My Life Pt. 05: Paul

My Mom and Paul

Those of you who have been reading my stories know that I have a fascination with my Mom and her sexuality. My Mom is a gorgeous Italian woman. She is very voluptuous with big breasts and nice hips. She has long curly dark hair like mine and hazel eyes. Her skin is the loveliest olive shade I have ever seen on a human being, though I may be a bit biased.

Yes I fantasized about being with my Mom. She has even expressed a certain level of attraction for me and she does read all of my stories. We've never had sex though; it's a line we aren't willing to cross, mostly because we both value our relationship too much. The following story is the closest we ever actually came to doing it.

When I was 19 my Mom started dating this guy, his name was Paul. He was in his mid-50s and had the sexiest salt and pepper hair. He was very tall, about six foot four I think and had a hair chest and a very nice athletic build and was in great shape for his age.

Paul and my Mom were super sexually active. I was no stranger to my Mom's sexuality at this point. Something about her nature and the fact that she had a transsexual daughter led to an air of openness. She'd been with a number of Men since my father left us and she even had an occasional girlfriend. Our house was a very liberal one and sex was not a topic we shied away from.

I would hear my Mom and Paul going at it all the time. I was really attracted to Paul too, but he was my Mom's boyfriend and I respected that boundary. Still I couldn't help dressing sexy and flaunting my body around the house. He was so hot and I liked him so much I totally couldn't help flirting with him constantly, which my Mom thought was hilarious and teased me about.

I had recently broken up with John, my first boyfriend and I was a bit sensitive. I think that is why my Mom was so relaxed about my flirting.

Paul knew that I was transsexual that I was born a boy but had transitioned to female when I was a young teen. He also knew that I have a penis because again, it was an open house and we all talked about a lot of things. He accepted me for who I am and he genuinely seemed to enjoy being around me. That's not true for everyone; in fact it is kind of rare.

I am a passable girl and people are often attracted to me. I'm almost the opposite of my Mom in a lot of ways, where she is extremely curvy, I have more of a lithe body with long legs, nice but narrow hips and small breasts. I share my hair and skin tone with my Mom.

The sad truth about being Trans is that when a lot of people find out about me, particularly if they are attracted to me, they often become uncomfortable with their own attraction. For some reason I will never understand trans people make some people really uncomfortable. It makes me feel sad sometimes, I am a person like anyone else, but hey you can't please everyone right? Paul was definitely comfortable with me though, that by itself was a huge turn on for me.

I have to confess that did start thinking of him as a surrogate Dad after about their second month of dating. My Mom usually didn't date people that long so it was a unique situation for me. I do also kinda have some "Daddy Issues" because my real father was an abusive asshole who left us over how I am. He expected a manly son. He treated me very badly.

Anyway Paul and I had developed sort of a playful relationship. He'd tickle or pinch me and I'd slap him and we'd chase each other around the house, you know, just silly stuff. We'd wrestle sometimes and I knew he was attracted to me because I could feel him get hard sometimes when we'd roughhouse. Sometimes we'd both get really turned on, then he'd drag my Mom into the bedroom for some fun and I'd run off to my bedroom to take care of myself while listening to them go at it.

To answer the obvious question at this point, my Mom was well aware of all of this happening and she never seemed to mind where Paul got his sexual energy from as long as she had a good time in the process.

So how it all happened was on a Friday night we were all snuggled on the couch watching some lame movie and Paul kept messing with me.

"Hey! Stop it!" I yelled when he tickled me.

He started to poke me in the ribs and I'd wiggle away and playfully slap him. This devolved throughout the movie to a full on play fight. I somehow ended up straddling his lap, I could feel his cock growing beneath me and I was getting hard too. It was going to be another one of those nights!

Then he pinched my nipple through my shirt really hard, which made me squeal and slap his face equally hard. That stopped us both for a second and we looked at my Mom because she'd usually tell us to knock it off if things got too rowdy.

She was looking at us weirdly and biting her bottom lip. She was still covered in the blanket we had all been under a few minutes earlier. "You two should do it." she finally said. Our jaws must have both been on the floor. I think we both thought that our slap and tickle relationship was just that and never expected it to go any further.

"Do what?" Paul asked.

"Fuck" my Mom replied with a seriously horny and over the edge look in her eye.

"You can't be serious?" Paul asked again.

My Mom just nodded her head in response, still biting her lower lip.

We were floored, Paul and I just stared at her unbelieving. It seemed like a joke, it must have been a joke, but her look was so serious.

We kept expecting her to say "Nah just kidding." any second. Instead she pushed the blanket off of her to reveal that her other hand was down the front of the shorts she was wearing. She was masturbating while watching us wrestle.

Everything moved pretty fast at that point. Paul and I looked at each other for a second and then we were making out really intensely. I was moaning into his mouth.

"Oh fuck yes." my Mom said in encouragement.

His hands went up my shirt to squeeze and play with my tits; I was grinding my hips rhythmically against his now raging hard cock as our tongues swirled together. Paul and I were both moaning as we made out. My Mom let out a long low moan, watching.

I wasn't wearing much, just a pair of panties and an oversized t-shirt, which Paul ripped in the process of getting over my head and off. I'm glad it wasn't one of my favorite t-shirts.

I was trying to pull his cock out of his PJ's and everything was really frantic and hot. I jumped off of his lap and started yanking down his PJ bottoms until they were around his ankles. Then I was on my knees sucking him deep and fast, he was groaning and thrusting into my wet hot mouth. His cock was gorgeous! It was long, straight and thick. There was no foreplay here, the foreplay had been happening for months now, this was an explosion of pent up sexual tension.

"Oh fuck that's so hot Baby," my Mom said.

"Mmmhmmm" I replied with my mouth full of Paul's cock.

"Oh wow Baby, you are so fucking sexy!" she replied.

Paul was getting close when he heard my Mom encouraging me and pushed me off of him. Fuck! I was hungry for his cum in my mouth, but he kept me away, calming down for a second. Then he stood and stepped out of his PJs. He roughly grabbed my arm and threw me over the arm of the couch facing my Mom who was rubbing her clit in slow circles in her shorts. Her other hand exposed one of her massive tits and was pinching and playing with her large dark nipple.

Paul yanked my panties down, ripping them too, and buried his face in my ass, his tongue fucking my tight little hole and getting it all wet. I moaned and ground myself against his tongue, no one had ever done that to me before! Then stood behind me and I could feel his hot raging cock between my cheeks.

"Is this what you want?" he asked my Mom. I noticed he didn't bother to ask me.

"Do it, fuck her." she said.

Then he was pushing himself inside of me. He was big and saliva really isn't the best lube in the world, it hurt, but in such an intensely sexual way I didn't want it to ever stop. My little girl cock was pressed into the arm of the couch and felt like it would explode any minute.

"Mommy!" I cried out, tears streaming down my face, "He's so big Mommy"

"Yes Baby!" she moaned rubbing her clit furiously now "Oh yes, take it baby, take it all!"

He started fucking me really hard. Finally the pain was turning into pure pleasure. I reached out to brace myself from his pounding and grabbed my Mom's ankle.

The second I touched her and my fingernails dug into her skin my Mom's hips started bucking and her body shuddering. Watching my Mom orgasm was too much for me. Paul's hips were slapping my ass as he fucked me, pounding my ass as my girl cock was pressed into the couch arm with every thrust. He was grunting and pounding me hard.

I could hold back no longer. I came so hard, body shaking, my Mom and I both moaning unintelligible sounds. I could feel the warmth of my hot cum on the leather couch making it slippery beneath me. Paul thrust deep inside me three or four more times when he grunted loud and buried himself deep inside me. I could feel his cock pulsing in my ass as he filled me with his cum.

That was the closest we ever came to a threesome and the closest my Mom and I ever came to having actual sex.

After that Paul would sometimes come up to my room in the night and climb in bed with me when my Mom wasn't in the mood, which wasn't too often. Paul lived with us for a few more months and sometimes I would give him head before he left for work. He liked that a lot and my Mom isn't a morning person. I was always happy to help.

So what happened to Paul? He got too needy after a while. He wasn't the jealous sort when they started dating, but he developed a jealously that Mom and I just weren't going to put up with. So we eventually had to have him out of our lives. The breakup was hard, but for the best.

A couple of years later I ran into him at the mall. We ended up fucking for a couple of weeks before he misbehaved and I had to have him out of my life for good, but that is another story. Even though the end wasn't great, I will always remember him fondly.