Getting Fucked Again

I had just been fucked for the first time and I couldn’t wait for more.

I had just moved back home after almost 3 years away and almost immediately started a secret relationship with Jo, the guy 2 houses down from where I lived.

I had done gay things with guys before, blowjobs and anal sex but this was the first time I had been the bottom. It went so much further than I had ever fantasized or imagined. It started with just wanting to be fucked to see if I liked it and it ended up with me dressing up in women’s clothes and going the full distance.

Jo came over a couple days after our first night together and we had a good long talk about how we wanted to proceed with this relationship. We were both bisexual but he was more into guys than girls and I was more into girls than guys. My mom knew I was bisexual and I wasn’t worried about her finding out but my friends didn’t know.

I had only been back for about 2 months and I was already tired of living at home. I found myself a nice little studio apartment in the city and out of the suburbs which is what I always wanted. I felt a little more free and safe, in the sense that I could be who I wanted to be more openly.

Coupled with me not having as much spending money anymore and my new found desire to dress as a woman a little more, I had started to lose a bit of weight and my figure was getting slightly more womanly. When I moved into my new apartment, Jo got me a housewarming present. It was a tight black mini skirt dress. The first time I put it on it was a little tight, and I knew I had to drop a few pounds.

Shortly after I moved, I met a girl. Michelle. She was a model and cosmetology student. She was gorgeous but some of her personality traits were not really my type but I thought she could teach me to do my makeup a little better. I would let her practice on me and ask her questions and watch what she was doing.

The sex with Michelle had its ups and downs. She was a little inexperienced but she was horny and she moaned and screamed so much that I had to cover her mouth so the neighbors didn’t hear her. That and learning as much about being a beautiful woman kept me coming back for more with her. So much that I started to distance myself from Jo. Not because I wanted to but because I was just too busy.

One night Michelle found some of my women’s clothes including the little black dress Jo had gotten me. Of course her first instinct was to assume they were another woman’s and I was cheating on her. I wasn’t quite comfortable with the truth yet so l told her they were my ex’s and she hadn’t come to get them yet. She believed me.

That night she put a bunch of makeup on my face. When she was done she said she was very proud of how she did. She did a really good job.

“You could pass as a woman I did so well.” She said laughing “we should dress you up as a girl and see how hot you are.” She added

“Really?! I don’t know about that.” I said pretending not to be interested but my heart was pumping like crazy with excitement.

“Put that dress on that your ex left. I bet you could fit in that.” She said jokingly.

I knew she wasn’t really interested in seeing me dressed as a woman but I secretly wanted to do it. So I made a big joke of it and put the dress on.

“Why the hell not, it’ll be funny.” I said justifying it

I put the dress on and instantly noticed it fit better than it did a month ago when Jo gave it to me. Michelle laughed and said that I was totally passable if I had girly hair. I knew I had 3 different wigs in my closet but thankfully she didn’t find them.

“I gotta get a picture of this.” She said laughing hysterically

“Send it to me.” I said after she showed it to me

I told her that I wanted to send it to my mom as an April fools day joke but what the truth was, I looked fucking amazing, and the dress fit so I wanted to send the pic to Jo.

The next day I sent the pic to Jo with the caption “miss you”. It had been well over a month since we saw each other and I hadn’t dressed up for him since I moved into my new place which was now over 3 months. I was worried that Jo wasn’t interested and mad at me but he replied “miss you too, can I see you?”

Michelle was preoccupied with her final tests and a death in her family, so she had become very distant for a couple weeks. We didn’t break up just giving her some space to deal with things. It may seem incredibly insensitive given the circumstances but I used the opportunity to call Jo.

Jo came over and I was already dressed up for him when he got there. I was just wearing a blue silk nightgown that just barely made it passed my waist and a black thong. I had a black wig with shoulder length hair. The nightgown was his favorite but it was also what I wore to bed almost every night. I stole it from my mom and I had been wearing it behind her back since I was 11.

As he came in the door he was noticeably happy to see me dressed up for him. I wrapped my arms around his neck and gave him a big kiss.

“Hey Steph!” He said as he came in, short for Stephanie which is what I called myself when dressed as a woman.

“Hey baby!” I replied

I led him to the couch and sat him down, got between his legs and immediately unzipped his jeans and pulled out his cock. I put his meat in my mouth and started sucking him off. I missed his cock so much and I was really into this one! It was only a minute or so before he shot a hot load in my mouth. There was a lot of cum and it was dripping out and down my chin. His cum tasted great and I missed the taste so much!

“Wow! Thanks!” Jo said surprised

“It’s been a while and I gotta take care of my man.” I said in return. “ I’m gonna go get ready real quick.” I added

I made the decision that I wanted to try going out in public for the first time as Stephanie. I was nervous as hell but I wanted to try. We had made plans to go to a concert, seeing a local band. I knew that it’d be dark inside the venue so no one would notice and if they did, it’d be loud and I wouldn’t hear what they said anyways. Afterwards we went to a gay club, a very popular gay club that was just a couple blocks from my new apartment. I had been to this bar a few time and there’s an assortment of people there all the time including straight. I certainly knew no one would care there.

I started with my makeup. I had learned a few tricks from Michelle and she had left some stuff at my place that I used. She wouldn’t notice. When I was done and satisfied, I put on my fake tits chest piece. I had a nice set of B cup tits. I put on one of my garter belts and some fishnet stockings. I then put on the little black dress. I was so happy that it covered the edges of the chest piece. It was noticeable if you got really close and were looking for it but I didn’t care. Slipped on a pair of high heels and my wig again and went to greet Jo. He was stunned at how I looked and I was as well. I wanted to fuck me.

I gave him a quick kiss and then it turned into us making out. I had to put a stop to it or we would never leave the house.

We were only at the concert venue for about 45 minutes. We watched one band and left. Then we went to the gay dance club and danced for about an hour. While we were there, I noticed people looking at me. Some good and some bad, but I noticed some noticeably straight guys even checking me out. I was so horny and turned on!

“We need to leave!” I whispered in Jo’s ear

We made our way back to my apartment and couldn’t keep our hands off each other. I lived on the 6th floor and we he groped me all the way up the elevator. When we got to my door I fumbled for my keys in this tiny little purse that I had and Jo, standing behind me pressed himself against me and pushed me against the door. I felt his rock hard cock against my ass and his hands reached around and grabbed my fake tits. I was pinned against the door and couldn’t move. He seemed a little more aggressive than normal and maybe some would be scared but it turned me on so much.

I finally pushed him back enough to get the key in the door and open it. We both pushed thru and closed it as quick as possible. My door was in my kitchen and as I threw my keys on the island, Jo once again pressed himself against me. My hands braced myself against the counter and Jo ran his hands up my thighs and pushed up my dress. He yanked my thong down and my cock flew out. I was already dripping pre cum! Jo unzipped his pants and pulled them down. His cock hit my ass cheeks and his hands returned to my tits. He started to bite me on the neck and shoulder as his cock slid up and down between my ass cheeks.

“Goddamn I want you so badly!” Jo said as he spun me around and kissed me.

Our cocks slapped against each other. I grabbed his hand and started leading him to the bed.

“I’ve been dreaming of you cock inside me all night!” I said

When we got to the bed, I removed my dress. He got completely naked as well and sat on the edge. My cock was sticking out thru my garter belt and pointed right at his face. I had so much pre cum that it was stringing out and dripping down. Jo swiped it up with his finger and stuck it in my mouth.

I reached over and grabbed my lube and covered his dick and my hole. Pushed him onto his back and straddled him. I grabbed the base of his shaft and pressed it against my eager hole. I was so turned on and I had been using my dildos regularly now that I didn’t even bother to ease his 6” cock inside. I just sat down on his cock and it pushed inside my hole.

“Oh god that’s deep!” I said as I pushed him balls deep inside my ass.

I began to grind on him. His cock sliding in and out of my ass was sublime! It’s so much better than riding a dildo! Feeling a warm cock inside you that you have no control over how hard it fucks you is intoxicating.

“Make me cum baby!” I cried out feeling like I was about to explode.

Jo grabbed my hips and began to match my grinding fucking me harder and harder. My hands pressed against his stomach and me losing control once again over how sexy his abs were. He had been noticeably working on them since I told him how hot I thought they were.

I couldn’t take it anymore and I shot all my cum on his stomach.

“Don’t stop! Don’t stop!” I cried out

I hadn’t even finished cumming when Jo let out a grunt and pushed his hips upward and drove his cock as deep as he could. I could feel his dick pulsing and cum squirting inside my ass. I leaned down and began kissing him as we were both finishing at the same time. It was unbelievably intense!

As I sat up, Jo’s cock slid out of my ass and I felt cum dripping down my leg. I reached my hand down to wipe it up and couldn’t believe how much cum he had made, especially since he shot an unbelievable amount down my throat just a couple hours earlier.

I licked my fingers clean of his cum and tried to work up the courage to go suck his cock but I didn’t have it in me. It was just in my ass but the fact that I thought about it tells me that’s definitely in the future. Instead I licked my cum up off his stomach.

We were both so exhausted that we skipped the shower despite being covered in cum and sweat. We shut the lights off and just laid there until we fell asleep.

When we woke up, we both jumped in the shower. I still had my makeup, or what was left of it on. We kissed a little bit and both our cocks were hard again. I began to wash my face and while rinsing it off I felt something on my back. As I turned around and rubbed the soap and water from my eye I saw Jo was pissing on me. His cock rock hard and his stream not very strong, even stopping at times.

“What are you doing?!” I asked

“Just trying something, sorry I won’t do it again.” He responded ashamed a bit

“I don’t mind, it’s just kind of the thing you should tell me before you try.” I explained “are you into peeing and stuff?” I asked

“Yeah.. I know it’s kind of weird. I like it though.” He confessed

“It’s fine, I had your cum in my mouth last night. I don’t think piss is that much different.” I told him

“Can I try something?” He asked

“Why not.” I replied

“Do you have to pee?” He asked

“I did when we got in but now my dick is hard, I don’t know.” I answered

Jo pushed me back a step and grabbed his hard cock. He stood there for a few seconds and nothing happened. I felt like I had to piss as well but seeing him standing there with his hard cock in hand and the water glistening off his abs made my cock throbbing hard and I couldn’t pee.

Suddenly Jo started peeing. It hit my stomach at first and then he started aiming directly at my cock. He covered my dick in his piss and when he was done he quickly got on his knees and began sucking me. I was blown away at how quick this shower turned. I was also enjoying a spontaneous blowjob.

“If you feel like you can piss, just go in my mouth.” He said taking a breath before putting my cock back in his mouth.

I was so taken back. Suddenly he wanted me to piss in his mouth. Last time he reluctantly let me cum in his mouth.

His blowjob skills weren’t getting any better and it was about 3 or 4 minutes in I started feeling like I could pee.

“I’m gonna pee.” I said tapping him on the head

“Mmmhmm” he mumbled without stopping

I closed my eyes and just thought about peeing. Suddenly I started pissing. Jo started gagging a bit but he continued to suck my dick. Piss was drooling down his chin now as I was relaxed more and letting loose. When I finished he became very into sucking my dick. He was doing it the right way all of the sudden. Now I was ridiculously into this and within 30 seconds I came in his mouth.

Jo still spit out my cum for some reason but I wasn’t about to complain.

“Where the hell did that come from?!” I asked pulling Jo up to his feel and wrapping my arms around his waist.

“Been into pissing on myself for a while now and I wanted to try it with someone else. Again, I know it’s weird.” He explained

“I was thrown off at first but I was totally into that when it was done.” I told him

We finished cleaning ourselves and had breakfast…

To be continued….

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