First a little history about Ashley. She started when I was about 13-14. Going through puberty I found my mothers lingerie and fell in love with the way it felt on me. Since then I have been dressing more and more to the point where I am going out in public. Passing quite well might I add, and getting ready for the transition from Male to Female (Already on hormones). Ashley is 5'5"-5'6", Dark Brown to Blackish hair to her shoulders, Size 4 jeans (Yes a tight little ass), and a firm B Cup almost a C... Handfulls none the less. Now to what happened.
I was at my so called "Job" working like every other day. A suit, tie, although the boss wasn't to keen on my pony tail ;-). I was able to hide my breasts with the ol ace bandage trick, even though some co workers gave me a wierd look. The hours dragged on and on, I thought 5pm would never come. 5 eventually came and I picked up my coat and headed out the door. I had a date tonight, on the town with ashley. When I got home I checked the mail, credit card bills and a Wally world ad. I threw them on the front table and went into my bedroom. I checked the spare bedroom to make sure it was clean, and "Ashley" looking.
While taking off my suit, I prepared a bubble bath for Ashley. Jasmine was the scent tonight. I needed to shave badly, going 3 days without shaving was driving me nuts. After about 5 minutes I slipped into the steamy hot water and took a big breath. It felt good, the warm water covering every body part I had. Ashley was here now, shaving and relaxing in her bath. Another half an hour passed as I slowly washed and caressed my body. Making sure not to miss a single hair, also taking the time not to cut and nick myself to death.
Finally I dryed off, powered my body, and wrapped a towel around me to keep any window peekers from seeing too much. I had my outfit all layed out, a size 4 hip hugger pair of jeans, a very low cut black V neck shirt, and a matching push up bra and g string set. To complete the look a set of 2 inch Black boots. I put clear fingernail polish on, and also on my toes. I but a deep red lipstick on, just the color that says "take me".
I went to a couple local city bars just to lighten the mood. The three places I went weren't very busy so I decided to head to a big city dance club. Getting to the club I could tell it was packed, which was perfect for what I wanted. Alot of music, alot of dancing, and all around more fun. I was there probably about two hours when I went to the bar. Water was my choice since I was driving. And it was pretty hot inside, while I was taking a drink of water he walked up to me... "Hi" he said. I turned to the cutest guy I have seen in a while. He was tall about 6'4" or 6'5", dark hair, and the greenest eyes you have ever seen.
I made him laugh when I tried to speak with a mouth full of water. Spitting out most of it, I swallowed what I could and said "Hi" back. I was mostly embarrassed and turned a deep shade of red. "Having fun?" he asked "yeah" I said "just taking a break for some water". "By the way my names Bryan" he remarked sticking his hand out for me to shake it. "Ashley" I replied back he really had a firm grip. We talked for what seemed like forever, just mainly chit chat and conversation.
I found out he is the assistant manager for the local fitness gym. I didn't notice untill then but yes he was built. Very finely I might add. A yawn from my mouth signaled it was time to head home. Before I even thought about saying something he said "Can I walk you to your car"? I looked him over shortly before I said "Yes". As I made sure to wiggle my butt for him as I walked in front of him and out the door. When we got to my car he asked "So what are you doing after you get home"? I thought shortly before answering "probably relax watch a little tv and goto bed". He looked down at the ground and said in a bashful voice "Would uhhhh.... Would you like some company"?. Only meeting the guy once I probably shouldn't have, especailly with the secret I have. But I said "sure".
He followed me to my house. It was decent for a "woman", single story, one car garage. He followed me to the front door but I stopped him. "Bryan" I said "theres something you should know". He had a puzzled look on his face, probably thinking I was married or something along those lines. "I'm not a normal girl" I said hoping he wouldn't run away, "I'm a T-Girl, I am making the switch from Man to woman". He looked down at the ground again, I was hoping he wasn't mad. He looked out at the street before saying "So??... Your still a woman in my eyes" and with that he gave me the deepest kiss I have ever recieved. Pulling away he had a wonderful smile on his face, which eased my tension.
We went inside, he couldn't keep his eyes off me now. Sitting down on the couch he sat beside me, further away from the TV. So when I turned on the TV he softly grabbed my shoulders and pulled me back towards him. After about fifteen minutes or so went by before he made the first move. He softly put his hands on my shoulders and started rubbing them, oh it felt soooo good. To have a mans hands massaging my aches and pains away. I was a little nervous asking but I thought my chances were good. "Bryan? do you mind if I get more comfortable for you to massage me? I looked back into his eyes and he shook his head no. With that I got up, grabbed his hand, and led him into Ashleys room.
I started by lighting some candles, mostly jasmine but some were unscented. After lighting the candles I turned off the lights. As I walked over to the bed, Bryan was watching me the whole time. When I got to the side of the bed, I took my shirt off making sure he got a good look at my breasts. I then laid down and unhooked my bra so he could have full access to my back. Bryan then asked "Could you take your pants off? I could massage your whole body that way". I am sure he meant it another way, but I wasn't caring at that point. I was too relaxed being Ashley.
I raised my hips up in the air as Bryan slid my jeans off. Peeled them off is more like it, but he had no trouble. He then took my socks off. Massaging my feet and making sure I was in complete heaven. Bryan took his time, massaging every little muscle, every body part. As he was moving up my body from toe to head he got a little friendly with my butt. Truthfully I didn't care, but the good girl in me told him to stop playing around.
Moving to my lower back he straddled me. Putting his legs on both sides of me sent chills up my spine and gave me goose bumps all over. I couldn't believe it, Ashley had a real man on top of her taking care of her like a real woman. He slowly worked my lower back. As he moved to my shoulder blades he moved my bra straps off my shoulders and down my arms. His hands were firm yet gentle. After my arms he moved to my neck, which felt better than everything else.
As he was massaging my neck I felt him leaning down. I couldn't figure out what he was doing untill... *GASP*. He was kissing my back while rubbing my neck, oh that just sent electricity through me. Finishing my neck he gave me a kiss on my cheek and laid down beside me. I turned my head to look at him, still fully clothed he laid there just smiling. I wasn't sure what to do next, I just laid there and stared at him.
He leaned over to say something, but I interupted his words with a very deep loving kiss. Suddenly I thought I had made the wrong move, he wasn't kissing me back. I started to panic thinking "what have I done", but then he kissed me back and not only kissed me but french kissed me. Oh his tongue drove me wild, I forced back into him as we started to tumble on the sheets. I made a move and took his shirt off, all while holding our deep kiss. Oh his body was rock hard, abs of hard man flesh.
Since I was just down to my g-string I decided to even the odds a little bit. I threw him on his back and started undoing the button and zipper to his jeans. His relaxed fit wranglers slid off his legs, revealing a set of M&M boxers. At least his chocolate will melt in my mouth and not in my hand. After giggling for a second I started to peel his boxers off, slowly but surely they revealed 7" of thick manhood. I gazed in amazement for a split second before I caught myself.
I started stroking it, thick and long it was. I wanted it all, oraly, analy, I didn't care I just wanted it. I started licking his head with my tongue. First just one or two licks teasing him with every touch. Then I circled his head letting him feel my warm juices from my mouth. I took his head into my mouth after that. Just his head for a while, getting used to it. The more I bobbed up and down the fruther I was able to take him. First 3 inches, then 5, almost 6, but what I was doing was driving him mad. Finally he couldn't take it anymore, he grabbed my head and shocked me. He forced it all the way in my mouth and down my throat. He was going in and out of my throat, as fast as he could untill he held himself against me. Grunting and shuttering he orgasmed, all down the back of my throat. He came, he came all in my throat
As he started to pull out I made sure he was clean, I licked his head and stroked it a few times cleaning out the chamber. After I finished cleaning I layed back on the bed, still horney and ready to go. I still had the salty cum taste in my mouth when he came over too me. He kissed me once and said "turn on your stomach". My body wiggled with energy, I wasn't sure what he was going to do... or try to do. He first layed on me, putting his still fat dick inbetween my butt cheeks. Oh it felt so good to have a man behind me like that.
He started to kiss me on the neck again, then he proceeded down between my shoulder blades, then down to my lower back... by this time I knew. He kissed both my butt cheeks and then proceeded to take my g-string off with his teeth. After sliding it off my feet, he proceeded back up to my butt where he would make himself known. He took a deep breath and sent a cool breeze of air around my hole. It made me pucker and tighten up, but I am sure thats what he wanted.
He told me to raise my butt, so I did as told. He came up rather quickly grabbing my thighs and forcing himself near me. His warm tongue clipping the outside of my hole. I couldn't believe that this was happeing, My first tme with a real man and this was going to be my cherry popping too. My first time with a man, My virgin hole about to be violated. Now hes fluttering his tongue at my hole. I am so wet right now and he is only making me more wet. After teasing me for what seemed like an hour, he pushed his tongue into me making me feel his warmth inside.
With his tongue now inside me I am panting away, feeling every lick, flutter, and move of his tongue. Whether it was out of lust or love I finally said it... "Bryan... Bryan... put it in me". I wanted it so bad, so bad i could taste it again inside my mouth. "Ok Ashley get on your stomach" Bryan panted. Bryan then asked "Do you have any lube?". "Yes" I said "Its in the top of my dresser". It was KY my favorite and personally it felt better than any others.
Bryan got the lube and put it on himself. He layed himself on top of me trying to get a easy angle. When he got to my hole I said "Bryan?", "Yes" he replied, "Do me, do me like a REAL woman" I begged. Bryan needed no more, he put his head up to my hole and pushed gently. As wet as I was, it was still alot of work for him to slide in. Bryan was pushing in while I was trying to wiggle my hips to help, I must have gotten a good position because he slid in deep. More than what I wanted for the first time.
It hurt some but also felt good. Bryan pulled out till just his head was in, and started to re work it. In and out, In and out, slowly he pleasured my little hole. Before too much longer we were banging away, He was pounding me harder than ever and I was loving every minute of it. I started to scream, it felt so good that I just wanted to yell out. In the middle of everything I started to feel something in my gut. Yes part of it was his member, but it was something else, something bigger. "Bryan" I yelled, "yes" he panted back, "I'm feeling strange inside, like funny strange" He seemed to slow his pace a little when I said this. The feeling went away when he slowed down so I said "Forget it, just go faster". With that Bryan took off in a flurry of pumps, each one faster than the last. My funny feeling came back, only this time I didn't let Bryan know... I raised my butt up in the air to really feel him inside me. Still pounding away at me, Harder and harder.
Finally the feeling came rushing back, when it did I got up on all fours. Bryan was screwing me like his bitch in heat. Bryan kept his pace as I screamed "More MORE MORRE!!!". I couldn't keep the feeling in any longer, I couldn't hold it back. "OH GOD BRYAN" I screamed "CUM INSIDE ME PLEASE CUM INSIDE ME!!!". He must have been close because he released a HUGE load inside of me. As his load was releasing my hole clinched, and I jerked back on Bryans cock sending him even deeper into me. I started to jerk and spazam. My body releasing from my first ever orgasm like that. He held me up until I was done with my orgasm, then we fell together. Laying beside each other, his arms around me.
I fell asleep right after that, I woke up the next morning to a empty bed. But a note was on the pillow it simply said "To the woman of my dreams" it also had his phone number on there. I called it the next weekend, and I am sure you can imagine what happened.