- Transgender & Crossdressers
- My Life as a Crossdresser Ch. 01
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Hi,
This is my first ever attempt at writing a story so I would appreciate constructive feed back. Also, this is just mainly set up and background info with only a masturbation scene. Some of the following events are true and did happen to me.
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It has been five months since I turned 18 and thankfully, high school was in my rear view mirror having just graduated with honors. Being as physically small as I was for a guy (5 feet and 110lbs) you can imagine how much fun it was going to school every day. To make matters worse, my facial features were a bit more feminine then they should've been for a normal teenage boy. I also had a lack of any real facial or body hair but it didn't matter anymore, high school was over forever and I was freed from my torment. Plus, this summer had the makings to be something special. You see, I was a closet cross-dresser and very bi-curious, two things I dearly wanted to explore but didn't have the means to do so until now that I was 18.
The first thing I did when I turned 18 five months ago was get a credit card, and since I was a very shy person, the credit card made a huge difference. It allowed me to shop online and buy the women's clothes and shoes that I wanted so badly without having to go into a store and actually interact with people. Through a bit of trial and error I was able to assemble a few different outfits that fit me perfectly and buy a few pair of high heels to go along with them.
And since my summer job allowed for me to be home alone a lot during the day I found myself walking around the house in women's clothing all the time. One day it would be a skirt and a blouse, another day it would be a nice two piece bikini, but regardless of what I was wearing that day, it made me feel great. It was also during this time that I discovered what I thought to be a very embarrassing fact actually had its upside when I was wearing panties, bikini bottom's or more form fitting women's clothes. Since my cock was so small (only 5 inches hard and 1.5inches soft) I had a really easy time "hiding" it. In fact, even when I was wearing something as revealing like a bikini, to anybody who didn't know any better, I would look like nothing more than a very flat chested girl.
About a week into summer and cross-dressing all day, I decided that I wanted to really explore my bi-curiosity. So one night, after getting dressed normally, I left for work early so I could make a stop at sex shop on the way in. As I got into the parking lot, I started to get very nervous, and sat in my car for 10 minutes or so before I had the nerve to move. When I finally made it into the store, there were one or two people in there and the store clerk was busy helping them out, so I made my way to the section of dildos and butt plugs hoping that nobody had really seen me. I was starting to look at the collection of sex toys and decide which one I would by when sudden from over my shoulder I heard
"Hello, is there anything I can help you with?"
Turning around red faced, I saw it was the sales lady and as quickly and calmly as I could I replied, "Hi, I was just....... Just... looking for.... A dildo.... And a maybe... a butt plug."
She replied, "Is who this is for new to anal?"
I couldn't verbally answer, so I just nodded my head. After seeing me nod, she quickly took one butt plug and one dildo and handed them over to me.
She said, "Well these should be a good place to start. Is that all you wanted?"
I replied "Yes" and a few minutes later I was leaving the shop heading off to work with a 7 inch dildo that wasn't very think, a 5inch long butt plug that had a 2 inch diameter at the largest point and a bottle of lube sitting in my car. The whole time at work I couldn't help but think of how turned on I actually was by the whole situation and how I really wanted to get home to try at least the butt plug that night.
And when my shift was finally over, I rushed home with more energy than usual, and went straight to the bathroom, figuring it would be easier to clean up in there if I made a mess. I quickly stripped out of all my clothes and placed the butt plug on the edge of the bath tub. As I was lubing it up, I was a bit surprised to see that I was completely hard and was getting really excited to try this.
After the butt plug was completely lubed, I positioned myself over the butt plug straddling the edge of the tub. Slowly I lowered myself until I felt the tip of the plug at the edge of my hole. I paused for a moment, and continued, moaning softly as I took in the first inch of the plug. Stopping there, I slowly started to ride the plug up and down, taking in more of the toy and getting stretched further and further on every down stroke. I was in heaven; it felt so good riding the toy. I started to leak pre cum when I made it half way down and I didn't even stroke my cock once. I continued to ride the toy, speeding up the pace, fucking myself faster and faster with the plug. All the while I got more and more turned on and my cock got harder and harder. I continued to fuck myself as hard as I could with the toy before suddenly the whole plug was in me except for the flared base. At that moment, when I took the whole plug inside of my ass, I experienced the most intense orgasm in my life. I shot rope after rope of cum all over the tub leaving a sticky mess and when I tried to get up, I had to steady myself because my knees and legs were weak from it. Now I masturbated like any regular teenager, but I have never cum so hard, and never ever have I been able to cum without touching my cock. This was the most intense orgasm of my life at that time.
After my legs regained their strength, I slowly walked across the bath room to get a towel to clean up the mess. After cleaning up the mess, I started a warm shower. Standing underneath the shower head, I reached down in-between my legs to find the base of the plug. Slowly I started to pull it out, enjoying the sensations of it sliding out of my hole slowly. After I came back to my sense, I slowly soaped my body, and washed myself and my toy clean. Still riding the high of the orgasm while I was drying myself, I thought, "If the plug was this good, I can't wait to try my dildo."
At this point I wrapped the towel around my waist and headed back to my room hoping nobody was up and catch me carrying a butt plug in the house. Inside my room, I found a pair of thong panties and put them on, making sure to tuck my cock away properly to complete the perfect silhouette. I was now finally beginning to feel tired, and climbed into bed. I fell asleep thinking that I had to get onto that swingers site I found so that I could further explore my desire to cross-dress and my bi-curiosity. After all if a toy was that good, the real thing must be better right?
To be continued........
- COMMENTS
Anonymousover 2 years agoI guess i started becoming Paula when i was around 13 i had 3 sisters and anytime i was alone at home i would dress in their clothes. I loved wearing girls clothes and i felt girly and slutty. Sometimes id wear a pair of panties going to school under my trousers and the feeling on my winky was so good. One day i was in the toilets and peeing when my friend yanked my trousers down and saw i had a pair of pink hello kitty girl pants on and he had a confused look and asked me why are you wearing girls pants i replied our washing machine is broken and i had nothing else so i took these besides they feel comfortable. He said ok and promised not to tell and i told him he could come over some time to my house and try a pair if he wanted. A few days later he asked me could he come over and try on pantys and i said yes but tomorrow will be the best time as we would have a few hours before anyone else gets home. Next day we headed to mine and i got several pairs and we tried on different ones together. We did this a few times together until one day he asked do you ever wear any other girls clothes i told him sometimes i do dress up completely as a girl and did he want me to for him he said yes so i went and borrowed some things and came back into my room wearing a girls uniform and his eyes widened. I had a white blouse with a training sports bra a grey skirt black knickers white knee socks and black flat shoes on. He had just a pair of lace trim pants on and i could see he was getting an erection. I said do you want me to be a girl for you he said yes and i sat beside him on my bed. We kissed and i reached into his pants and played with his hard cock as his hand went under my skirt and i opened my legs for him. We emded up jerking each other off and both spurted out our cum. Next time he asked me to suck his cock and i did in a sort of 69 position and he played with my cock and balls. He groaned and next thing spurted his juice into my mouth i gagged a little but the taste was ok so i swallowed it. This went on for a while and we did a 69 and were sucking and drinking each others cum every time and oxxasionally he would put a finger into my ass as he sucked which made me cum quicker and felt so good. Next time we were doing it he fingered me then asked could he put his cock inside instead of his finger i said he could try. It hurt so i got a tube of body cream and coated his cock and squeezed some in my bum and we tried again this time less pain and he got it into me. After a little while there was no pain and it felt so good as he fucked in and out of me. After a few minites he said he was near so i wrapped my legs around him and said cum inside which he did. That was my first real sex and it was good. Since that i have had sex with a lot more guys and girls so i have the best of both being bisexual.
Anonymousover 9 years agomy wife came home Friday with a smile on her face she told me to go take a shower and put on my prettiest undies I've got a date for you tonightwith a smile on my face I did what she said about a seven o'clock there was a ring at our doorthere stood a couple the girl I recognized she was one of my wife's girlfriends the guy was very handsome we invited them inside as he came in he kissed me softly on the cheek and patted my bud and told me that I have something for you tonight we sat on the sofa he sat next to me and she sat next to my wife on the loveseat we talk for a little bit then my wife told me to show him what kind of a cocksucker I am with that he and zips pants and slid them down I got on my knees in front of them and I slowly lick his cock from his balls to the tip he got harder and harder finally I slipped his cock and barely in my mouth push down on the far as I can taking all of them I kept it that way for a little bit and then I started going up and down my rhythm getting faster and fasterI could tell that he was really enjoying it and moan once in awhile within about 10 minutes I could feel him starting to tense up I think of them as far as I could my mouth and with that he came he shot his cum down my throat when I felt him stop I slowly slipping back out of my mouth I reach with my hand that vary based by his balls and stroke it up to get the last little bit of cum out of them I turned just so the girls can watch me lick the last little bit on tip of his cock by then they'd already stripped off and enjoying each otherI finally got up and whispered in his ear I can't wait to have you in my pussy we both went off to my bedroom where he didn't even wait for me and dress she just laid me on my back lifted my skirt pull my panties aside and slipped his big cock in me I squeezed in from time to time he love that was a Mon it took him 15 minutes to climax and I loved every bit of it he finally pulled out and the girls are staying here watching the whole show they loved it and asked me if I was the best fuck I ever had and I reassured them it was we went back to the living room he didn't even bother to get dressed we set there for a little bit at a drink the whole time I was playing with his cock it didn't take him long he was hard again we didn't even make it to the bedroom it is sleeping on the floor and gave me another good fucking of my life after a while we all got our breath they got dressed and left as he was going out the door asked if he could come and dating some more before I could even answer my wife's it anytime you want her you can come get her the best day of my life
Anonymousover 9 years agoby the time I finish reading your story I played with my cock so much I shot cum everywhere the thought of putting my cock in your pretty little mouth made me cum now I fantasize about putting your legs up on my shoulders pulling your leg pretty panties aside and putting my big cock in you well your wife sits there and watches I even thought about putting my cock in her pussy hot pussy and when I get ready to come pull out and cum all over your pussy and make you lick it up thank you Danielle
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Anonymousover 9 years agonot only does your wife approve of your dress she seems very happy about it and she is willing to share a cock with you and watch you have sex you and you are very lucky special girl
Anonymousover 9 years agogood night my wife had me put on the panties and brasafter walking around in her looking at me she finally asked me straight out if I had ever had sex with a man I knew this is my time to finally come out I told her yes she told me six months earlier that she would like to have sex with a woman and she's been doing it for 6 months now so what can I just tell her the truth her hands immediately went to her crotch I could see that she was excited over the thought of me doing something like that she asked me straight out have you ever sucked a mans cock I told her yes dear I can see this further excited her I asked her if she would like to watch she immediately said yes I told her if she'd go to the living room and sit there and be patient we would go and she would get her chance to watch she didn't have any ideal that I had closed - in my closet imediately gathered up skirt and blouse build some stockings I grabbed one of her purses and I put a pair of high heels in an some jewelry and makeup and my wig I wanted to living room after I put my clothes over my skirt my blouse I told her let's go we got into a car went to a place that had a glory hole that I need about once we were inside I stick close to the hole and a motion to come to me to help me she didn't understand at first 9 big my pants are falling down she finally got to see me in a skirt and blouse then I told her to bring her purse over to me I put on my shoes my wig my jewelry and I had her help me with the makeup by this time there was a man that got into the next booth to us I stuck my finger up to the hole in motion Tim and he put his big thick cock through it I got down on my knees can I put them in my mouth glanced around behind me and she had already taking off her clothes and was masturbating after few minutes on motion to come to me where she could get a better look and maybe participate she did so in a hurry I pull them out of my mouth and we both licked on him and then she finally put him in her mouth for a little bit after a while she pulled them out and offer them up to my mouth again which I gladly suck bottom she whispered into my ear I think he's about to cum I pulled his cock back out of my mouth and look better and told her sweetie I hope it he does soon after he filled my mouth with cum actor he's finished I squeezed on them and got the last drop in turn sideways so she could watch me lick the last little drop your cum off of me after that I got up and motion film one more time and told him to put his hand through the hole I put his hands up underneath my skirt lemon feel around letting him know that I had women's clothing on this present excited him cuz he reached inside my panties and got my cock I put it to the hole and let him suck me till I came actor that I grab my regular clothes and put them in her bag and she looked at me aren't you going to change I told her no this is the way I'm going to leave I put my sunglasses on open up the door and me and her walked out and as we got to the door and managed to register said you ladies have a good evening we got out to the parking lot and the man came up behind ur still in the room next door and asked if we'd like to go somewhere else my wife and me we're going to the house why don't you follow us he did so and that night we had great sex she wants me to suck his cock couple more times and watched him take me he fuck me hardthe second time I come to the house my wife asked him if he was married he said he was but he thought his wife might be a bit of a prude he showed us a picture of her and Linda instantly jumped on it why don't you bring her over for dinner in about a week hey did they showed up with his wife actress having a few drinks and smoking a little bit my wife offered to show her around the house they disappeared for a while and lo and behold I look in the bedroom and sure enough they were on the bed together my wife is going down on her pussy like it was our first one we all had sex together like this many many times and I enjoyed it this is my story Danielle
Anonymousover 9 years agowhen I was 4 years old I had a playmate named Kate I played with her all time she is the daughter of my mothers best friend me and her spend more time together than me and my two brothers one day Peggy it but Kate a leotard and some tights and she danced around and got me to dance with her and finally talked her mom in saying that I needed Peggy being who she was she finally gave in and the next day she want bought me a light blue pair of leotards and tights and mean Kate played in them all the time we kept this up for several weeksone day Kate asked me if we wanted if I would like to play dress up with her we went into her room she was my best friend I didn't care she brought out server pretty dresses some shirts tops and she gave me a pair of her underwear and told me to take off my clothes and I put them on it didn't seem to bother me none and then we started trying on clothes she put one dress on me after another finally she decided she like the one dress that I had on on the best she gave me a pair of her shoes and socks and we want the front room or peggy was thank you sit there and looked at it for a little bit and said look at my pretty girlsPeggy then told this why don't you girls go out and back in play for the rest of the day that's all we did I stay dressed up and girls clothes and we played finally when we come in she made me change it back out of my clothes so I could go home the next day I returned and Kate couldn't wait to get me dressed up again I stayed like this for a long long time hurt she kept me dressed up as your little sister and finally told me that my name will be Danielle from now on her mother agreed on it and Peggy at one point started getting these little pills and asked me if I really wanted to be a girl I told her I didn't mind and she gave me a pill everyday to takeI took these pills with a question then started buying me clothes and while my mother is at work she dress me up it's pretty as possible and me and Kate would go shopping with her we try on dresses in girls clothes have a good time go to the mall I stay like this for 2 years and we finally moved away from Pennsylvania me throwing a fit NK throwing a fit my mom finally brought me back up to see Kate she is packed for a week at the end of the week me and Kate through such a fit my mom ended up let me stay I stay there for over 2 months piggy cafe dressed as a girl the whole time I enjoyed it I finally started meeting some of Kate's little girl friends and we all play together nobody was any wiser I was just Danielle finally after 2 months my mom comes to get me again we went back home and I had put away my clothes being unhappy my mother at lunch time took me back to Peggy's this is where I stayed for a year you got me and rolled into school so I could go to school and I stayed a girl I was enrolled as Danielle the rest my life one on this way I finally got married one night after having sex I confess to my wife that I'm used to dress as a girl she want the dresser drawer and gave pulled out a pair of panties and told me to put them on I did so she looked at me and saying how cute I was fresh for a lil bit bigger then what they should be that was due to all the pills that I take an and she then pulled out a bra and told me to put it onI put the bra on and she looked at me and we played for a little bit the next morning she got me up and she told me it was time to go shopping I didn't know what it meant but we went to the clothing store and she had me try on dresses and skirts and blouses which she bought for me quite a bit of lingerie when we got home she had me shave my body and from then on she told me that I was going to live as a woman this made me happy me and her still live together we have a great life this is my real story Danielle
Anonymousover 11 years agoYou're on your way to a great life if you continue. There's nothing better feeling than a real cock buried in your ass, especially when the guy shoots his hot load of cum in you. The only things better are sucking another cock while being fucked or taking two cocks up your ass at the same time. I've been a cock slut for many years and have taken many thousands up my ass, sometimes 40-50 a day and still wanted more. Keep progressing.
Anonymousalmost 12 years agoThe dimensions of penis depicted in your story is actually not so easy to conceal - difficult to pull back and tug securely between the legs. Alright if you're wearing tight pants over but not so if you want to be adventurous and wear a swimsuit of any kind in public. I'm talking from experience!
I quite enjoy your story as I also bought my first butt plug on my way to work. The only difference was that I couldn't wait till the end of day and had to put it in place in the toilet stall and then prenteded to work through the day in the office, feeling... I recommend that you try it.
The only constructive advice I would offer is proof read before submission. Now I'm going to read your second installment.
