That was this summer. I had very long relationship and last year i got ridden of it. So I sex occasionally wit various girls till then. One night this September I was very very tired of everything. Job went finally better and some private investing also, but I had being working for 14 hours a day at time. It was About 1 am in the morning and was just went of from long shower and about to lay down on my bad.The voice from the other side of cell phone was very pleasant, some kind of baby talking voice. Voice said" Annnn' what what do want from me now?...LOL.. i said "who is this?&... Continue»
When I was much younger my neighbor, Lana, a divorcee, kept an eye on me while my folks went out of town. It was she whom formally introduced me to cross dressing and it was quite to my surprise. Back then I could actually pass for a woman due to my build. My hair was shoulder length and my body was small framed with feminine features.
I used to try on my mother's panties and clothes even though they were too big for me. Lana, on the other hand, had a great body. She was athletic and did not have a huge chest or big ass. She had great curves and was well defined. When my parents asked if I could stay with her one weekend while they attended a conference I knew I would get my chance to wear her panties. That Friday Lana had gone to the market to pick up diner. I ran to her room and immediately began looking in her drawers. I tried on her garters and stockings, panties, bras, and even a white silk teddy. It was during this time she returned home. I did not here her enter her home, when she walked into her bedroom, there I was in the midst of trying on her panties and bra. She exploded! She commanded me to take them off, remain naked, and stand in the corner of the room. She asked me if I liked dressing like a little girl. I can remember her screaming about how I had no right to go through her private things. She refused to let me cover myself or get dressed. She told me to stand their, still naked, as she screamed and demeaned me. I was very timid, so I did as I was ordered, flinching at the point of tears.
She opened the drawer and threw an assortment of clothing and lingerie at me while screaming at me. She stopped, got quite, looked at me and marched at me. She grabbed me by the wrist and took me into the bathroom. She began running the tub with scolding hot water. She kept screaming over and over, "So, you want to wear women's clothing. Well, let's see how you like being a woman!" I was so terrified. She almost threw me into the tub of hot water and ordered me to put my legs on the edge of the tub and proceeded to shave them, my arms, chest, and cock and any hair in my ass. If I tried to pull away she smacked me hard, leaving a hand print, and warned she would tell my father what she had found me doing. I was in full on tears from the humiliation, pain of the hot water, terror of what was happening, and her anger. She washed me in a bath with fragrant bath oils. She scrubbed my skin with a coarse brush until I was red.
After she had taken what seemed like hours to scrub and humiliate me she dried me off and took me to the bedroom. She proceeded to do my attach fake nails and paint them. She kept a stern face and kept saying, "If you do not do as you are told I will tell your mother, father, and all the neighbors about you playing dress up in my underwear." When my finger and toe nails were dry she had me move to the make up table where she proceed to do my long hair in a bow and give me a full make up. With that finished she spun me around and I could not believe my eyes, she had made me a woman.
My cock was throbbing as she took a scarf and tried to tie it to my leg. She commanded me to do something with it. When I refused a hair brush smacked my leg and tip of my cock with unbelievable f***e. I began to go to the bathroom to get off and she said, "no, sit on my make up bench facing me." She sat in front of me and watched as I got off, with difficulty,and sprayed cum on her carpet. After which she proceeded to have me clean my genitals. She walked to her dresser and threw me a collection of underwear. I sat on the edge of the bench and slid silk stockings on my legs, a pair of crotch less panties, and garter. She then put a matching bra on me and padded it to give me a chest. After she laced me in a corset to make my figure more curvaceous followed by a knee length skirt and lite summer blouse and flats.
While I sat there she began packing two bags. She filled both with women's clothing and accessories one for her and one for me. All the while she continued to scream so you want to be a girl, well here is your chance. By this time I was again on the verge of tears and scared to death of what she was going to do to me.
She ordered me to go to the garage and get in the car. She followed and tossed the bags in the trunk. She then said we were going go away on our own little adventure so we headed to Mobile, Alabama for the weekend. On the way she told me how I was expected to act. I was to be a proper young lady. I would wear only what she picked out for me and do as I was told. Since I was going to violate her privacy I would pay the price. I was scared, humiliated and not about to argue or resist. I then saw the crotch of her jeans were wet. She was turned on? I did not understand at that point. I soon felt my cock, stilled tied to my thigh, start to harden. I learned at that point how much another persons arousal was to me and how much it turned me on. I was no longer terrified I was exited. I was ready to play this game.
When we arrived in Gulfport, she stopped at the gas station. I walked in to get a drink and pay for her gas and I saw myself in the windows reflection. I could not believe it was me. I was a woman. When I was getting my soda a young man a few years older than me approached me and fell all over himself to talk to me. I paid and gathered myself. Before I could reach for the handle he ran over and he was holding the door smiling and talking to me. When I saw Veronica she had a smile ear to ear. She laughed at me and said you liked that attention did you not. I said yes and understood I was attracted to both guys and girls.
Later that night we went to bed. I felt her slide into my bed and when I rolled over she was sitting there naked. She laughed at the expression on my face and leaned in a kissed me deeply. I felt her tongue slip between my lips as her hand dipped under my nightie and into the Hello Kitty panties I was wearing. She took me in her arms and began kissing my neck and working her way down. She stopped and sucked on my nipples, licked them and took them between her teeth and pulled on them, she pulled hard and stretched them out until I cried out,"Oh, God, yes mommy! Please, hurt me more!" It was at that point I heard her let out a guttural growl and she pulled hard and fast. I was in so much pain and yet experiencing so much pleasure. She worked her way down to my cock and began kissng it and gently sucking. All at once I felt her bite into the head and squeeze my balls as if she was cracking walnuts. I screamed for more! She took all seven inches of my, or should I say her, cock down her throat and worked it in and out of her mouth until I came. She looked up at me and crawled to my lips and kissed me. In a moment she blew my load into my own mouth and began passionately kissing me. I swallowed and sucked her mouth looking for more. She then threw her leg over me and lowered herself onto my ready cock. It had not taken long for me to regain full erection and she was ready. It was my first time and I came in an instant. She laughed and said, "By the time this weekend ends you will definitely be able to go longer." She took a bottle of hand cream off the night stand and lowered her self back on my still erect member. She spread the cream all over a dildo she also had in the nightstand drawer and lubed it up. Without a word she leaned back and pushed it deeply into my unknowing ass. The pain was immense. I felt it from the top of my head to my feet. She smiled and said,"Well, you have lost both cherries!" and pushed it even deeper. She began moving up and down as she held it in me. I was cumming again before I knew it. Soon after we fell asl**p.
The next morning I found a cute summer outfit and again she dressed as her daughter. The skirt this time was much shorter with a blue top and sandals. She secured my cock and balls between my ass cheeks. She explained how I would have to walk and bend so as not to give anything away. We shopped and fucked in many dressing rooms that day and no one had a clue.
That night we found out about a festival. At the festival a young man asked me to dance. We danced through several songs and by the end of the evening we were making out on the dance floor. We left the dance floor and walked to a secluded area. He tried to grab me but I deflected his advance as we made out. I was so glad to have my cock secured tightly in place so it would not be noticeable. I remember keeping space between us. When another couple walked past I turned and he pressed against me I could feel his cock in the crack of my ass through my dress. I grabbed the railing and he proceeded to dry hump me right there kissing my neck. I will never forget him cumming. The feel of his pulsing cock in against my bottom and the feel of my dress in my boy pussy. At that moment Lana came out of no where and took my hand and scolded me and him saying, "She did not raise a slut and I was too young for this stuff." The young man turned 10 shades of white when he heard that and bolted when she told him to get lost.
Lana screamed at me the whole way back to the hotel. She then removed my clothes and put on a 9 inch long, thick, strap-on. She yelled if I was going to be a care free slut she was going to show me how it felt. She bent me over and proceeded to slam her dildo in me. It hurt so bad! She had just gotten the tip in me when she realized what she had done, she had forgot to use lube. She began to pull out and I said,"NO!" She slid the large rubber tool into me bit by bit. OH, MY, GOD it hurt so good and she wore my ass out. When she pulled out I heard her let out a gasp. I felt my hole and it was stretched and gapping. She said, "Maybe you need to take it easy." I told her it was okay and I wanted more. She opened the lube and put the tube to my ass and squeezed. I felt it shoot into me, I was that open. She began to fuck me again only this time I was on my back with my legs around her shoulders. She fucked me and jacked me off. I came all over myself. She scooped up my cum and fed it to me while she pumped me harder and deeper. It was sheer heaven. That night I had the best sex I have ever had in my life up to now. That summer I learned everything about being a girl and for the next several years I made love to a beautiful woman dressed as her daughter. She used toys large and small to love and penetrate me on a regular basis.
It was a year and a half into our relationship she introduced me to her friends and a man. One weekend while I was staying with her she and a male friend took me away for the weekend. That weekend I was taught how to please a man and had my first real cock in my ass. That is a story for another time.