going baby” he said with a big smile on his face.
That was all I needed. I immediately put the whole of his head in my mouth, sucking on it with all my might. It was a bit awkward – I had never really sucked on a cock before – just fondled one or two in my teen and pre-teen years. Honestly it didn’t start well – I was having trouble keeping his foreskin back and out of the way and the piercing kept hitting my teeth. After a few minutes though I really hit my stride. He was moaning and enjoying it quite a bit. I was able to get about half his length inside my mouth and I was gently stroking the rest. My legs were starting to hurt so I took his shaft out of my mouth and told him to lie down on the bed. He complied and I went to the bed with him.
His cock was standing at attention and I hungrily laid down between his legs and took his head and shaft into my mouth – it was easier to get it deeper this time – thanks in part to relaxing my throat and the new position on the bed. I was doing my best, taking his girth in and out of my mouth, tonguing his foreskin and head and stroking his shaft. I could tell he liked it, he was moaning quite a bit and making lots of pre-cum. I’m sure it wasn’t glamorous – there was lots of spit and his prince albert would hit my teeth every now and then but I got pretty good. I would bite and tongue on the piercing – he loudly moaned each time I did. After a little while he started humping my face. I hoped this meant he was close to cumming – I wanted to taste him so badly! Sure enough it was only about a minute or two later when he tapped my head and told me he was about to cum.
“You might want to stop sucking unless you want a mouth full” Bill moaned.
I waved him off with my hand. I had worked too hard not to taste him now. I started sucking harder, taking him in faster and stroking faster – I could tell he was close. His breathing quickened and I could feel his cock shuddering and his hips bucking as he started to cum. The first shot took me by surprise, hitting the back of my throat when I wasn’t quite ready. I brought my lips back to the end of his shaft and pursed them around his head – drawing his foreskin back with my tongue. He continued to cum, for what seemed like ages but was likely only 5 seconds or so. Still, it was enough to fill my mouth. He let out a loud moan as his seed filled my open mouth. I swallowed as much as I could. It tasted good, slightly sweet, but like seawater with a hint of bleach. He reached down with his hand, stroking his dick to get out everything he good. I greedily sucked it all down, staying there and tasting every last drop.
“How did I do?” I asked, likely with some cum dripping down my chin.
“You were amazing, such a good little cum slut. I had a feeling you’d be good at this!” Bill replied.
Cum slut? I loved it! Sitting there in my nightgown, panties and pantyhose I truly felt the part. I slowly crawled up next to him and cuddled with his warm sweaty body. He put his arm around me and pulled me close.
Little did I know my night wasn’t even close to ending, in fact it was just beginning. Part 3 to come tomorrow!!
Also I’m working on a part 4 – part of the rest of what happened that summer, but with someone else.
Source: reddit.com/r/gonewildstories/comments/8umb3d/mm_losing_my_virginity_story_of_my_first_summer