Wed. Aug 17th, 2022

My name is James, I am 44yrs old,
I have enjoyed dressing up in women’s clothing since I was a teen. I was raised in a home with just my mom and older sister. Whenever I was alone I would sneak into my mothers bedroom, pick out a sexy outfit and transform into Jaime, my female persona. I was now 18yrs old.
One early Saturday my mother and sister headed out shopping, as soon as I heard the car leave, I locked the front door and I headed to mothers room to dress up like a little slut and masturbate. First I stopped in the washroom and shaved my cock and legs getting aroused with each task, then continued to Mom’s room.
I chose a pair of 5 inch white heels, white stockings, red panties, red bra, and black leather micro skirt from her wide array of clothing.
Once I was dressed I sat down at her vanity and applied some foundation, eyeshadow, lipstick, blush, and painted my nails a shade of deep red. I had very feminine features including blonde hair well past my shoulders.
I then proceeded to pose and show off my slim sexy figure in front of her full length mirror, I loved the way these clothes showed off my tight bubble butt, long shapely legs, and the slight bulge in the front of her panties. I was so turned on I laid on the floor beside her bed and started caressing my body, as I was playing I caught a glimpse of something intriguing under her bed, I reached way back and was delighted to find a large pink 7-8 inch rubber vibrating dildo.
This was new territory for me, I had never used a sex toy prior to this, the most I had done was inserting a finger or two up my tight virgin ass. I examined the toy with delight, I noticed there was something on the toy and when I inspected it closer realized it was my mothers dried up pussy juices, I smelled it deeply and could smell rubber and a faint pussy odor, I licked it and sucked it until it was 100% cleaned and glistening with saliva, my small cock was ready to fucking burst through the thin, delicate material I was wearing.
I positioned myself in front of the mirror, I put the toy directly under my ass and grinded on top of it feeling the thin layer of silk from her panties rubbing the outside of my tight asshole, this had my cock leaking precum as I gyrated the head of it against my sensitive hole. Without pause I pulled the panties to the side and used some spit to make it slippery, I sat myself down slowly, feeling this fake cock pushing slowly into my virgin ass. After a few minutes I came to the conclusion that if I was to get this rubber cock inside my asshole I was going to need some lubrication, I stood up and headed to the bathroom and found a bottle of baby oil, I took this back to my spot I front of the mirror and removed her panties that had a big wet spot on the front from my cock oozing precum, then proceeded to cover my asshole and the dildo with oil, now I was in fucking business!
I positioned myself so I could see the dildo sticking straight up towards my ass and lowered myself very slowly on to the tip, it was larger than I anticipated, it took me several realignments to get it perfectly aimed, I could feel it stretching me and it was a little painful so I added more lube and fingered my asshole for a few minutes feeling myself loosening up I tried again and this time I was able to squat down enough to get the head of the toy past my sphincter muscles, my fucking cock was as hard as steel by this time and I just rocked back and forth feeling it enter me inch by inch until my tiny ass was almost touching the floor, I had never felt this horny in my entire existence, I slowly started riding up and down feeling the cock filling my tight boy pussy. Within minutes I was furiously bouncing on the dildo while jacking my cock and watching this large fake cock disappearing inside of me. I then took it a step farther by clicking the little silver button located on the bottom of the toy, the vibrations engulfed me, I set it on medium and felt my sphincter muscles spasming, this was sure to make me prematurely explode.
I slowed my pace and was lost in escasty, I let go of my throbbing cock and just rode slowly up and down watching precum drip out of my now half hard cock.
I was very close, fucking my ass deep, and on the edge of spraying my cum all over the carpet when I heard a car door slam outside!
I stood up letting the plastic cock slip out of my now well lubed and stretched out ass and ran to the window, fuck it was my mom’s boyfriend Wayne.
I panicked, there was no way I could answer the door like this so I ran to my room and dove under the blankets.
He proceed to knock for a few moments and then stopped, oh how I wanted him to go away, I was scared shitless. Then my fears came to light as I heard the backdoor close! He must have known we never locked the back porch door. He yelled upstairs for my mother and when he got no reply he started up the stairs, I was trembling, my cock was still twitching, my asshole was still dripping, and I was wearing my mom’s sexy stuff, then the real panic kicked in as I remembered I had left the dildo, discarded panties with precum, and baby oil on the bedroom floor! I was on the verge of tears when I heard a light knock at my door. I answered “Hi Wayne, moms gone out shopping with my sister”. He proceed to open my door and ask how my day was going (if he only knew what I had on beneath these blankets), I replied fine but that I was tired from staying up late the previous evening. He told me to tell my mom he popped by for a visit and would call her later. I was so relieved when he closed my door and left. I stayed in bed for several minutes and was waiting for him to leave so I could continue my session. It was then I heard another light knock at my door, “hey you still awake” was the question, I muttered a quiet sleepy yes and Wayne reopened my bedroom door and was holding the plastic cock, panties, and oil in his hand with a subtle smirk on his face.
“What in the fuck were you doing? ” he asked, I had no answer. I stammered out something like “Why, what do you mean?”
He held up the panties with my precum stain on the front, the rubber cock glistening with baby oil, and the bottle of baby oil and said “Is there something you wanna tell me?”, I swiftly responded NO, and asked him to leave me alone.
Wayne then reached down a jerked the blankets, I held onto my end for dear life but lost the battle, I was exposed.
There I was dressed and shaking in skimpy women’s lingerie with my cock, balls and ass shiny from the oil I had used on them, Wayne sat down on the end of my bed and proceed to inform me he was going to have to tell my mother what he found me doing today, I begged, cried, and pleaded with him to not expose my crossdressing and masturbation to my mother. He placed the dildo and other naughty items on the bed and then put a hand on my ankle saying “there might be a way to keep her from finding out”, now I was petrified, I said I would do anything just don’t tell my mom…PLEASE!
We talked for awhile, with him asking why I dressed up? What I was doing with the toy? How often did I do this? I was scared and told him everything, he seemed very accepting and I started to get the sense that he was not angry.
I asked Wayne again to please not say anything to my mother, he replied that he wouldn’t and that’s when things got weirder.
Wayne asked me to show him what I was doing before he interrupted me, there was no way I could do that with someone watching and told him absolutely not, he then replied “It would be a shame to see your mother upset”. I was fucked, if I said no to Wayne my mom was surely going to find out her precious son was a perverted crossdresser, if I did what was asked I would never live down the shame of seeing Wayne again….
I made my choice, I reached down the bed and grasped the bottle of oil and squeezed a little into my hand, I proceeded to rub my balls and limp cock for several minutes, I was so nervous and scared with Wayne watching I did not get aroused at all.
Wayne then asked how I was using the dildo, now I was petrified again, I told him I just rubbed my cock on it. He asked if I would show him, so I proceeded to hold the toy and my cock in one hand and started stroking, again this did nothing for me sexually until Wayne reached up and pressed the silver button making the toy vibrate against my cock.
Now I was getting hard again, but now it was bashfully, and embarrassingly.
My cock was standing at attention due to the vibrations and I could not hide my pleasure from him, Wayne then shocked me by pulling out his cock and slowly rubbing my mothers panties that were sticky with oil and precum against his 7 inch uncut cock!
I couldn’t take my eyes off his throbbing cock, he went from semi-hard to fully erect in seconds. He then started to rub my lower calves and ankles gently, pausing every few seconds to simply watch. Wayne then pointed at the dildo in my fist and asked if I had ever tried a real cock, my response was a quiet “no”.
I was extremely fucking aroused by this time and was letting the toy slip between my legs down towards my asshole, I figured what the hell did I have to lose now, so I grabbed some more oil, stroked the plastic cock a few times and got up onto my knees carefully aligning the tip with my ass, it went into to me much easier this time, sliding halfway into my asshole in one thrust! Within minutes I was gyrating and riding that toy while stroking my teenage cock, Wayne seemed to love this as he slid halfway up the bed, he then reached for my swollen prick, I almost pulled away but was way to fucking horny to stop this act.
Wayne stroked my cock slowly (and his own) while I rode myself into oblivion, he then reached under me and pressed the silver button again engaging the dildo into the HIGH setting.
Upon feeling the intensity of the highest setting my eyes rolled back into my head and my cock erupted, huge globs of cum spurted out all over Wayne’s hand and the bedsheets, my legs were trembling. I reached down and turned off the vibrations feeling horny and ashamed.
Wayne stood up, his manhood standing erect and swollen, with my mothers panties wrapped around his hard cock, he stepped up to the head of the bed and his cock was just inches from my face, I knew what he wanted by the look in his eyes, very timidly I leaned forward and kissed it, then again, then I licked it a little, I then let my tongue touch the head that had a drop of precum on it and tasted cum for the very first time.
That was it, with the dildo still deep in my asshole and my cock growing hard again I took him into my mouth, the silky soft skin and salty taste of his cock put me over the edge, I swirled my tongue around the head, tongued his balls and tried to get as much of his erection into my mouth as I could. I could feel his hips slightly pumping pushing his cock deeper into my throat.
I reached under myself and turned the vibrations back on again. My young cock was now swollen again and Wayne noticing this grabbed it and started to pump it with his hand again, this only made me harder and I started riding that toy even harder, his hand grabbed the back of my head and ever so slowly pushed is entire girth down my throat, I gagged, my eyes were watering, he didn’t seemed to care, he slowly increased the pace until he was fucking my face with a handful of my hair in his hand.
Wayne then asked me to stand up, I did and felt the dildo slide out of my asshole with a little popping sound, he then spun me around and pushed me onto the bed facing him, this was turning into a dream day all of a sudden, I was enjoying being a toy for his pleasure.
Wayne lifted up my legs and let his cock settle against mine and kissed me deeply, his tongue in my mouth got me so turned on I started grinding against him, he reached down and squirted some oil onto his cock, I didn’t know if I was ready for a real cock but Wayne never asked, he put the head of his warm cock against my virgin asshole and let it slide in, loosened up but the dildo he entered my ass easily, he began to slowly slide deeper, then deeper, then pulled all the way out asking me “do you like this”, I replied yes and he thrust into me balls deep, over and over again.
My cock was ready to burst and Wayne now had my ankles almost behind my head hammering his cock deep into me, I could feel my cock ready to explode again and told I Wayne this, he reached down grabbed my erection and started to jerk me, that was it, I whimpered I was going to cum and he stroked me faster, I came again, this time there was even more cum shooting out of my cock, I could feel my ass gripping his cock even tighter and then with a loud grunt Wayne began to shoot his cum into my asshole, his strokes became long and deep and we collapsed into an oily sticky mess on my bed.
After a few moments Wayne slowly pulled his half hard cock out of my asshole, I leaned over and sucked the remaining cum out of his throbbing cock tasting my ass as I did it, he then told me that was the hottest fuck he has ever had in his life!
Wayne never did tell my mother about what he caught me doing that day, but we did relive that scene a few times after that, him and my mom broke up about 2 yrs later and I never saw him again, I will never forget him. JJ

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