I was in a lull with dressing as a woman until I met him.
I hadn’t been with Jo in almost a month now because I had been spending time with my girlfriend Michelle. Even though I had more sex with men, Jo, and Jayson were both boyfriends of mine, I still considered myself very straight. It started years ago with me and Jayson where I was always the top but it progressed to Jo where I went as far as dressing as a woman, calling myself Stephanie and letting Jo fuck my ass.
Michelle and I were relatively new to each other, only dating a few months but we were having a lot of sex, a lot of good sex and I began to forget all about Jo.
I still found comfort in dressing in womens clothes around the house when no one else was here. I’d had a fake breast chest piece that I wore and I’d put on one of my wigs and just some comfortable girly pajamas and watch tv or play video games.
After a month or so away from Jo though, the sexual thoughts started creeping into my head. So much until one night I got all dressed up as Stephanie and went to the gay bar down the street from my apartment. I picked up a guy, brought him back to my place and sucked his cock. I wanted him to fuck my ass so bad but he was rather big and I still wasn’t the most comfortable with a stranger being as gentle and patient as I needed him to be. Nevertheless, I sucked his cock and swallowed every drop of his cum and it was amazing!
A few days had gone by and sucking that guys cock no longer was enough, I wanted more! I originally picked Jo for this fetish of mine because I knew his cock was somewhere in the 5”-6” range and not too thick. It was easier to take in my tight hole. I have a dildo collection so to speak, that has bigger size cocks but it’s different having a guy behind you pounding your ass then when you’re ramming it home by yourself in your room.
I gave Jo a call and asked if he wanted to get together. He was a little upset I hadn’t called in over a month but he agreed to meet. We decided that we were going to meet up on Friday night which gave me a couple days to get ready for him. I starved myself until our date to look as thin as I could, and I shaved every hair on my body for him.
Jo didn’t have a car so I went to pick him up and bring him back to my apartment. I went as me, leaving Stephanie at home because Jo still lived two houses down from my parents and in a neighborhood that everyone knew me.
I knocked on his front door and his sister opened the door. I was a bit taken back as she was my first crush and I always had a thing for her but never had her. Jo eventually entered the room and acknowledged me then turned and continued his conversation on the phone. When he finished, he mentioned we had to stay and wait a few minutes for his cousin Nicholas to come over. He was going to fix the furnace.
When Nicholas walked in, our eyes met immediately and I was speechless. As I said, although I have had more sex with men than women, I consider myself very straight. Jo and Jayson are certainly not ugly but I wouldn’t call them hot either. In fact I had never in my life considered a man attractive, the ones I had been with sexually, were just ways of getting off and pleasuring myself more than anything. That was until now. Nicholas was an absolute stud! Holy shit what a body he had! He was 6’3” and chiseled! His shirt was on so tight that I could see his abs definition. His biceps were stretching the sleeves on his t shirt. His blue jeans were even tighter and I could see a nice bulge in his pants.
We didn’t have long and barely spoke but we locked eyes for a while and had a weird connection. I took Jo over to my apartment and did the full dress up for him and we had some pretty great sex. It was completely enhanced by my brain not being able to stop fantasizing about Nicholas. I pretended I was sucking his cock instead of Jo’s. I pretended it was Nicholas behind my thrusting his cock deep in my ass. When I kissed him, I dreamed of Nicholas’ tongue dancing with mine. I was already in love with a man I hadn’t said more than 2 words to.
After Jo and I were done, we showered and cleaned up. I asked him casually about Nicholas and what his story was. He mentioned that he had just lost his job and his girlfriend dumped him all within a couple weeks so Jo’s mom was throwing him a bone by paying him to fix some stuff around the house.
I told Jo that I needed some stuff fixed as well and my landlord wasn’t in any hurry to fix it. It was a lie, but a believable one at that. Jo agreed to give me Nicholas’ number, and my heart raced. I had zero expectations of course, he was obviously a very straight manly man, but if I could just see him, then pleasure myself after he left, that’d be awesome.
I called Nicholas and asked him if he’d be able to stop by and look at some things and we’d decide what needed to be fixed first. I intentionally went in the back of my toilet and broke some stuff just so I had something to show him. I pulled of some wood around the bedroom door frame as well.
Nicholas called and said he’d be over in a couple hours and I was so excited. I took a bath, and again shaved every hair on my body. I used Michelle’s lavender body wash and lotion so I’d smell like a woman. I got everything I would need to fully pleasure myself afterwards ready to go.
Nicholas knocked on my door and my heart raced. As I opened the door he smiled and our eyes locked again as I signaled for him to come in. We were both quiet and shy. We didn’t say much. He looked great though. He had the same tight blue jeans on and as I watched him examine the toilet, I examined his ass and muscles.
As we moved throughout my apartment, me showing him what needed to be fixed we began to open up. He mentioned his job loss and his girlfriend leaving him. He mentioned that he was lonely and I lost it. I wanted him so bad! I wanted to push him against the wall, unzip his jeans and slobber his cock so bad! I held back a bit because I was so scared and shy.
Nicholas had to go out to his truck to get some tools for the bedroom doorframe. I no longer cared what anyone thought of my fetishes. I was going to go after him!
While he went to his truck, I raced to my room and tore off my clothes. I threw on my fake tits chest piece. I put on a black lace pair of panties. I added a matching black lace teddy. Threw on a wig and as I was grabbing my black fishnet stockings and high heels I heard the door open. I raced to the bathroom and slammed the door. I heard Nicholas walk by and begin to pull his tools out of his bag. I quickly pulled up my stockings and strapped on my heels. Quickly spread some lipstick across my lips, gave myself a quick look over in the mirror. I took a deep breath, grabbed the door knob and panicked. Gave myself another look over, took an even bigger breath, and told myself that even if he laughs, and freaks out, I know I look good.
I shut off the bathroom light, slowly opened the door and stepped out into the hallway. He had his back to me and was only 5 feet away. I slowly approached him, pressed my fake tits against his back, wrapped my arms around him to his stomach and up to his chest. Nicholas jumped out of my arms, spun around and took 2 steps back.
“Holy shit! What are you doing?” He asked frantically
“From the second our eyes locked at Jo’s house last week, I’ve wanted you! I want you so bad!” I explained desperately
“I’m not gay!” He yelled
“Neither am I! My name is Stephanie. Let me take care of your loneliness.” I said as I slowly, seductively approached him.
I shut the bedroom door behind me before I let him answer or say anything so he knew that this was happening whether he wanted to or not.
“I admit we did have an immediate connection but this?! This is what you do?!” He asked
“I do this for guys like you.” I said as I untucked his shirt, slid my hands underneath and pulled it over his head and threw it on the floor, examining every one of his upper body muscles as my hand’s caressed their way up.
“Stephanie huh?” He asked as he put his hand on my cheek.
“Mmhmm.” I answered and then kissed him softly.
His strong arms wrapped around my waist and softly squeezed my ass. Our soft kissing turned into tongues dancing and drool. I felt his hard, increasing bulge pressing harder and harder against my stomach. It was very clear even with his pants on, sight unseen that his cock was huge!
My heart began to race as I knew how bad I wanted him but I knew that it was going to be something I wasn’t used to. I figured no sense in wasting time. If I was going to do this now was as good as any time.
I broke the seal our lips had formed with each other and nervously looked down at his jeans. I reached for the button and popped it open and unzipped them. Nicholas’ hands left my ass and started pulling his pants down. Still nervous of what I was getting myself into, or what was getting into myself I should say, haha. I buried my face in his chest hair and started kissing his chest muscles. As I felt his pants drop and hit the floor, he kicked them off and I felt his manhood hit my leg.
I reached around him and began squeezing his tight, muscled ass and slowly started kissing my way down his chest to his stomach. I had my eyes closed the whole time, I was so unbelievably nervous. I took a deep breath, told him to sit in the bed and I got on my knees between his legs.
I opened my eyes and his big hog was staring me straight in the face. Not only was his cock huge, and thick but it looked perfect! I have seen a lot of dicks via porn or guys I’ve blown or whatever, every dick is different and Nicholas had a perfect cock.
I grabbed the base of his shaft and wiggled a bit so I could get a really good look at it. It was no question between 9 and 10 inches. I was so scared and nervous but I said to myself I wasn’t going to chicken out. This is the first time I had ever thought a guy was hot and I wanted this man and it might be my only chance.
I opened my mouth and put his manhood inside. My tongue swirled the tip of his cock. He was definitely a mouthful as I couldn’t get much more than his head and little more in my mouth. Just when I think his cock couldn’t get any better, I realized how amazing he tasted and smelled. His cock tasted so fucking amazing! My sucking started to get much more intense now. I wanted him to cum in my mouth! I bet his cum tastes even better!
“Oh my god I want to fuck you Stephanie!” Nicholas said sitting forward and grabbing my arms and kissing me passionately.
“I want you so bad!” I moaned out with excitement that he called me Stephanie.
I pulled the lubricant from my dresser drawer, squirted a glob on the tip of his cock, slid my hand down to his shaft covering his dick completely. I squirted a little more in my hand and rubbed it on my ass hole and shoved two fingers up there to help with penetration.
I got on the bed on all four and felt Nicholas position himself behind me. My heart raced as I felt him press his cock against my eager hole. He pressed gently. I let out a little moan.
“Mmmm” I moaned
He pushed a little harder, I moaned a bit louder.
“You ok? Let me know if you’re not.” He said
“Mmmhmm.” I moaned. He cared.. I was in love. “Push it in me. I can take it.” I moaned out not really knowing if I could or not.
His hand grabbed ahold of my hip and his other grabbed hold of his shaft. He pulled my hip and pushed his cock inside me.
“Ahhhh! Oh god!” I yelled into my pillow
“Still good?” He asked
“Yes! God yes! Fuck me baby! Fuck me!!!” I cried out into my pillow.
Nicholas pushed his cock deeper and deeper inside me with each gentle thrust until he was all the way in. Balls deep! I felt him inside my stomach! My asshole was being stretched like never before. I had never been more turned on!
As Nicholas began to thrust more and more a huge fresh supply of cum unknowingly to me shot out of my cock and onto my sheets. His cock felt so amazing inside me and it was all I could think about that I didn’t even realize I came all over the place myself.
“I’m gonna cum so hard, Stephanie!” He grunted
“Do it! Cum for me! Cum inside me!” I yelled out
I had one final thrust and his hands squeezed my hips so hard that it left bruises. He let out a loud grunt and moan! My yells and moans matched his in volume. I felt his cock pulsing inside my hole and pumping squirt after squirt of cum deep inside me. I still didn’t know that I had came but it was already the best sex I had ever had, gay or straight.
As Nicholas released his grip on my hips and pulled his cock out, it felt insanely good as his cock slid out. Truthfully it felt like taking a huge shit. I instantly felt cum pouring out of my hole and dripping onto the bed and down my leg.
I was exhausted at this point and I collapsed on my side. I patted the bed hoping he’d lay next to me, but instead I felt his hand begin to play with my cock.
“Do you want me to take care of you now?” He asked stroking me more thoroughly now.
It was at that point that I looked down and realized I had already came all over the bed.
“You already did baby.” I said pointing. At the puddle of cum next to my knee.
Once again I patted the bed for him to lay next to me. He obliged and we just laid there catching our breath for a while.
“You don’t need anything fixed around the apartment do you?” He asked laughing a bit
I chuckled a bit, told him not at all and then started kissing him. Despite it only being early evening, we both dozed off in the bed together.
Nicholas woke up about an hour later and woke me up while playing with my fake tits chest piece.
“Excuse you mister!” I said jokingly
“This thing is a trip. It’s pretty convincing.” He explained “Hey, do you mind if I use your shower?” He added
“Of course.” I responded
As he began taking his shower I started taking off my lingerie and chest piece. I was a cum covered mess and I needed a shower as well.
I entered the steamy bathroom quietly and poked my head inside the shower curtain. Oh my god seeing the water trickle down Nicholas’ body was the single hottest thing I have ever seen. I don’t know what it was about this man that drove me so crazy!
“Room for one more?” I asked
“Of course.” He answered reaching his hand out and assisting me inside.
“Is it ok that I’m not Stephanie right now?” I asked
“We’ll I definitely prefer Stephanie but this is just fine as well.” He said with a smile and a quick kiss on the lips.
“Good because I have little unfinished business to handle.” I said
My unfinished business? I hadn’t tasted his cum! His cock tasted amazing and I wanted his cum in my mouth! So I slithered down his body and onto my knees and took his meat in my hands. I put it back in my mouth and started sucking him aggressively! I could still smell and taste the stench of our sex on his cock. My cock was rock hard as well.
I started stroking my cock vigorously. He started to moan and I could feel his cock swelling in my mouth. Nicholas placed his strong hand on the back of my head and shot a hot load of cum in my mouth! It hit the roof of my mouth and trickled down my throat. Another spurt hit my tongue and then a third and fourth! I couldn’t believe how much cum he produced after unloading in my ass less than 2 hours ago.
As I sucked the last little bit of cum from his dick I stroked my cock and shot a load on his foot and the shower mat.
His cock smelled and tasted amazing and his cum tasted unbelievable! Un-fucking-believable!!!!
I stood up and he didn’t hesitate to kiss me which made me happy.. he didn’t care that my mouth was just wrapped around his cock and full of his cum.
We exited the shower and he went home. I really wanted him to spend the night so I could get into some comfy pj’s and spend the night pleasuring him but he had to leave. We made plans to get together again a few days later…
I’ll tell that story next time
👄This will be the best oral sex you have ever experienced.👅