I got stretched Pt. III

Getting fucked my a strap on is great but I missed the real thing.

My fiancé and I were having a very liberating sex life. I was able to be myself or my other self, Stephanie. It also allowed Ashley to have another side, Andy, she called herself.

Our apartment was being debugged because of a roach problem so instead of putting up with the bug problem, I just moved back home temporarily with my mom. Ashley temporarily moved back in with her parents as well so we were apart for a while which sucked for sure.

Feeling liberated I finally took the time to tell my mom about my other self. I told her just about everything! I told her about my first homosexual relationship with my friend Jayson and how we fooled around for years before he finally let me fuck his ass.

I told her about Jo, the guy that I let fuck me and started my crossdressing. How I love wearing women’s clothes and and feeling like a woman. My mom wasn’t surprised at all, to my shock. My fascination with my mom sexuality is probably where all this started. I adored my mom, both as a mother and a sexual fantasy. When my dad left, she started dating and when she’d bring home men from the bar, I’d always listen and spy on them having sex. Even after she found out I was doing it. In fact, she’d leave the door unlocked or cracked open a bit so I could watch. She was turned on by me watching, but that’s all a different story for a different time.

Long story short, mom was completely cool with me being bisexual and crossdressing. It made me feel so great knowing that I finally found a woman that accepted me, and my mom did the same.

About a month after I moved back in, my mom was out celebrating her 51st birthday with some friends. Ashley was out with some friends at a concert as well and I had a Saturday night all to myself. Since I had some alone time, and I hadn’t had sex with Ashley in almost a month. We didn’t have a lot of time alone together now that we were both living at home. I decided I was going to go all out with my masturbation this night.

I drew myself a bath and grabbed my favorite dildo, a 7” realistic feeling dick with a suction cup on the bottom. I stuck it to the bathtub and rode it until I came hands free! Afterwards I got out, brushed my hair, I had been growing it long now and it was past my shoulders. I put some scented lotion on that my mom had, went to my room and put on some satin panties and a matching nightgown that went half way down my thighs. I had just bought this and was dying to wear it to bed!

After about 15 minutes of lying in bed, I heard my mom come home. So I got out of bed and opened my door, but I heard more than my mom’s voice. She had brought a man home and she sounded a bit drunk. It didn’t take them long before they moved to her bedroom.

Curious as I am, and wearing my sexy new nightgown, I was still a bit horny so I slowly crept out into the hallway and made my way towards my moms bedroom. I heard them making sexual noises but when I tried to open the door a crack, it was locked. I still stood outside her bedroom and listened to them fuck, stroking my cock the entire time.

I had listened to my mom have sex many times and I knew she was a screamer, and I knew when she was enjoying it and when she wasn’t. She was definitely enjoying herself! She was talking dirty and making little whimpering squeaks that she didn’t make when the guy she was with was doing a bad job.

Just before they finished, I came in my hand. I took the opportunity to taste cum for the first time in a while so I licked my hand clean. It was hot, and it turned me on more! I went back to my room to lay down and day dream of dick!

About 20 minutes or so went by when I heard footsteps outside my door and down the stairs. I got out of bed, threw my bathrobe on, and headed downstairs. I assumed my mom was the one in the kitchen but I was wrong. It was the man my mom was with. I stopped short of the kitchen and watched him for a minute before he saw me. He was an older guy, around my moms age. He had salt and pepper semi curly hair. He was impressively built, nice chest muscles and arms. Thick curly chest hair, and a black mustache. A real man’s man looking kind of guy. Certainly not my type but seeing him standing there in our kitchen in just his underwear, chest still gleaming with sweat, he looked gorgeous at that moment. Plus, I could see his bulge was impressive and I just heard him give it to my mom well and good!

I quietly entered the kitchen as he had his back to me. I saw a tattoo on his back of a cattle skull.

“Hey there.” I said in the most subtly seductive voice I could do.

He turned as if I startled him, and he looked shocked when he saw it wasn’t my mom.

“Who are you?” He asked “oh, wait you must be the son she’s been talking about all night.” He quickly added before I could answer.

“That’s me.” I finally responded “where’s my mom?”

“Passed out. Ain’t that robe a little girly for you?” He asked quite boldly

“Want me to take it off?” I asked flirting big time now.

He didn’t answer but he did give me a look down from top to bottom and I took that as a “yes”. I untied the robe, opened it up and dropped it to the floor.

“Whoa!” He said as he took a step back. “What’s going on here?”

I had no idea how to actually seduce a man, I only knew what I saw in porn and what I’d fantasize a woman would say to me so I just blurted out the first thing I thought.

“I’m just a girl trying to get a nut.” I said immediately regretting it. It was so stupid but I couldn’t let him see my embarrassment.

“I thought you were a boy?” He asked

“I can be whatever you want me to be.” I answered with a smile taking a step closer to him. We were now just a foot apart. I reached out and ran my fingers thru his chest hair. It made my cock so hard! “What do you want me to be?” I asked

“To be honest, I’m not totally opposed to what I think your proposing but I’m into chicks.” He said a little shy and uncomfortable but not pushing my hand away

“I said, I can be whatever you want me to be.” I said

I glanced down and noticed his bulge was growing as my hand continued to stroke his chest hair. I knew he was getting turned on but I felt he needed more convincing.

“I’m gonna go get ready, if you want to join me, I’ll leave my door unlocked. Come by in an hour”. I said

As I bent down to pick up my bathrobe, I saw his cock was hard now. I reached out with just my index finger and ran it across his hard cock and stood up, smiled and bit my bottom lip and turned and went back to my room.

After I took a quick shower only to shave all my legs and pits, I had 30 minutes to get ready so I hurried and grabbed a pair of white silk stockings and my black high heels and put them on. I slid a pair of white lace panties up my smooth legs. Ashley had bought me a new fake chest piece that had smaller tits on it. The one I bought a couple years ago was ludicrously big. This new one was much more real looking and made me much more “passable”. They were cute little B cups that I loved! They fit my figure perfectly and made me feel like a woman and less like a crossdresser.

The chest piece was a little tighter and harder to get on but once I did I had noticed time running out. I quickly thru on some lipstick and a little eye makeup. Nothing special just a little eye shadow and eye liner. I put on a cute tight little black dress on. I began to brush my hair and quickly make it as feminine looking as I could in the little time I had.

It had been an hour. I kept my door unlocked and stood in the middle of my room with the lights on waiting. A few minutes passed and it was now over an hour. Normally I wouldn’t be disappointed because I still got to dress up and not gonna lie, I looked amazing. My new tits looked perfect on my thin frame. This time I would be disappointed if he didn’t show, because as I admired myself in the mirror, I realized I just got this hot in an hours time.

Suddenly I hear footsteps and then a light tapping on my door. Then the door cracked open and the man’s head popped in.

“Holy shit!” He whispered as he fully entered my room and closed the door. “You look incredible!” He whispered some more.

“I told you I can be whatever you want me to be. And you don’t have to whisper, moms a sound sleeper.” I explained as I approached him.

I grabbed a hold of his hand and locked my door before leading him towards the bed. As we got to the bed, I turned him towards me, ran my hands up his stomach to his chest and ran my fingers thru his chest hair once more. Then I kissed him on his clavicle and made my way to his neck. My hands worked their way around his waist and slid inside his underwear and squeezed his ass. For a man in his 50’s he had a great ass! He began to loosen up a bit and he put his hands on my hips. I gave his ass a good squeeze and then pushed his tighty whiteys down to his ankles. I felt his cock flop out and poke me in the stomach. It was enough for him to hike my dress up above my hips and he worked up the nerve to reach in the back of my panties and squeeze my ass in return.

I couldn’t wait any longer, I wanted his cock! I got down on my knees and grabbed a hold of his 8” dong. Squeezing the base of his shaft I took the tip in my mouth and slid my lips as far down as I could. He let out a gasp of relief as I felt his entire body relax.

My lips slid up and down his shaft and my tongue swirled around the head of his impressive dick. I could taste small amounts of precum start to leak from his cock.

I stood up, pulled the straps of my dress off my shoulders revealing my cute little titties! He cupped them both and even leaned down and kissed and licked one of my nipples. I moaned to keep the fantasy alive. I leaned in and kissed him on the lips. I shoved my tongue in his mouth. His mustache made me do it! I had never kissed a man with a mustache before, so I just had to do it! His manly mustache tickled my upper lip and nose, and for some reason, it turned me on so much! It was so sexy being with a much older, manly man! He was making me feel like a woman and I loved it, and I didn’t even know his name!

I placed my hand against his rugged chest hair and pushed him on my bed. He landed on his back and put his hands behind his head and interlocking his fingers in a very relaxed position. I slid my panties down to my thighs and shimmied them down to my ankles.

“Wow!” He said

“What?”

“You’re packing some heat there!” He said looking at my rock hard cock. “May I?” He asked sitting up and pointing at my stiff cock.

“You can do whatever you want to me! I’m all yours!” I told him.

He reached out and grabbed my cock. He stroked it a few times. He began to look uncomfortable and unsure.

“You ok?” I asked

He didn’t answer. Instead he opened his mouth and stuck out his tongue. He lightly licked the tip of my cock and then kissed it. Then he looked up at me, and looked back down at my dong and put it in his mouth. He awkwardly slid his mouth up and down on my cock and an occasional tongue and even more occasional tooth. I stood there pretending to enjoy it for a minute or two and then pulled away. I leaned down and kissed him and again pushed him on his back.

I grabbed the lubricant from my dresser drawer and squeezed a bunch in my hand. I stroked his cock with it and ran my hand up my ass crack wiping the remaining lube on my hole, even shoving a finger up my ass getting it all over!

I straddled him and grabbed hold of his shaft and pressed it against my eager asshole. Pushed down a bit, then a bit more and *pop* the head of his big cock slid in my ass!

“Oh fuck! That’s awesome!” I moaned out as he let out a grunt!

I started to rock back and forth as my hole loosened up his cock slid deeper and deeper inside me. Eventually I sat all the way down and this man, who I didn’t even know an hour ago and still didn’t know his name was now a full 8” inside me!

I began to ride him harder and faster with each passing second. I couldn’t believe he hadn’t cum yet! I had been riding him now for almost 10 minutes. Suddenly I felt like I had to cum! Before I could reach down and grab my cock I started shooting spurts all over his stomach and chest hair!

“Oh fuck I’m cumming!!” I blurted out louder than I wanted to

“Wow!” Is all he could say as he looked down at my cock shooting spurts of hot cum every where.

I sat up a bit and started stroking my cock. As I did, his cock slid out of my ass. I shot the remaining drops of cum all over his chest. I leaned down and started licking up my cum from his manly chest hair.

“Damn, you’re a kinky slut!” He muttered in surprise as I cleaned up his chest hair of cum and sweat!

“For you I am! You need to fuck me some more!” I demanded

I climbed off him and he sat up and positioned himself behind me doggystyle. He pushed my face into my pillow and plunged his cock back inside my sweaty, wet boy pussy. I was so loose and stretched that I barely felt a thing as he thrusted back inside me. His hands grabbed my hips as tight as he could and my hands did the same to my pillow. He began to pound my ass like no one ever has. It was the roughest fucking I ever had. My hands gripped the edge of my bed as I screamed into my pillow. It hurt a bit but felt so amazing to be so completely dominated by this big hunk of a man!

He continued to fuck my ass for another 5 minutes before letting out a loud grunt.

“I’m gonna cum so hard!” He grunted barley understandable

“I want your cum!” I cried out

He pulled his cock out of my ass and squeezed off the base of his shaft. I turned to see what he was doing and he grabbed my head and pulled it toward his cock. I knew he wanted to cum in my mouth now. I had never done an ass to mouth, not afraid to, just never did it. This time I had no choice. He was dominating me and forcing me to. I opened my mouth expecting a shot of hot cum but he shoved his cock in my mouth! I thought my ass would taste worse than it did but I guess that shower before helped.

I started sucking his cock and not worrying about where it just was, and as he released his grip on his shaft, a huge spurt of cum shot inside my mouth and down the back of my throat. I gagged a bit as I wasn’t expecting that much cum but had to regain my composure as a second and third spurt did the same. I couldn’t believe how much cum was in my mouth! I was able to start swallowing now and I began to suck the last drops he had out of his balls.

Afterwards he left my room and I began to clean up. I was a hot sweaty mess! But, a hot sweaty, satisfied mess! Having sex with Ashley was great but nothing beats a real cock as opposed to a strap on. Having real cum shoot in your mouth, having a real cock stretch your ass and a real man behind you making you his little fuck toy is so much different… I just hope that Ash would understand….

The next morning I woke up and my ass was sore. I slept well in my new nightgown and panties. The exhaustion from getting my brains fucked out helped as well. I opened my door and a noticed a small piece of paper fall to the ground. It said “Hey, here’s my number… -Jim”

Wow, he even had a manly name! I had only been awake for a matter of minutes and already I was dreaming of him again! I immediately texted him. “That was the best I’ve ever had! Call me anytime! -Stephanie”

As I went downstairs my mom was sitting at the breakfast table drinking coffee. She stopped cold and stared at me for a minute. Almost forgetting that I was only wearing a silk nightgown and satin panties, I gave her a look as well.

“Oh shit! Forgot I was dressed like this.” I said

“It’s okay! I know about it, now I’ve seen it. If you keep hiding who you are, you’ll never be happy in life. Be who you are, always!” She explained

I gave her a kiss on the cheek which in and of itself would normally send feelings down to my dick, but again, that’s a story for a different time. I could smell Jim’s cologne on her.

“Who am I having coffee with?” She asked as she took a sip of coffee.

“I call myself Stephanie.” I answered “..that’s what you were gonna name me if I was girl right?”

“Yep.” She said smiling. “Again, don’t be ashamed of who you are, who you sleep with and how you do it. You don’t have to be ashamed around me. Not with our history.” She explained again.

“I know. I won’t. I’m comfortable like this. In women’s clothes.” I took a sip of coffee. “It just feels right sometimes.” I confessed

“Did I wake you last night?” Mom asked

“No I was up when you got home.” I told her

“Did you hear us?” She asked peeking out from her cup

“Of course, you know me.” I answered. A few seconds of awkward silence passed. “Did you hear us?” I boldly blurted out.

“WHAT?! You and JIM?! WHEN?!” Was I sleeping?! What the hells wrong with you?!” She yelled

“I’m sorry, I couldn’t help myself! I saw him in the kitchen and I thought it was you. Then I saw him and one thing just lead to another.” I explained embarrassed

More silence passed that was just awkward as fuck but then my mom just let her guard down.

“Was it good?” She asked me eventually

“Honestly?.. the best I’ve ever had.” I confessed. “..I’m a little sore though.” I replied

“Same here.” Mom said with a small laugh. “I’m seeing him again next weekend. Should I assume we’re sharing him now?”

“I’m sure we can come up with some kind of an arrangement that works for both of us.” I answered

“Oh boy…” she mumbled as she got up from the table and left…

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:

(average: 4.60 out of 10 votes)