Ashley becomes the girl of her dreams
Hi all!
My name is Ashley, and I just have to tell you what happened to me Halloween weekend! It was one of the most wonderful experiences of my life! Let me give you a little background on myself. I am thirty-two years old cross dresser. I have been a cross dresser since I was eight years old. I am six foot tall and I have long brown hair that I keep in a pony tail.
All cross dresser love Halloween, it should be known as the cross dressers holiday! Halloween is the only time of the year that every cross dresser ventures out of the house cross dressed. I had been invited to a party where I did not know anyone?. So I needed to find the perfect costume I wanted to make the best of it. I picked Little Red Riding Hood? but with a shorter skirt and fish net hose?. Kind of a Little Red Riding Slut?
The night of the party finally came and I did my best to look hot and sexy and have fun? best type of party is where you don?t know anyone?. Well I was having a good time when this guy dressed like Hercules (perfect outfit for him, wow was he built, come to find out later that he was well built everywhere) came up to me and said wow you?re the hottest girl here you must dance with me! I was totally flattered never had a guy ask me to dance?. I said thank you but no see I don?t slow dance with anyone other than my sweetie?.
He came back again and said listen I told myself I was going to dance with the prettiest girl here tonight well you my dear are her!!! I blushed ? and told him thank you?. Come back when the music is not so slow?.
A few minutes later he came back and said okay the music in not slow and you?re a girl of your word aren?t you? So I said yes of course, I thought why not one dance and he will leave me alone?.
No sooner had we got on the dance floor when I realized that they change the music to slow songs and he pulled me close. He circled my waist with his arms and the moved his hands down on to my butt as he pulled me closer. I tried to break free but he held me tight and said you can?t leave yet we have not had a dance yet. Holding me so close all I could do was wrapping the arms around his neck and lay my head on his shoulder. All of the sudden I could feel that he was obviously aroused. Suddenly I had a nervous moment, A little homophobic voice in the back of my mind telling me to run. This was the moment of truth. I could turn and run and quite possibly regret it the rest of my life, or go with it. I knew if I stayed that before the night was done this man?s cock would be in my mouth and quite possibly other parts of me, I would be his girl for the night.
With these thoughts I could feel my own cock start to stiffen painfully in its tucked back position beneath my cute Red Riding Hood skirt. I placed my hands nervously on his chest and marveled at the feel of firm hard muscle so different from any girl or for that matter anyone that I had ever held in this manner. Slowly he moved his hands down until he had both of his hands gripping my butt cheeks and pulled me closer. I could feel his now totally aroused cock that was seriously pushing against me , I have to admit it was exciting and scary at the same time as he began to rub his now very aroused cock against me!. I raised my head to say I think I should be?. Before I could get the words out of my mouth he kissed me!!! OMG it was a good thing he was holding me tight because my knees buckled and I would have fallen on the floor if he had not been holding me so tight!! Needless to say I didn?t resist, I became putty in this man strong arms with his hot lips on mine!
After long hot tender kisses the music changed. Hercules took my hand and led me to a quieter section of the club house. I just followed along like a good little girl. For some reason my eyes drifted down and I noticed a large bulge tenting out in front of him and giggled to myself as he made no attempts to try and hide it. I did not know whether to be scared or flattered. All cross dressers have fantasized at least once of having sex with a man while dressed as a girl and here was this extremely attractive very well built man who was quite obviously turned on by me and showed no signs of running away. I felt like such a girl knowing that I could turn a man on like that!! What a great feeling!!
After us two glasses of wine he came over and sat next to me on the vacant sofa I had found. I placed my hand on his shoulder as we kissed once more; he moved my hand from his shoulder and placed in on his still erect cock. I could not believe I was dressed as a hot slutty Red Riding Hood in a public kissing a guy and massaging his cock. I was painfully turned on. If I had not tucked my cock back it would have been tenting my panties out along with my skirt. I broke the kiss leaving my hand still resting on his crotch, I was mesmerized by it.
When he told me that every year he rents a room for the night with a balcony and an excellent view of the city, how would you like to go check it out?" Smiling nervously I said," I would love to." We walked out the door, as soon as we got out side Hercules stopped and pulled me back against him. I could feel his wonderfully hard cock pressing against my ass?. What a great feeling that was. I was getting more turned on all the time! He placed wrapped his arms around my hips leaning forward he nibbled my ear and said," Oh baby, you don't know how turned on I Am." He kissed my neck and ground his incredibly large hard cock against my butt. I turned around and kissed him fiercely stuffing my tongue down his throat. Breaking the kiss I said," If you don't get me to your room soon I am going to rape you right here on the sidewalk."
Finally we arrived at Kevin's room. It was very nice a lot larger than I thought it would be. One big room with a kitchen area, a king sized bed and a bathroom with a hot tub sized bathtub. Kevin went to the kitchen and made us some drinks. I sat on the edge of the bed. Kevin walked over and placed the drinks on the nightstand as I stood up and reached down to caress him with both hands as he kissed me. Breaking the kiss we sat down on the bed and continued kissing, with my hand on his thigh and sliding up under his tunic? I reached up and gripped the first cock other than my own with my hand. It was a lot bigger than mine by at least an two inches and much wider I gently massaged it through his underwear my thumb found the pre cum wet spot right at the head? my thumb was caressing the tip with the wet spot it seemed to get bigger and harder omg!!! As I continued to caress it Hercules began to moan softly. It was totally different than stroking my own is was so exciting and very thrilling.
Not sure if the girl in me kicked in or what but the next thing I knew I slipped to my knees in from of him and gripped his underwear and slid them down!! Then gently kissed my way up his thighs until I reached his cock where I leaned forward kiss and lick he tip!!! Then licked my way down the shaft to the base then up the other side before i slid just the tip into my mouth! Hercules did a sharp intake of breath as I felt a tremor down his cock, as it grew even bigger. I started sucking taking in just the head then taking in a little more with each down stroke!! OMG here I was on my knees with a cock in my mouth and it felt so good and so right!!! I knew this may be my first cock ever but there was no way this was going to be my last?. Omg I loved how it felt in my mouth and how it reacted to my tongue and lips!! Yum I only wished I had never waited so long to do this!!!!
I started fondling his balls; I finally looked up into his eyes as I sucked the top half of his mammoth cock into my mouth. As inexperienced as I was I could tell I was doing well by the look on his face and his reactions. I was so into it sucking his cock a bomb could of went off and I would not of noticed! I loved the hard yet soft feel of it. Using my tongue on the silky underside and stroking the part that I could not get into my mouth I soon had minor little tremors running threw him. I reached down and started to caress his balls once again while I applied massive suction to just the head while I furiously licked the slit and stroked the shaft. I felt his whole body stiffen while his cock grew a little bigger. I felt his balls tighten and quiver. As he said," O god here I cum. Until now I had not thought about what I would do when he came?.He held my head, like he was afraid I was going to quit or something!! Silly boy a team of wild horse could not of pulled me off that cock! I felt the first spurt race into the waiting suction of my mouth. I was surprised by the amount. He must have pumped a gallon down my throat. I swallowed every yummy drop.
I held his cock in my mouth until it went totally soft then I finally let it out of my mouth and he fell back on the couch as if he were boneless. I crawled up beside him as he said," That was incredible, I have never felt anything like that ever. Did the earth move?" Are you sure you never sucked a cock before??? I told him, I have never even considered having sex with another guy before but I was more turned on while I was sucking your cock tonight than I have ever been in my life. I watched, as his cock seemed to grow while I was telling him this.
Moved down and over until I had his cock in my hand and moving it up and down brushing it against my lips and check licking the tip each time it came in range. I looked up to see his passion raging in his eyes. Moving down I licked his entire cock never taking my eyes from his then I moved down and completely bathed his balls slowly sucking each one into my mouth and tickling it with my tongue. Panting he said," If you keep that Up, Red or not you are going to get what's coming to you." So I sucked almost the entire cock into my mouth ?..
He Stood up and his tunic off as I marveled at his awesomely muscled body. I could not wait to run my hands over that rock hard body. He returned to the bed he literally picked me up and flipped me over on my back. Smiling he grabbed a tub of KY he had on the nightstand and lubed his cock. I lay there looking at him like ditz blonde wondering what he was doing when he reached down slid my panties down and pulled my legs up onto his shoulders spreading me wide. It suddenly dawned on me what was happening as the tip of his cock came to rest against my tightly clenched sphincter. Smiling at me he pushed forward until I could feel intense pain. I was about to cry out when much to my surprise he backed off and said," You really are a virgin aren't you." Reaching down he took a finger that might be the size of a lot of men's cocks and pressed it into my now lubed hole.
Hercules looked at me with sympathy in his eyes and said," If you don't want me to I won't." Threw the lump in my throat I managed to say," I want you in me." No sooner was it out of my mouth than it was in my butt. I could feel him penetrating deep into my body with every powerful stroke I could see and feel the pressure building within him as his rhythm increased to a near fever pitch. Sweat started to form on his sculptured muscles as they glistened in the light. I tried to move to meet his trusts but he had me hopelessly pined. Never had I felt such sexual tension as I did lying there while this Hercules drove his manhood in and out of me? omg if this is what it?s like to be a girl then sign me up!!!
I felt his whole body stiffen as he rammed his cock deep inside of me one last time. I could actually feel his cock grow a as he began pumping his cum deep into me. The warm feeling of each spurt was something I will never forget. At this moment untouched I reached my own climax and shot spurt after spurt up onto his stomach. This moment of shared ecstasy seemed to linger for hours. Each of us afraid to move didn?t want to ruin the moment. Finally he stopped spurting and after a few moments I could actually feel him start to shrink inside of me, Hercules pulled out of me and dropped on top of me rolling to the side. A feeling of contentment seemed to wash over me. I smiled dreamily and said," I have never felt better." That was the most incredible Experience I ever had of any kind, I have never felt anything that intense ever. I have never been so fulfilled in my life." I leaned forward and kissed him. Thanking him for bringing the girl out in me!
There was no doubt that I liked sex with another guy while playing a girl. I knew it was only a matter of time before I sucked another cock and hope to take another deep inside me?.
Let me know if you like my story?. ashleysagirl@live.com