From a shy virgin college boy, to makeup and heels

From a shy virgin college boy, to makeup and heelsSo I’d been away at college for about a month, didn’t have many friends, or any confidence to speak of. Not long after starting classes I started dating this older girl, she was cute, but a real bitch, she wouldn’t fuck me, she’d treat me terrible, and make me wear her panties while I ate her pussy, and after she came, she would watch me cum on my stomach, and then run her fingers through it, and stuff them in my mouth. While this would turn me on to a point, I knew this girl had to go, after a few weeks I finally managed to get away from this abusive girl.So a little time goes by after the breakup, and all I can think of is how it felt to wear panties, I got my nerve up, and went out and bought a few pairs, some stockings, some skits, tops, heels and a small bit of makeup. I spent the few nights dressing up, and trying my hand at makeup, I did alright, and I didn’t look bad, as I already had long blond hair, almost no body, or facial hair, long legs, and a nice round ass. After a few days of playing alone, I decided to check out the local alternative lifestyle club, I heard they had drag shows, and it was a fun place, so I caked on the makeup, eye liner, blush, and lipstick, put on my stockings, skirt, padded bra, and a tight cut button down, it was the best I’d ever looked, I didn’t plan to meet anyone, I just wanted to get out there.I arrived at the club via cab, the cab driver kept leering at me in the mirror, I wasn’t into him, but I was flattered, as I know my body was rocking. When I got there, ankara rus escort I sat at the bar, it was an older crowd late 30’s to 50’s I would say, and here I am 18, and nervous as hell, everyone was nice, I even got hit on by a few guys, I mainly just sat there watching the baseball game on tv. Just as I was about to leave I hear a voice say “honey is this your first?” First what I ask? “Dressing up?” as I turn around I see this late 30’s tall red headed goddess, umm sort of I stuttered, “you did good hun, my name is Jessica” We sat and talked for about two hours, she was so nice to me, before I left I ask her what she would charge to help me with makeup, nails etc, she said “Honey, nothing at all, here is my number, call me, and I’ll have you over for a makeover. Over the next two weeks Jessica, and me talked multiple times a day on the phone, she told me how she had been kicked out of her home at sixteen as her parents didn’t accept her transformation, and really we talked about everything, the girls who’d been shitting on me, my classes, nothing really sexual, just becoming friends.After two weeks of talking we set up a day for me to come over for my makeover, I got to her apartment around 4PM on Saturday, she had a cool place, with lot’s of great art, and music. When I got there, she was wearing yoga pants, and a tank, she’d told me she was on hormones, and I noticed how nice, and round her breast were, her ass was amazing too, anyways we went to the bathroom where she told me to strip, I was so nervous, ankara rus escort bayan but I did anyway, she said let’s shave you, I hesitated, as I felt I was pretty smooth already, she insisted, and the two of us went to work, I was a really turned on as she shaved my ass, and lifted my balls to shave them, and my scrotum, she noticed, but didn’t make mention of it, just smiled, and kept going, after that she gave me a mani, and pedi, and painted my toes, and put fake nails on my fingers, she then had me take a shower, she got in with me, and washed herself too, as we were going out after, and time was running out, I tried not to stare at her in the shower, perfect tits, flat stomach, completely shaven long cut cock, I kept my back to her, as I didn’t want her to see my erection. We got out of the shower, we put robes on while Jessica did my hair and makeup, after that, I was ready to get dressed, see through black panties, black stockings, black bra, heels, as Jessica clipped my bra, she turned me around to see my massive erection, and precum soaked panties. She smiled as I stared into her eyes, I’m sorry, for what she said, I’m not sure, I’m embarrassed by my erection, and honestly I;m just used to being sorry, she pulled me close, and hugged me, “honey it’s o.k, you don’t have to be afraid, or nervous. I pulled back tears in my eyes, just then she leaned in and kissed my lips, ever so softly, I quivered I was so nervous, she took me by the hand, and led me to the bed room, where she dropped her rus escort ankara robe, and laid me on the bed, climbed on top of me, and kissed me deep, and soft, while gently scratching me with here nails all over my body, I’d never been so intoxicated by someone in my life, I could feel her growing cock on my stomach as we made out, she kissed her way down to my wet panties, and kissed my cock through them, she then lifted my legs, and licked my ass, I moaned, as she slowly stroked my cock, and licked my hole, she slowly slid my panties off, and started to rub a finger in my tight ass, all while working my cock with her mouth, I whispered I want yours too, she then turned around and slid her cock in my mouth, I sucked, and sucked and she grew, and grew until she was every bit of 9″..I was a natural, relaxed, I didn’t gag, as she slowly fucked my face. After minutes of this awesome 69, she pulled away, and crawled back on top of me, began to kiss me, as she rubbed some lube on my ass, and her cock, and pushed my legs far apart, and back as she started to drive it into my ass, never breaking eye contact, she was so gentle, and caring, it hurt a little bit, but she knew just what to do, she’d push in just right, and put my legs in just the right place to make it feel amazing, it went so slow, and she kept kissing me, and rubbing me all over while fucking me so good, after minutes, I ask if I could get on my knees, she smiled and pulled out most, but not all the way, there I was on all fours being gently fucked my the beautiful shemale with a huge dick, while on my knees I came without even touching my cock, she noticed to as my asshole gripped her perfect cock with every thrust, it was soon after that she came deep inside me, when she did she forced me to lay flat, as she lay on top of me, her hot cum deep in my ass, we lay there kissing until we fell asleep. Best night ever.