I was caught by my mom and suddenly all my secrets were out in the open.
Mom rolled her eyes, shook her head and closed the bathroom door.
“Clean this up and I’ll be waiting downstairs.” I heard her say as she headed downstairs
I did as she requested. I picked up the pile of her clothes off the floor, washed the makeup off my face and cleaned her dildo as best I could before making the slow and terrifying walk downstairs. Mom was sitting in her favorite chair staring at the wall.
“Sit down.” She mumbled as I entered the room
I’d like to say we had a long productive conversation but it was more of a lecture about how she had been treating me like the man of the house for 3 years and this is what I did behind her back. It was clear she was disappointed and that certainly made me feel guilty but the truth was I spent most of her lecture fantasizing about my date with John on Saturday.
After and hour or so of listening to her lecture me I agreed to her terms which were: if I was going to be the man of this house, I needed to act like a man. No more dressing in women’s clothes.
Oddly enough, I spent the night with my mom and we ended up having very awkward sex. I know what you’re thinking, any sexual act with your mother is awkward, but her and I had a thing going for over 3 years and by now it was completely normal to us. This was the first time it felt weird since the first time when I was 15.
The following morning I woke up and left as early as possible despite mom holding me to remind me of what we talked about and whether or not I wanted her to treat me like a man. I love my mom. More than anything in the world and it may be weird to some but we normalized our sexual relationship. Justifying it by telling ourselves that she was A. Treating me as the man of the house and B. Teaching me how to satisfy a woman. I was not going to give up what we had, but I wasn’t going to give up my other desires either. I had to come up with a plan to do both.
Fortunately for me my roommate at the dorm was pretty cool and liberal and I had hoped that maybe after talking to him, I could normalize my cross dressing around our dorm. At least in our room. But that was going to have to wait. I had a date with John tomorrow night and I was excited!
Saturday night came and I spent the entire day in the bathroom shaving my entire body. John didn’t mention anything about it, I just decided to do it. I figured if we were going to have sex, maybe he’d appreciate a smooth body. I also made sure to wear my favorite pair of panties I had. A black spandex thong that really made my ass look good. I also put on just a little bit of make up, not too much. As I made my way down the stairs to meet John I had panties, my long red hair, some make up and a perfectly smooth body. I felt really sexy but truth be told I probably looked a mess.
As I approached John who was waiting outside for me, he smiled and gave me a hug.
“You look very nice.” John said and then quickly kissed me.
We got in his car and he mentioned that we were going to dinner and another movie. Me being underage still, I couldn’t get into bars yet so movies were about all we could do.
We had a really nice conversation at dinner. It was a fairly fancy restaurant. During our conversation he asked about the makeup and I took the opportunity to tell him that I was a cross dresser. Even confessing I was wearing a thong. I felt embarrassed immediately after but John seemed like he liked it.
After dinner we went to the same movie theater we went to the weekend before. We whispered back and forth throughout the movie just as we did the previous date. I had never been more horny than I was that night. The entire night all I could think about was John’s dick. I wanted it inside me so bad!
“Why don’t you take your cock out?” I whispered to him
John gave me a look like he was impressed and then scanned the theater to see if we were being watched. As John pulled his dick out I spit in my hand and began stroking him. I watched him bite his lower lip to avoid making a sound.
“I’m going to cum.” John whispered to me
I pretended to drop something and got on the floor and pretended to look for it. What I really did was put his cock in my mouth! I was so horny and so fucking hot for him that I didn’t care if anyone saw me. As soon as my mouth wrapped around his cock he exploded down in my mouth! Hot cum came in waves down the back of my throat. John had a handful of my hair holding me in place and he unloaded inside me.
“I thought we’d wait for later for that, damn!” He mumbled to me as I made my way back into my seat.
“There’s more where that came from.” I answered
John and I immediately agreed we no longer cared about the movie and we quickly got up and left. We got to his car and started making out aggressively. Our hands were all over each other and our tongues were shoved down each other’s throats.
“Let’s go back to your place.” I said out of breath
John started his car and we sped off. He only lived about 2 miles from the theater and he drove so fast that we got there in less than 2 minutes. We kissed some more before we exited the car and then made our way up to his apartment.
John lived in a really expensive apartment. I still wasn’t sure exactly what he did for a living but whatever it was he was doing it well.
We kissed some more in his kitchen and he then lead me to his bedroom. I sat on the edge of his bed and didn’t hesitate to start undoing his belt and pants. He took a step back and pushed his pants to his ankles and kicked them towards his laundry basket. I grabbed firmly onto his cock and stuck it in my mouth. I could still taste the salty residue from his cum earlier. John ran his fingers through my long red hair as he guided my head back and forth up his shaft.
John and I both removed our shirts at the same time. He had a fantastic body with beautiful thick chest hair. It made my chubby body look terrible but I didn’t care at the moment. I started pulling my pants down leaving my thing on for him to see. John took my hand and stood me up and spun me around.
“Wow you have a great ass!” He said lustily
“Thank you.” I answered blushing a bit
John pressed his toned chest and stomach against my back. His rock hard cock sandwiched between us. His right reached around and into my panties. His hand squeezed and began stroking my cock. His left hand reached around and groped my chest and pinched my nipple. I was chubby enough that I did have small boobs. John kissed and nibbled on my neck. I felt so fucking turned on!
“I want you so bad!” John grunted
“Take me then!” I answered passionately
John reached over and grabbed some lubricant from his dresser drawer. He pulled down my panties and pushed me onto the bed. I landed on my stomach but quickly popped up onto all fours. I gave him a wiggle of my ass and smacked it afterwards. John leaned down and began milking my cock like an utter. Suddenly I felt his tongue circling my asshole. Oh my God that felt so incredible! I had no clue that was a thing at the time and after he licked my ass I was in love with him, lol. Unlike anything I had ever felt!
Then the moment of truth. John pressed his freshly lubricated cock against my eager hole and pushed. He knew what he was doing because he got the tip in very quickly and then just held it there until I relaxed. I let out a yelp. It hurt but I wasn’t about to say anything.
The first thing I noticed different from a dildo vs a man was that I had control of the dildo. I did NOT have control of John’s cock… and I loved that!
John started to softly thrust himself in and out and I relaxed instantly. Within 30 seconds John was balls deep in my ass thrusting him manhood deeper and deeper inside me! I buried my face in his pillow, screaming! There was just the slightest bit of pain but there was the most massive bit of pleasure in it. Every time his cock slide back inside me it rubbed that prostate and I felt like I was going to explode! I seriously thought I was going to pass out from it!
John had just cum less than 20 minutes ago in the movie theater so he was able to last for almost a half hour. He fucked me doggystyle for most of that time! John finally pulled his cock from my ass and rolled me onto my back. He lifted my legs and put them on his shoulders. Slid his cock back inside my loosened hole. Sweat dripped from his nose and onto my stomach and he resumed fucking me. This position felt like he was going even deeper. I had to grab his pillow and bite down on it to avoid waking his neighbors.
“Ooooh shit I’m gonna cum!” He growled
John finally pulled his cock from my ass. My legs fell down on either side of him. He squeezed the base of his shaft and stood up on the bed.
“Sit up!” He demanded.
I did as he asked and sat up. With clinched teeth John pointed his cock at me and released his manly grip from his shaft and began stroking himself. Suddenly 3 quick spurts of hot come hit me. The first on my cheek, the second my nose and the third on my tongue. I quickly swallowed it and opened my mouth again. John pressed the tip of his cock on the tip of my tongue and released a few more smaller drops of cum. I reached up and squeezed his cock and licked the head a for a few seconds sucking out the last few bits of cum I could get from him.
John and I laid next to each other sweaty and out of breath. Neither of us spoke. We were too tired to formulate a coherent sentence anyways.
We both fell asleep without getting up to clean ourselves or even turn off the lights. I woke up once in the night and the lights were off now and John was spooning me. I think I know what woke me up. John was sleeping but he was rock hard! I wanted to reach back there and stroke him but he was pressed pretty tight up against me. I had a difficult time falling back asleep so I laid there a while thinking about how awesome it felt when John fucked me. I never knew that side of sex and it was unbelievable!
I finally did fall back asleep and eventually woke up to John kissing my neck and back. I wiped the sleep crud out of my eyes and rolled over to face him. John and I kissed a few times and made small talk about how we slept. I didn’t mention anything about his midnight erection. We kissed and some light tongue kissing before John asked me if I wanted to take a shower before he took me home. I excitedly agreed.
John and I climbed into the shower and the hot water started cascading down our bodies. We immediately began making out much more intensely.
“You gonna fuck me again or what?” I jested
John spun me around and pressed my face against the wall bending me over in the process. Pressed his dick against my hole and pushed his way inside me once again! I moaned as it slid inside. John grabbed ahold of my hips and started pushing his manhood inside me.
As he plunged his cock in and out of me I began thinking about my mom and how she taught me how to pleasure a woman but also by doing so, she kind of taught me how a man is supposed to be treated. Even though he was being much more aggressive than the night before and despite it hurting this time I pretended to enjoy it for him. I wanted him to get his nut more than I cared about myself right then.
John made a final push to the finish picking up the intensity. Then with one final thrust he clinched his teeth and pushed his hips into me. His hands squeezed my chubby hips so tightly he left nail marks. John let out a primal moan. I felt his cock pulsing as I squeezed my sphincter around it. John pulled his cock from me. I felt his cum leaking from my ass and dripping into the shower. Even though he pulled his dick out of me, he didn’t let go of my hips for a few seconds.
I stood up and was light headed for a second or two. As I turned around to face John he looked spent. He looked satisfied! For that moment I think I knew what my mom felt when her and I were with each other. She took pleasure in me being treated like a man just like I was taking pleasure in seeing John fully satisfied.
We did eventually clean ourselves and got dried off and dressed. John took me back to my dorm and kissed me before I got out of the car. I had to call in sick to work the next day because my ass was sore. You’d think that would make me reconsider this but all it did was remind me of the night before. At the time that was the best I had ever felt sexually. It was definitely a feeling I had never experienced or imagined.
When I got to my dorm room my roommate asked about John. I confessed I was with him and he put 2 and 2 together.
“Dude, did you have sex with that guy?!” My roommate asked
“Yeah.” I said shamefully “…TWICE!” I added jokingly
“I work with his WIFE! I know that guy! He’s not gay!” He raised his voice.
“What?!” I said confused…
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