This story really happened but am not using the real names.
My friend came over one night. His long term girlfriend had broken up with him and he just wanted to hang out, drink some beer, and drown his sorrow.
During the night, he said, "you always seem to have a girl and girlfriends. Any chance one would be right for me "? I said i would ask around, just before he left.
Well, most of the girls i knew were either in relationships or not really ready to be in a relationship. Most of them were friends, but not romantic friends. In fact, most of them were friends with me because i was not trying to "pick them up". One of my closest friends used to come over and use me as her "play doll"; she would put make up on me, practice painting my nails and do my halter like a girl. She wanted to be a beautician someday and i was her "practice toy". She had always said she could make me passable as a girl but i never took her seriously. The idea started.
The next day i talked to her and asked if she wanted to "practice" some more. We made a "date" for that night. She has a boyfriend so she said she could stop by around 5 before she went to her boyfriends place. My friend wanted to come by to drink some more and joking asked if I had found any "prospects".
I had the day off, Friday, for a longer weekend. I bought a pair of thong panties, bra, and thigh high nylons. Then i had to go to an adult store where i found bra inserts, high heels, long flowing wig, and sexy dress.
My "girlfriend" showed up. By this time, i has showered and cleaned myself and was wearing sweatpants and a t shirt in case she made any mistakes it would not ruin good clothes.
She jokingly said, "you don't have to go to work tomorrow so I'm going to make you look like a slutty girl going to a bar to be picked up ". I just replied, "do whatever you want".
After about an hour, she had me open my eyes. The transformation was incredible. My skin looked smooth and even colored ( I always have shaved my face but there was not even a hint of stubble or shadow). My lips were shiny red with a tiny outline of pink. My eyes did not even look like mine anymore. My eyelashes were long and curled up, and she had outlined my eyelids with black pencil and used a smoky brownish gold eyeshadow. She used strokes to draw lines away from the corners of my eyes slightly curling up. I asked her what she did to my eyebrows and she had used some kind of cover up tape and then penciled in thinly arched eyelids. She said once i showered the tape would come off and my regular eyebrows would be back. Of course i knew i would need a lot of make up remover to get all of this off. She had soaked my hands and feet and painted my nails. The skin felt really soft (if only she knew what i did to get ready under my sweat pants). She loves seeing my shock and approval when she is done and she definitely got that. I just started at the mirror. I could not believe it was me. I was so happy but did not hug her as i didn't want to mess up her job. She left to her boyfriends house and I finished.
Under my sweat pants I had used Nair and washed all the hair off my legs, lower back, ass, stomach and chest. I shaved my arm pits and shaved my crotch into a "V" above my cock, which was hard my entire shower and made it easy to shave.
So, make-up on, i out my thigh high nylons on. "Wow these feel good on smooth legs and feet. No wonder women like wearing these", I thought to myself. Then the thong underwear. As i pulled them up, I spread my legs and felt the silk material slide up the crevice of my cheeks. It felt very sexy and I started feeling feminine. Wow, I might need to turn on the AC, i was getting flushed. Then the bra and some glue on the backs of the inserts. Once in place i left them until the glue dried and the inserts did not move around. They felt like they were part of my real chest and i was happy i used Nair so there was no hair to pull.
As i pulled the dress up, i had to move and sway my ass and wiggle to get it over my hips. That did it. It felt so sexy and i felt like a girl doing the same thing. It was an indescribable feeling. Once the dress was on, i put my high heels on. Sliding them on my feet, open toe but with straps up my calves that looked like Roman soldiers wore. I've always worked to make my legs stay toned and the heels really accented my calves and thigh muscles. I felt like a woman..... almost.
I took out the Auburn wig. Long and flowing, went way past my shoulders but framed my face. When i finished brushing it smooth, i decided it was time. I looked in the mirror.
Well, it was me. Not really but it was me. This was like an "out of body experience". I was looking at someone i didn't recognize but i was looking at myself in the mirror. It was a beautiful woman but it was my me. I was not being conceited but i felt like i would want to ask me out, but i was looking at myself. I looked and felt so feminine. Yes, this could work. This could cheer my friend up and he would never have to know. I'm just a friend who stopped by and thought he could use some company; a woman's perspective.
I was comfortable walking in my heels after practicing but when i heard the doorbell, i almost fell my legs were shaking so badly. When i opened the door, I'm so glad he spoke first as my voice suddenly forgot how to form words. It was good too as i quickly realized i needed to speak softer and quieter or he might recognize me.
"Holy shit! Oh, sorry, I was surprised. Um, I didn't know Jeff had company. Is he here?" I opened the door wider to let him in saying, "No, he got called in to work but had me stay so you can still hang out.....unless you wanted to leave?", i said but smiled and slightly tilted my head. "No, no. I was just surprised. I can stay. Thank you."
So, he sat on the couch and i got a couple if beers. When i sat on the couch with him, i could tell he was turned on but also nervous. I know he could smell the gentle perfume and when I crossed my legs, right leg behind my left, my dress lifted slightly showing more of my nylon covered leg.
Some people might think this was cruel, but i had been friends with Mike for so long, i knew him well enough to play this little "cat and mouse" game. A chance to bring his confidence back after a break-up. I could tell he was nervous based on how quickly he finished his first beer.
"I hope you don't mind, but Jeff told me you just had a break up. Did you want to talk about that? Get a girl's perspective?" This seemed to open him up and he told me things even he had not told me, of course he thought i was a stranger that he could open to. After about 20 minutes, he said, "I'm sorry i don't even know your name and I'm telling you all this personal crap. Sorry".
"Vanessa. And you don't need to apologize ". Now, i knew, as his friend, he always joked that Vanessa is a hot name for a girl so i could see his mouth slightly word "shit" when i said my name. I was really getting into my role and tried my best to be sexy walking to the kitchen for beer. He was like a mouse paralyzed by a cobra; every move i made was watched by him.
The evening continued as did the drinks. I could tell he was really relaxing. So was i and I could tell he was really turned on. I have to admit, so was i. Being dressed like a woman, smelling my own perfume and knowing i was turning my friend on was getting me all flushed and turned on too. The beer was really relaxing me and I was started to lie back on the couch as we talked. I didn't notice how close he was. My vision was a little impaired and i did not focus on what he was saying, but i kept smiling and nodding. After one such nod, i felt Mike gently touch my face and then kissed me.
I thought to myself, "shit, how am i going to explain my way out of this", but at the same time i was feeling emotions towards him. After all, he has expressed all kinds of things i never knew and it was, Kind of, my fault. Actually, it was completely my fault. I was playing a female and did not think it was going to Work so well. All of these thoughts were going through my head when i felt his hands around my waist as he pulled me against him and started kissing my neck. Ok, guy or girl, my neck is a huge erogenous zone and i heard myself moan audibly. "Damn it", I thought to myself, "I didn't think this entirely through". As I was thinking this, i felt his hands running the side of my dress, feeling my breasts. I knew i needed to get control of this situation before it got out of hand, literally and figuratively.
Well, that did not work. He pulled me to my feet and then picked me up and carried me into my bedroom. "Oh shit", I thought as he put me on top of my comforter. "Ok, delay him", i thought. So i said out loud, "Honey it's ok, let me take care of this". I thought maybe i would get out of this with giving him a hand Job. That was the wrong idea.
I unsnapped his jeans and started to pull them down. He was straddling my waist so it was a bit of a chore. As soon as he has his pants and underwear off, he slid up my body and before i knew it, my arms were pinned back by his legs. I was not going to be able to use my hands. As i thought of what to say, i felt his cock rubbing on the outside of my lips. He smelled and tasted good.
Now I had fooled around a f couple of times in college (roommate and I gave each other a blow job one drunken night(s)). So, i got myself into this and figured i could relieve him and he would not know any different. I opened my mouth and he slid right in.
As he rocked back and forth, I was impressed at his size. He was about 7" (it's interesting how do many stories are of gigantic 10-12" cocks, wonder if there real or made up). He was about 7", did not get a tape measure out and my mouth was definitely stretched to accommodate him. But he tasted clean and he had this masculine smell to him that was erotic. Maybe that is the pheromone sense but it made me really get into a mode to suck him until he came. Or so i thought. He was moaning how good i felt and said he was sorry for being a little aggressive but it has been such a long time and i was so "hot looking you were driving me crazy all night ". I started to get more into the blow Job with all of his comments making me hot; swirling my tongue, changing the pressure of my lips, etc. Not being able to move my arms made it a little more Erotic and exciting too.
I thought he was intending on coming In my mouth and finishing that way. I was squirming under his weight on me and getting turned on thinking that my friend thinks i am some hot girl and i am about to give him the gift of sucking and swallowing his load.
But, he pulled his cock from the mouth and i felt him sliding down my body fumbling with my dress, lifting it off me. Fortunately my legs were shaved smooth and the thong was pulled tight enough to hide my cock between my legs. But my mind was racing trying to figure a way out of this And at the same time I was getting increasingly turned on feeling his cock and rubbing against my silk thong. To make sure he did not fill my mulch, I told him I was on my period and I rolled over onto my stomach. However I did not realize this gave him the impression that I was open to do more. I felt my song being pulled to the side and his saliva cover cock sliding up and down the crack of my ass. Before I could say anything, And I was increasingly turned on, so I am not sure if I would have said anything, I felt the head of his cock injuring me. It was soft and hard, but smooth and warm,
My friends cock was bigger than I could have imagined it might have been but was thick enough that I felt every rich and vain sliding against my insides. I felt his weight on my back and his warm breath on my neck as he took me. I'm not sure how long I laid there letting my friend get pleasure I fucking me, But as you continue they started to only feel pleasure in what he was doing to me and only made noises of pleasure and even reached back and rubbed His hips as they moved back-and-forth sliding deep inside of me.
After what seemed like a long time, he pulled out of me, only to turn me over an enter me again. As he started sliding in and out of me again, my hard cock became noticeable. I started to try to explain, but he simply said "i knew and Im going to come inside you and carry my cum from that point on." With that I felt his hard cock get harder, actually felt him get a little thicker, and I felt each pulse of come as he shot inside of me. At this time, I had my legs wrapped around his back in my arms wrapped around his neck. It's hard to describe the feeling of his heart pounding from his chest to mind feeling the sweat on his chest sliding our bodies together, and feeling his hot breath on my neck as he recovered.
He laid next to me for about 10 minutes, lightly touching my breasts lightly rubbing his hands up and down my smooth legs as I felt trickles of his cum sliding down the crack of my ass to my back and onto my comforter. Finally, he said he should get going and gather his thoughts from the best sex he has ever experienced and the hardest orgasm he has ever felt. I happily got up and showed him out enjoying the feeling of nylons on my legs and the feeling of his come running down my legs. It was indescribable how it felt when he shot inside me.
Two days later there was a knock at the door and when I opened it he simply said, "no beer this time I just want to be inside you again but completely sober". 20 minutes later, I had my nylons my bra my high heels on, laying on my back, And my friend deep inside me. He came inside me all night and left with a smile an empty balls the next morning.
He did eventually find a girlfriend, they got married, but I was happy to be there for my friend in need.
Vanessa CD, have not repeated this sadly enough.