It all started with an innocent blowjob

Everything started when I was in junior high. It was the beginning of the school year. At that time there was a flu epidemic so we were told to stay at home. I and my buddy Jack were spending the “vacation” at my apartment or my parent’s apartment to be more precise. My parents were at work and we played games on the PC all day. Of course, being young teenagers we only thought of 2 things, computer games, and sex. Our daily routine was, to play games, stalk some girl from our school, watch porn, and play games again. Being horny all the time, I masturbated 2-3 times a day, Jack did the same, but I was getting bored of watching porn and masturbating every day I wanted some new experience. Of course, I was too shy to ask a girl out and even if I did, I don’t think anything would have happened at that time.

Jack and I use to watch porn together, but nothing more, we never masturbated together or something like that, usually I waited for him to leave so I can relieve myself and I supposed he did the same. But during this flu “vacation’ something different happened. One day we were watching some porn as usual, but Jack was getting horny. He asked me if he can go a beat 1 quick in the bathroom. At that point, I didn’t care at all and didn’t mind so I let him. In the next couple of days that kept happening. Dude just wanted to masturbate at a new place, I get it I was bored with it all as well. But after maybe a week of that he asked me something strange. This is maybe a good point to mention that my mother was a really beautiful woman. I am mentioning it because she used to wear these tight skirts and high heels every day to work. I have caught a few of my buddies checking her out, it bothered me, but I never said anything because it was nothing more than a boy seeing a beautiful woman. Because my mother only wore high heels, there were a lot of high heels shoes in the hallway. And since they were all at least 4 inches and above high, they were similar to the shoes girl wore in porn movies. Getting back to the point, Jack asked me:

“V, can I use your bathroom again, I’m so hard at the moment.”, he asked.

“Yea dude no problem go ahead.”, I replied.

“But dude can I make a strange request; can I use a pair of your mother’s heels? I just want to watch them as I masturbate, it will help me finish.”

“Wtf dude, that’s strange.”

“Please dude, they look like the ones in the porn movies, it will help me so much.”

I don’t know why I agreed to it, but I let him take a black pair of boots my mom had laying around. He came back a few minutes later and we didn’t speak of it again.

The next day we were still on “vacation” and after a few hours of gaming, he asked me straight away if he can use a pair again to masturbate. I agreed and gave him a red pair of very classy shoes, they were very high and thin heels and looked like something a porn actress or a whore could wear. This time I was interested in what the hell does he with them, I didn’t want to ask, but I was curious. The bathroom didn’t have a key, so there was a little hole in its place and I could see true it. I could see him, he had placed the shoes on the side and he was vigorously masturbating over the toilet bowl. At first, I could only see his back, but after a minute he turned around and I could see his hand, holding his dick and stroking it fast. He was average size, the same as mine, cut, and he didn’t have any hair down there, he was smooth. He started to moan, and I could see his body twitching as white cream was coming out of his cock. I was fascinated, nothing new to see I had seen 100 guys come in movies but this was different, I started to lick my lips involuntarily while he was ejaculating. After he was done I realized what I was doing so I quickly returned to the other room before the realized I had watched him the whole time. This happened on the last day of the week and the end of our flu vacation.

After that Jack never asked to masturbate again at my apartment, we were busy with school and so on and we didn’t have as much time to hang out as before. I mean we still did, we still played games and hang out, but that was pretty much it for the next few years. Back at school I never checked out guys or anything, I still liked girls and wanted to have sex with them, but I wasn’t the best-looking guy and I was a bit shy. So the next year got by and I had a normal school experience, except for the fact that I always remember watching Jack masturbate in the bathroom with my mother’s shoes.

True the next few years, I started to watch all kinds of porn, not only “regular”. I started to go to forums read people’s stories and checked a LifeCam or 2, I wanted to see it all. But after a while, I would again get bored and move to something new. Every day when I get home around 3, my parent would still be at work and I was home alone. One day while I was getting out of the shower I noticed a pair of my mother’s panties on the dryer, I don’t know why but I wanted to try them on. I was a big boy so they were light-tight, but still, I managed to put them on, I could feel my balls getting squashed, but I licked how they feel against my skin. I quickly took them off and that was it for the day. I tough of that moment all night, so the next day I decided to try them out again. This time I checked myself in front of the mirror. You could see my balls trying to escape to the sides. While watching myself in them my dick started to get hard and trying to jut out of them. That night I started to search and watch, guys dressed in woman’s cloth. I didn’t get much sleep that night. The next day, I decided to check what else is there in my mother’s underwear drawer. She had a lot of panties, but even more thongs, also pantyhose, bras, and so on. I picked up a pair of dark blue thongs, which seem larger than the rest, and put them on. The strap on the back went in straight into my ass, I could feel it grinding on it, my balls were getting smashed by the band, and my dick could barely fit in them, but I kept pulling them up, I enjoyed the feeling of it. While watching myself in the mirror, turning to the side to see how my butt looks in them, I didn’t like the way I normally look, but this was hot. I picked up a bra I could put on, stuff it with a bit of toilet paper, and put on a tiny tank top, to mimic a girl with boobs, I was still only in the panties, but I tried to find some shoes that fit my big feed. I tried to put on some sandals with high heels of course and even though they were too small for me, I still manage to stand in front of the mirror and took some pictures. My dick was getting hard and trying to come out of the panties, so I pulled them down, just enough to get it out, while the panties were still smashing my balls and ass, and started to masturbate. It didn’t take me more than 2 minutes to cum right there in the hallways in front of the mirror. I took the shoes off and grab some paper towels to clean my cum off the floor, right at that moment I heard the key and someone opening the front door. I rushed straight away to the other room, my father came home early today and almost caught me like that. I quickly took off the tank top and bra, hid them under my pillow, and put on some shorts and a t-shirt, like nothing has happened, with the thong still on me. I spend the night with the thong, and since I didn’t get a chance to go and change, I could feel the band rubbing against my ass all night. After that day, I started to try new stuff, I was afraid to get caught so I was very careful when and where I also didn’t want to stretch out any cloth so I was very picky with them. I also started to put stuff in my butt, my finger, a toothbrush, and so on.

I was almost 19 years old now, still a virgin except for the stuff I did alone of course. I and my buddies were still chasing girls, and I had my little secret on the side. A couple of months back, my mom was cleaning and she gave me to throw away a lot of her old clothes, which I didn’t do, and now I had a ton of cloth to dress up and not care if I stretch them out or not, I even ripped a couple while trying to put them on. I was having fun, dressing up from time to time, I even bought a small vibrator from a local sex shop, to play with. I normally didn’t even enjoy the feeling of it getting inside my ass that much, but when dressed up or horny for a few days, it was wonderful. I would stick it with some duct tape on a wall or the side of the bed and I would sit on it and fuck myself like that. I never thought I would do anything more than that, I was just experimenting I was saying to myself.

It was the beginning of the summer. I didn’t spend much time at home, always out in one place or another, but It was a very hot day. Everyone was at home to beat the heat and I was bored. No one wanted to go out, so I decided to check what my old buddy Jack is doing. His parent had another child a few mount back so I rarely so him now since he was helping out with the baby. I called him and he was free so we decided to hand out for a bit. We were chilling at the part, walking around catching up, but it was scorching hot outside, so I invited him over to beat the heat and chill at my place, like old times. We were just chilling and reminiscing about old times. We were checking girls from each other schools and so on when he mentioned that there is a rumor, that one of his classmates was filmed during sex. We started to search around till we found the said video. She was down on her knees, sucking some old dude’s dick, it was really bad quality, but you could tell it was her. I noticed Jack’s pants growing, and he started to pull his pants aside, moving in the chair, it was clear he was getting hard.

“Man stop it; I’m getting too hard it’s starting to hurt.” – he said.

“What the matter? You like this girl or something?” – I asked.

“No dude, I just haven’t masturbated in a while, with the baby and all, don’t have much time alone lately., and I’m afraid I could come in my pants from just watching this.” – he replied.

We stopped the porn but kept watching and talking about it, and my eyes keep locking down his pants, his erection wasn’t going down.

“Man I would do anything for a blowjob at this moment, why are all the girls so lame?”- he said.

“I don’t know man; they should be more like her.”

“Dude I’m going crazy, my balls hurt, do you mind if a jack one off here? I want to finish the video and jack on it. Please I know it’s weird, but I’m going to burst soon.”

I paused for a moment thinking of what he wanted to do, me in the room and him jacking off right in front of me. I mean I have watched gay porn and dressed in woman’s cloth, but a cock right next to me, I don’t know how I’m going to react, would I ignore it or I would stare, I have heard some of my other buddies talk, that they have jack off together and so on, but I have never done that. I \wanted to see it again, and maybe even touch it but still, it was weird to me.

“I don’t know dude, it’s kind of weird with me being here, and I don’t feel like leaving so you can jack off here.”- I replied.

“O, it’s okay dude, I have done it before with Nick (that’s one of his cousins), we just jack off together while watching porn, and we didn’t even look at each other, it's not that weird, you can do it with me, come one.” – he said.

I wasn’t sure about it, but I tentatively agreed. We put the video back on and he didn’t waste a second he pulled his dick out and started to masturbate. I leaned back on my chair and took out mine as well, but I could not get hard at that moment, and I kept turning my head around to watch him masturbate, my eyes kept fixating on his cock. He was better looking than me and still perfectly shaved down there, from the heat that day I could see the sweat on his balls, dripping down as he was moving his hand up and down his junk, so much so that I started to sweat as well, not sure if it was the heat or something else. It didn’t take long for him to cum in a napkin nearby, while I was still soft, so I put my back in my pants and that was it for the day.

After that event, he came back the next few days, and every day he asked me to jack off at home and I let him. This time I managed to get hard and join him so it’s not that weird, but for a whole week my eyes kept turning to his cock. I even licked my lips a couple of times, involuntarily, but still, I believed he noticed that. It was Monday when he called me that he is coming back from the gym and he was passing by my building and if I want to grab a coffee or something and hang out. I agreed. So we grab a coffee and were sitting in my room just lessoning to music and talking, after an hour or so, he straight away asked me if I want to masturbate together, and I agreed. We put on some movie and started to slowly stoke our cock, but again my eyes kept finding his cock, until:

“Dude do you want to stroke each other cocks?” – he asked me.

“What?” – I replied.

“Stroke each other, it will be new, different, maybe a bit weird, but I bet it will feel great. Come one and we will do it at the same time so it will be weird for the both of us.”

“Ok.” – I said with a trembling voice.

We lay on the bed, with the porn still going on the PC, next to each other, and we grab each other cock. It was strange having another man’s dick in my hand at first, but as I started to move my hand up and down it felt nice. In the meantime, I could feel his hand on my cock, he was squeezing much harder than I normally do I could feel I want to finish very fast. And there it is after just a few minutes I started to cum all over his hand and myself, he grabbed a napkin to clean his hand and made a joke about how fast I came. I kept stroking his cock, since the agreement was for him to jack me off and vice versa. He told me that my hand is too dry and that it hurts a bit if maybe I have lube or something, I did, but it was hidden with my vibrator so I told him no, so then he asked me if maybe a could spit on my hand and rub him off like that. I agreed, but for some reason instead of pulling my hand spitting on it, and rubbing him again, I leaned down to his cock, spit on top of his head, and started to play with it using my finger, to rub the spit all over. I didn’t even realize my head was this close to his dick before I leaned again and spit some more on top of his head. My lips were only a few inched away from it when I heard:

“You can lick it if you want, I don’t mind.” – he said.

“What?” – I asked, not even realizing where I am at this moment.

“I noticed how you stare at my cock sometimes, and I mean you almost did kiss it just now. So if you want to I will be ok with that.”

I was confused as to what is going on at the moment, did he just offer me to suck his cock.

“Just a quick lick, or suck to try what it tastes like, I will return the favor tomorrow I promise. I want to see what it feels like, for someone to lick your cock, maybe feel lips wrapped around it. Just for a second.” – he said.

With his cock still in my hand I leaned forward and just put my lips on top of his head for a second, I pulled right away, and try to lick the top of it very gently. To be fair I have sucked my dildo before I just didn’t want to see like this is something I want to do. With every lick I started to get bolder, I licked the head, and went down the stem, until I just went for it, I opened my mouth and took it inside, just slowly up and down inch by inch, until I had almost his entire dick in my mouth, I started to suck him faster going up and down, moving my hand up and down as well, giving him a full blowjob to be fair. It didn’t take long for a hit to start shaking, I moved my head away just in time as he came all over my hand and his pants. I picked up a napkin to clean my hand as he said:

“Wow dude that was the best thing ever, I have never cum so hard before.” – breathing heavily. “You ok? It wasn’t too weird I hope?”

“I’m fine I said, but remember tomorrow is your turn.”

“Yea you got it.”

He was still breathing heavily, head down on the bed with eyes closed, which gave me the perfect opportunity to lick the side of my hand without him noticing, I needed to try the taste of his sperm. I had tried mine before and I liked it, but I have always wanted to try someone else’s sperm, his was a lot saltier than mine, but maybe I need to get a mouthful just to be sure. That night I kept repeating the event of the day, I could not get the taste of his cock out of my mind, how it felt in my mouth.

The next day we meet up in the afternoon, and we talked for a bit, but I was eager to not waste time, not so much that I wanted to get my dick wet, but more so that I wanted to suck his cock again, of course, he didn’t know that at the time. Once again we put on some porn on the PC and we lied down on the bed next to each other, we started stoking each other cocks again. After we were both hard, I was just slowly playing with his cock, I didn’t want him to come before I got my taste again, on the other hand, he was speeding up and stroking my cock as hard as he could, I’m pretty sure he just wanted to make me cum so he doesn’t have to suck my dick:

“Dude slow down, or I’m going to cum. And you still owe me a blowjob.” – I said.

“Sorry I just got carried away.” – he replied.

“That’s ok, now you ready? Go down there and let’s see what you got.”

He got up on his knees next to me while I was still laying on my back, he was slowly stocking my cock and just looking at it:

“Come on man, do a little spit, rub it in, then a little closer and you will get it.” – I was eager.

He spits on his hand and rubs it in, after a few moments he did it again on top of my head, and started to play with my cock head and rub it in. He got closer to it, but he looked afraid, he got his lips on my head for half a second, before pulling back, I didn’t say anything, then he put his tongue out slightly and tried to touch my cock with it. Then he pulled back and said:

“Sorry V I can’t, it’s not me, I don’t like it. Sorry I made you do it.”- he said.

“Come to one Jack, we had a deal.” – I replied.

“I’m sorry man I just can’t, I don’t like it.”

“How can you not like it, if you haven’t even tried it?” – I replied, hoping I can play this to my advantage.

“I will make you a new offer, you suck me now as we agreed, and after if you want I will blow you again, no strings attached this time. I want to see if you like it. Deal?” – I offered him.

He hesitated for a moment, but knowing how horny he is all the time, I was sure he will agree. Then he nodded and again went down to try and suck my cock. His head was just over my dick, he opened how to mouth a little and started to kiss the top of my head, very slowly going down on me. He would pull back up and try again, after a few tries I offered to help, I grabbed his head while his mouth was already on my cock, and instead of pushing down I lifted myself a bit and started to fuck him in the mouth, holding his head so he can’t run away. After a minute of trust, I relax down on the bed, and I could he kept moving up and down, sucking my cock out of his own free will now. I’m not sure how much he enjoyed it, but he was now blowing me, playing with my cock with his hand, licking the stem while watching me straight into my eyes. I had a huge smile on my face, watching him down there while he sucked my cock. I had also shaved btw, my cock balls, and my ass, mainly because it felt nicer when I was wearing a thong. When I was close to ejaculating I warn him and he pulled his head back and finish me off with his hand, then again clean up using a napkin.

“Did you like it?” – he asked me.

“Yea it was great, you are good at this. But the important question is, did you like it?” – I replied.

“It wasn’t as bad as I expected, I felt sweet and nice, to be honest, but I prefer getting my dick sucked. But I won’t force you if you don’t want to, alter all you already sucked me off ones.” – he replied.

“And did you like, how I sucked your cock?” – I asked.

“O man, best feeling ever, I loved it.” – he said.

“Well seems to be, you enjoyed sucking my cock as well since you are still hard. It will be wasted not to take advantage of that erection. And I did promise you if you blew me I will blow you back so…” – I replied.

I told him to sit on the edge of the bed, and I kneeled on the ground right in front of him. I was on my knees, but I had spread my legs a bit so my dick would touch the floor, I wanted to feel the cold floor for some reason. My dick was still leaking a bit of cum, and I could feel it dripping down on the laminate. It didn’t take me a long time to get down to business, I had grabbed his cock with one hand, at the base, playing with his balls with the other, while sucking at his cock. I could hear him moan from the feeling I was giving him.  I was very focused on sucking his cock, but at one point I wanted to lick his balls as well, I grabbed his dick and lifted it while sticking my tongue out and licking his balls. Our eyes caught up, he was watching me tight in the eyes, while I had my tongue out and I was licking his ball sack. Without breaking eye contact, I moved back to his sock, sucking him dry, and playing with it. You could hear the noises of me sucking his cock, going up and down, saliva dripping down his balls. I was trying to take it as much as I can’t before I start to gag. Then going up to take a breath and sucking it again as much as I can. I will never forget the surprise and joy on his face at that moment. I’m convinced he realized at that moment that this will not be the last time I suck his cock.

He told me he is going to cum any moment, with the expectation I will move, but not this time. I kept sucking his cock, until I felt the warm creamy substance in the back of my mouth, at which point, I wrapped my lips tight around his head and started to gather all the seamen. I could feel the pleasure as he ejaculation in my mouth. After he was done he locked down on me, and I was just getting my mouth off his cock, then I showed it to him, mouth full of cum, dripping at the side of my mouth. I swallowed the whole load, before sticking my tongue out to show him, and laughing at the same time:

“Wow dude, what was that?”- he asked.

“I just wanted to see what it feels and tastes like, it’s not bad at all.” – I said with a smile.

“Lol man, are you into this stuff, have you done this before?” – he asked me.

“Well I did yesterday, but besides that no, I just felt like it. Did you enjoy it?”

“Best day of my life.”

“Good, if you are lucky it might happen again.” – I replied while getting up and licking the rest of the sperm out of my fingers.

He had to go, so we washed up quickly before he left. I still had the taste of his cum in my mouth.

The next day I wasn’t expecting him to call me, since he was supposed to be busy. But here we were at 11, and he called and asked me if he can come by, I agreed of course. We talked for a few minutes before he started to ask me questions, about how long have I wanted to suck cock, or if it is something new, do I like guys, whether have I been with someone else, do I watch gay porn, and so on. But I told him that this was something new, and it all started because he wanted us to jerk off together and that this was something I wanted to do at the moment. He didn’t buy it, but dropped it for the moment and asked me if it was something I feel like doing again, now. I smiled back at him and said:

“Sure, but I want something else first.”

“Like what?” – he asked.

“I want for us to make out first, just to see what it was like.”

He tentatively agreed, it was a little awkward since none of us kissed a guy before but still. I leaned toward him and gently kissed his bottom lip, then I went for a full kiss, before feeling him kissing me back, after a few gentle kisses we started to use our tongues and there you go we were making out, just as a normal couple do. I don’t know why, but after a few moments, he grabbed my ass and pulled me toward him. I on the other hand grabbed his ass with one hand, while cupping his balls with the other. We were both standing up, making out before I stuck my hand down his pants, grabbed his dick, and started to play with it. I could feel him getting hard in my hand. Without saying anything I squatted down, and started to unzip and pull down his jeans, after which I took his dick out of his boxer and just started sucking it. Licking it up and down, gently biting his head, and then sucking it all up. At one moment he grabbed the back of my head and started to pump me in the mouth. You could hear the gag noises and how he was slapping my mouth with his cock. He let me go to finish at my paste, at which point my hand was on his ass, grabbing and squeezing him. Moving my fingers, a little closer to his anus, I was sucking his dick hand free. After a few more moments of deep throat and he was Cumming in my mouth once again. This time I let it spit all over my face, spitting it out back on his cock, sucking it off again, and letting it drip down the floor, except for the part I swallowed. I stood up and winked at him, before going to the sperm off my face. I guess he just came by for a blow since he said he has to leave right after, good thing I didn’t mind.

It was now Thursday, we were texting all morning and he said he was busy helping his mother to watch his brother and so on. Remember we were still friends for more than 10 years, we were chatting and played games all the time, so we were in touch all the time, and we did live very close to each other, so it was not strange if people saw us together almost every day. I didn’t have any plans for the day, so I was just on the computer watching videos and chatting with people. It was almost 17:00 when Jack texted me he was going to the store and if he was on the way back he can come by to get his hat, he had forgotten it the previous day, so I said sure. My apartment was on the 3rd floor, and it was the only one occupied out of the 3 there. It was 17:10 when he rang the bell, and I went to open the door. It’s good to mention that my father comes from work around 17:00 to 17:30, so I didn’t plan for anything since I did want to get a cough under any circumstances sucking another man’s dick. On the other hand, I could always hear someone coming up the stairs, and there was no one else that can come out since the other apartments were empty. I opened the door and gave him his hat, he said thank and that he will text me later, and maybe if he is free we can hang out tomorrow, I said sure, but right as about he was ready to go down the stairs, I pulled him back, put his back against the wall, right there on the stairway and stuck my tongue down his mouth, I told his I need to give him something else, before whispering in his ear to be quiet. As I kneeled once again and pulled his shorts, to reveal his smelly and sweaty cock. It didn’t take more than a few seconds for him to get hard. I was jacking him off while swallowing his cock, the idea was for him to cum as fast as possible since I didn’t know if we will even be able to finish as my father could come home any moment, and he was also in a hurry to get home. Good thing it didn’t take too long for him to start Cumming in my mouth again, swallowed some, careful not to drip on the floor, before leaving the rest in my mouth. I then stood up, pulling his pants back up in the meantime, and went for a kiss, forcing him to drink his cum out of my mouth. He wasn’t expecting that at all, but he still swallowed it, and to be fair it wasn’t that much, to begin with. I told him that this was what I wanted to give him and said bye, before going back inside. 2 minutes later my father came home, and I was still washing the sperm off my mouth. Good timing, I thought.

The next day – Friday, I was up early, Jack texted me that he will be free around noon and if I want to hang out. I agreed. He wanted to walk around town and hang out not only to come to my place, and maybe later if was in the mood he was up for something else. But I told them it’s better to come by first, while I was alone and then we can hang out. We were at my place again, and he was explaining to me how he enjoyed Thursday’s quick encounter, especially the end. I laugh since I knew he was going to like that. As I was just finishing up an email on my PC, I felt his hand on my dick. He told me he felt bad that only he got his dick wet, and even though it wasn’t his favorite to suck cock, he wanted to suck mine, and he wanted to taste what my sperm tasted like as well. He was sitting next to mean leaned down to suck my dick, and just as he was getting ready to go down to the floor and start to suck it, I hear keys and the front door opening. My mother came home, greeted us, and told me she forgot something. I went to the kitchen to talk to her, but I forget that my pants were unzipped. She told me to pull my pants back up, and said it was rude to stay like that while I have guessed if only she knew. I told her I was just getting dressed and we were going out, she told me to have fun and left back for work. The moment I went back to my room, I pulled my pants back down and slapped Jack’s face with my cock, he didn’t need a second invitation to put it in his mouth. We started to get undressed and ended up on the bed, in 69 with me on the bottom. He was sucking my cock, while jamming his down my throat. I was grabbing his ass while sucking, and my finger slowly started to move to his asshole. The moment I lightly touch it and try to push my finger inside, he jumped up and told me he is not into that, all the rest was fine but not that, so I told him to relax, before forcing him onto the bottom. We finished up pretty much at the same time, with him drinking most of my cum, before I turned around to him, and kissed him with his cum still in my mouth again. We started to make out with sperm-filled mouths, swallowing every last drop. After he said he liked the taste of my semen more, but I disagreed. We got dressed and went out.

                                                                                                                       

Saturday and Sunday we were both busy, and we didn’t have a free field for anything so the days were pretty normal. On Monday I was hoping something will happen. I normally masturbate at least once a day, but since last week, I decided I want something different. He didn’t have the time to meet up during the day, but we still saw each other in the evening. I was very horny now, and I could feel my ass itching, at first I thought this will be it, just a blowjob now and then to take the edge off, but now I was ready for more, but I didn’t know how to bring it up. I knew he didn’t want anything near his ass, but what about if I offered mine. We were sitting on a bench talking when he once again started to ask me questions. I decided I want to admit some of the parts. So I asked him:

“Do you remember a few years back, with the flu “vacation”, how you jacked off in my bathroom with my mom’s shoes?”

“Yes I remember” – he replied. “Since then” – he asked.

“No not really, but after a while, after that, I was also bored of masturbation the same as you, and I started to search for new things. That is how I found gay porn, guys sucking each other cock, guys dressed as girls, girls with cock, and so on.  Then I started to read stories and forums about people’s experiences and I got curious. So I started to watch and read more and more. Then a few times after that every time I came I tried to taste my sperm, but I could not when I finally managed I didn’t like it at all, but after a few months I started to crave it again and I started to taste good. I even played with my anus, rubbing it with a finger or sticking a toothbrush inside.” – I explained.

“Really, do you like that? For me I don’t think will like it, the blowjob is one thing but this, not so much, and I still like chicks who don’t get me wrong, I still want to fucked so many of my girlfriends.” – he replied.

“Relax dude, me too. This is just something different I wanted to try and see if I like.”

“Do you think you would like want, to take a dick up the butt at some point?” – he asked.

“Yea, maybe I don’t know yet.” – I replied, hiding the fact that I have already fucked myself with a dildo several times, and I did enjoy it, not to mention all the girl clothes I wore.

We talked for a few more hours before going home. The next day I had to get up early since I was going out of town, so one more day when it will be dry for me.

The next night we texted and I invited Jack to come over the next day, I knew he was super horny and wanted to come over as well. At night in bed, I was thinking if I should do something more with him, maybe a little dress-up would help with the process. The next day he came over as agreed, fully expecting what will happen. We both knew it, and since we were both so horny, we got straight down to business. We were laying on the sides facing each other sucking each other cock. He came super-fast, I guess I’m better at blowjobs, but after he came he kept going, he kept sucking me off, which I didn’t expect to be honest I thought he will probably just finish me off with his hand. I was just enjoying his lips around my cock, and the taste of his sperm was still in my mouth when I felt him getting hard again. After he came I kept playing with his balls and cock, but didn’t expect him to get hard again so fast, well it’s not a good thing to waste an erection so I blow him one more time. Our experience so far was pretty good but I kept wanting more. And there were only 3 months before we went to college so I didn’t want to waste much time.

We could not meet on Thursday, which gave me more time to prepare for my Friday plans. I shaved my dick, ball, and ass, really good, picked up a little red thong, and black pantyhose, they were a little ripped but who cared, I didn’t have the bra to match the thong, it was more pink but still. I got a little white skirt, which didn’t fit, but I manage to put it on, and a small white tank top. I was looking at myself in the mirror, it wasn’t great, but if you looked from the shoulders I didn’t look bad, my face even shaved didn’t look anything like a girl, but that was the best I could do. None of my mother’s boots fit me, but I found a pair of high-heel-open shoes that will work, not that I needed them, but I wanted to get the full picture.

Friday came, and Jack came by around 11. We hang out for a bit before he asks me if want to do it again, but I told him I have a surprise today and for him to be patient. I was scared of us getting caught, it was one thing to be naked and if someone came home, we can put on a shirt and pants in a second we hear the door, and even if we had only pants on, not that weird, it was summer, but this, it took me 15 minutes to get dress and at least half of that to get undress, but the risk made it even more exciting. I figured the best time is between 13:00 and 15:00, it was not noon, and hopefully, no one will come home before 15:00. At precisely 13:00 I told him to relax and that I will be back in a few minutes, I had a surprise for him. He had no idea what to expect. I got dressed as fast as I could, so far so good. I told him to close his eyes, before walking into the room, you could even hear the heels while I walked into the room. I went to him and kissed him, while placing his hand on my waist, before telling him to open his eyes. He was stunned at the sight.

“What is that? What are you wearing?” – he asked while checking me up and down with his mouth open wide.

“Do you like it?”

“I loved it, it’s amazing, but what made you do this?” – he asked

“I will explain later for now, do you want to feel?” – asked him while touching my legs.

He just nodded and I went close to him. He was staring and touching my whole body, from my empty bra, down my ass, and slowing down my legs to my shoes. I even told him to kiss my toes which he did right away. He was sitting in a chair when I pushed him back and kneel in front of him. I took his t-shirt off and pulled his pants down, he was already hard. So I started to play with his cock, stroking it and sucking it softly.

“Do you like me like this? Dressed like a slut, eager for a cock.” – I asked.

“Yea, yea, yea.” – was the only thing he manage to say.

“Do you want to punish this bad girl; do you want to slap my ass?”

The moment I said it, he leans forward and started to slap my ass, hard. It felt nice and I tried to make the noise that a girl will make at that moment. I stood up, and step off the heels, they didn’t fit anyways, then I slide off the skirt which also didn’t fit well, exposing my ass. At that moment he realized that I was also wearing a thong, I stepped on the bed on all fours, ass facing him, before asking him to punish me some more. He came behind me and slapped my ass a few more times before I turned around and started to suck his cock again.

“So what do you think, you want to try it? – I asked.

“Try what he replied?” – he replied.

“My ass, do you want to fuck me in the ass?”

“Are you sure?” – he replied.

I stood up and went to my desk drawer, I took a bottle of lube and a condom from there. I gave him the condom and told him to put it on, before starting to pull down the pantyhose and panties. I went back to the bed, and he was next to it, struggling to put on the condom. I helped him, and then took the cock in my mouth again, I prefer it bare, but for the first time, I wanted all the lube I could get. I turned around and poured a bit of lube over my ass crack, and asked him to rub it in with his finger, slowly pushing it inside if he can. He started to rub it in on my hole gently all around the ring, before starting to push his index finger inside. It was a good amount of lube and I did practice with my vibrator the night before to get ready, so it went inside with no trouble, I then squirted some more lube on my ass and he again rubs it in and put 2 fingers inside this time. He was finger fucking my ass with both fingers for a few minutes, asking me if I’m all right and if it hurts. I told him it feels nice and to keep going. I was getting horny and hard from his fingers, so I raised, ass still toward him, pulled him close by his dick, put some lube on my hand, and rubbed it all over his cock, I put some more on my ass, and then positioned his dick behind me. I was on all fours and told him to go slow. His head was on my asshole, and he started to push slowly inside of me, even though my ass was ready and lubed up properly I still felt pain. But it wasn’t too bad, didn’t even realize he was already inside of me. He started to pull out but I told him to wait like that for a moment. It still felt a bit weird and there was pain, so I gently pulled the dick out of my ass and told him we will try another way. I told him to sit down, and then I mounted him face-to-face. I slid that cock inside of me slowly, and with his dick inside of me, I started to kiss him. Taking my mind off the pain for a moment helped, since only after a few minutes I started to go up and down on that cock. I was moving very slowly, the same way I used to do with the dildo, my hand was wrapped around him and I asked him if it feels good. He said that it was amazing, very tight, something he never felt before. This felt nice now, the cock inside of me, but I didn’t want to jump on it, I wanted him to fuck me, so I stood up, his cock falling out of my ass, and I stood again on all four on the bed, and told him to fuck me. He didn’t need a second invitation, he placed his dick again on my ass and started to push, slowly penetrating me. This is what I expected, this is what I craved. With every stroke I could feel him deeper inside of me, he was also picking up speed, holding me by the waist. I could feel my semi-hard cock dangling under me. I could feel the pre-cum dripping out of it, I was moaning so loud to the sound of his tights slapping my ass. I’m sure that at that moment if someone came home we would not notice, and at that moment I didn’t even care. I was stroking my cock almost ready to cum, when he pulled out and turned me over. He put my legs on his shoulders and started to fuck me like that. I was still moaning with every thrust, stroking my cock. After a few more strokes, he pulled out, took the condom off, and started to cum all over my body, some of it even reached my mouth. He collapsed next to me on the bed, while I was still stroking my cock, ready to cum any second now, covering myself with my cum as well.

I was laying on the bed next to him covered in cum, and didn’t have the strengths to was up, but I knew I had to. Before getting up I asked him:

“Did you like it?”

“I loved it, I want to fuck you again and again.”

“We can work with that I replied, before going to the bathroom.”

Later that day I explained to him how I dressed up, from where did I get the clothes, and so on. He was very excited about the opportunities that will come with this revelation.

This was my first time with Jack, and there was a lot that happened in the next few months, with a ton of surprises. If you enjoyed the story so far please keep reading it, even though it might not be so full of details. The second part of the adventure is going to be a bit different.