joranc
Member
Posts: 762
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#1 · Edited by: joranc
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thats avery interesting story tim , thanks for sharing. i am not a sissi and have no desire 2b but i cant help wondering at times if this is where my wife would picture me in say 20 years.. but that would be ssified tru ?(omg and wat a sight that would b)
you Tim UK however are a tru sissy, and i am sure u r your wifes bestest friend.
name
is that really true?? or
droll conversational banter from the professor ... C: ) + *: ) = ��
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joranc
Member
Posts: 762
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I wanna be much more like you
Your effortlessly graceful scene
That drips from every pore of you
Where logic cannot intervene
I wanna take a bath with you
And wash the chaos from my skin
I wanna fall in love with you
So how do we begin ?
I wanna be a girl like you
The way you swing your hips in jeans
I wanna wear my face like you
Shiseido MAC and Maybelline
I wanna paint the town with you
And tickle you until you scream
I wanna fall in love with you
I wanna say I do
I wanna be much more like you
The way your smile lights up the room
I'll kick back as men flirt with you
To jealousy I'll stay immune
This confidence in me and you
This hope that you and I will bloom
I wanna fall in love with you
I wanna say I do
The question is do you ?
nice misterg..i do.. placebo.....thought it would fit here?
do you listen to music when dressing up?
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sissyannie
Member
Posts: 30
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I just start wearing panties and can not stop.I wear more and more women clothes all the time
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zoyboywonder
Member
Posts: 29
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When I was about 10 or 11 I had a few hours alone in the house, a rare occasion. I spent the time in the bathroom playing with my sister's curling iron and make up. I indulged my hair fetish as often as I could, hot oil, henna rinses, curlers, crimpers, lipstick and eye make up. I loved the feel of powder on my face. I probably started trying on women's clothing about then. The first time I ever released was accidently. I found a stash of an older brother's porn. I read a story about two guys being powerd to wear pantyhose, face each other, roll down the pantyhose, and rub cockheads together until cuming. I was scared i didn't know what had happened. I had no idea cum came out like it does. How's that for proof of being born a sissy?
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everyday20072007
Member
Posts: 3
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first time i wore them in front of a woman was when I begged my wife to have fun with 2 men who was camping beside us in the mountains. jame
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Little Boy
Member
Posts: 82
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Hi 'Susan',
I don't know what exactly triggered the idea of putting on my lady's panties, but when I did I fell in love with the feeling. I must have been 13yo, my lady would have been about 33, I'm now 38. Almost her entire collection of panties consisted of what I guess we call granny-panties now.
That smooth nylon against my peepee, just felt so wonderful. To play with my peepee, I would put on a pair of her panties, pinching a little of the material between my thumb and index finger, I have a little vagina of nylon.
Pretty soon after my first encounter, I found that sniffing, even licking, her soiled panties while I played with my peepee in another pair of panties just made the whole experience so much more powerful.
It got so I'd rest between cums, staining my lady's panties with pre-cum before pulling them down to I shoot onto my stomach, but then I'd be at it again... oh to be young again Once I had satisfied my desires, I'd toss the now stained panties in the dirty clothes, but I kept lady's soiled panties in my bed, under the sheets. Who knows the reamistering behind that
Within 3 or 4 months, my lady confronted me with the fact that I was stretching her panties and since I wore a clean pair of panties every time I played with my peepee then threw them in the laundry, she would run out panties very quickly. She said she'd give me a couple pairs of her panties to "play with" as she put it. She was going to allow me to pick 2 pair from her panty draw, but I pleaded that I think 3 pair would be better. I'm sure that if she had said 3 I would have begged for 4 ;)
As I was looking through her panties, taking my time because it was so exciting to have my lady there with me, even though I already knew what 3 pair I'd pick. As I was picking up each pair to "examine", my lady would explain what she liked about those panties. When I picked a pair, she'd ask me what I liked about them. I was going to pick 3 white pair, but she suggested "something a little more feminine". I ended up with something like pastel pink, beige and a tiger print. All my previous experience with "my" underwear was that they were all white!
Once I selected the 3 pair she marked them in the label with a marking pen. She said that it would be better if I didn't toss the panties in the laundry every time I stained a pair. Maybe I should let a couple of days or week of stains build up before putting them in the laundry. That way I would always have a pair "play with even if she didn't get around to doing the laundry right away."
She never mentioned the word masturbation. She never said anything about me "going through a phase", I "needed a girlfriend" or the such. I think she knew that I was a sissy, although she never said the word until I was older.
She also never said a word about the soiled panties she'd find collected in my bed. It was a stop she'd make when collecting the laundry. Even if she wasn't changing the bedding, she'd come into my room (never when I was playing with my peepee at least until I was older that is) pull back the sheets, take the soiled panties she always found and add them to basket. She would do this with or without me in the room. If I was in the room, she'd just look at me with a smile. Sometimes saying things like, "my we had fun haven't we?" Or if she found an especially soiled pair of panties (I rarely put on her soiled panties back then) she would giggle and say, "you really like 'em this dirty?" I'd nod my head and she'd said "OK." I don't recollect if her panties got any more soiled, maybe she wouldn't wear a panty liner as often.
Sometime later, I think a couple of months, out of the clear blue, my lady said we needed go shopping for panties for me. Panties my size and that I could wear all day, every day. Initially I thought she meant boys underwear, but in the car she said something to the effect, "I know a lady at a lingerie store that will help us get panties for you. This lady understands little boys [hence my handle] like you." I asked if I had to give back the panties she gave me, she thought that hilarious. She said that I didn't have to give them back, plus there were pretty well stretched when she looked at them as she did the laundry.
I ended up getting something like 7 pairs of panties ("one for every day of the week," said the lady at the lingerie store), 2 girdles ("every girl needs a good girdle or two"), a couple of bras and slips. Initially I was unimpressed the girdles and bras although the slip felt heavenly between my fingers. My lady said that I should have the all the lingerie a girl of my age had, especially if I wanted to wear dresses. I nearly fell over when my lady said that. We kept a few pairs of boy underwear, in case of emergency as my lady said.
When my lady determined that my "play panties", as they came to be call, had worn out (from lots of playing ;) she would say it's time to pick out another pair. My "play panties" were always a pair of her panties, not something brand new we bought at the lingerie store. Maybe on the 2nd or 3rd replacement, my lady thought I should pick from her soiled panties instead of her clean panties. We collected all her soiled panties (mostly from my bed), put them on her bed and I'd select a pair. Of course they would the dirtiest pair, if they weren't my lady would direct my eye to a pair she thought was more soiled. I think my lady had figured out that if I got a "play pair" that were already dirty, I wouldn't be so ready to toss them in the dirty laundry... smart woman.
Anyway there's more... but you asked how and when I started...
XO
LB
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drdneast
Member
Posts: 1281
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What beautiful stories. Mothers can be so supportive for a young boy discovering his sexuality. I also started wearing panties when I was young but more around the age of 9. My sister was a few years younger than me but we were both around the same size and I liked the way her little cotton panties felt on my body. My mom eventually bought her some satiny ones and it felt like sheer heaven to put those on. My sister soon complained to my mom that I was streching them out so my mom told me she would buy me some of my very own. The first time she helped me put them on was shear exctasy. Although I couldn't squirt at that age, I remember getting very nice stiff errections whenever I put them on. My mom also bought me some nice nighties and sometimes on weekends we would have makeover parties where my mom would do my sister and my hair and makeup. I remember having my first ejaculation in a very sexy pink satiny pair of panties my mom had bought me. I was in bed early in the morning rubbing my penis between my panties and the bed and suddening my little penis started throbbing and squirting out my little boi spermies. It felt so wonderful but I was scared about what it was so I called for my mom and asked her what had happened. She looked inside my panties and just smiled looking at the mess I had left there. She explained to me that I had had my first orgasm and asked if I had enjoyed it. When I told her I had she told me it was very normal for little boys to start squirting and that whenever I felt the urge to come into my room and take care of myself.
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lolli
Member
Posts: 5
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drdneast and Little Boy,
Thank you so much for your postings. Those stories are so wonderful. It is great that your ladys are so understanding and supportive. Did they do other things to help you on the path to becoming a sissy? Like buy male pornography for you, or take you out to meet men? How did your sister respond to your being a sissy, drdneast? Please post more stories.
Love,
lolli I AM a girl! My ovaries are just on the outside. :)
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sissiboy
Member
Posts: 36
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I started dressing in my ladys clothes when I was about 11 years old. She was young and pretty but was single and had two jobs so I spent a lot of time on my own, dressing in her undies and then progressing to dressing fully.
One day when I was 13 I got caught by her boyfriend who was about 40. I was really embarressed but he was ok and said he would keep it a secret from my mum and not to worry about it. He started coming round when she was out and I would dress for him and we ended up becoming lovers. He bought me clothes and we continued to see each other even after they split up.
By the time I was 14 I was a confirmed, if a little confused, sissy. I later found out that while I thought my mum had no idea, she knew all along and wanted to give me space to experiment.
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Little Boy
Member
Posts: 82
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Thank You Tim!
Indeed your lady was/is? a wonderful woman, Sissyboy, for allowing you to find yourself. Does she have any involvement in your sissiness nowadays?
Thank You Lolli!
My lady didn't buy me any porn or hook me up with any men per se. But she did facilitate my further sissification in all manners of way. For example...
Mother now began giving me regular weekly enemas every Thursday. In the past she had given me an enema when I was constipated or ill. Initially I wasn't enthusiastic about getting more enemas. I said, "I'm not sick," she said, "it doesn't matter, being clean is more important." This from a woman that thought it OK that I played with her soiled panties ;) At the time, I didn't understand what she meant. With the new weekly regime, Mother had gotten new equipment, the nozzle was shaped with a big head and thin neck (a butt-plug... but I didn't know the proper name just yet), "so it won't slip out." The fluid container was larger than the old hot-water-bottle thingie.
Mother changed how she dressed for the occasion ;) With previous enemas, whatever she was wearing at the time was OK. On most week nights, lady would change out of her business suit (jacket, blouse skirt, pantyhose and heels) as soon as she got home, but on Thursdays, she just took off her jacket. After dinner, she would call me into her bathroom. I was wearing only a pair of my panties, she had taken off her skirt, keeping on her blouse, pantyhose and heels. To lube me she had me lay face-down over her legs which caused my butt to stick up in the air. Mother changed her "lubing" technique, she seemed to use more KY jelly, making sure to lubed up and down my crack, push KY jelly into my butt-hole with first one finger, then two fingers. Once her fingers were in my butt, she would roll them round, messaging (what I now realize was) my prostate. After she was "done" with that, we began the cycle of enema, hold, expulsion and re-lube.
It only took a couple weeks and I was looking forward to Thursday nights. I loved feeling my peepee rub against her pantyhose, in fact with the prostate message and the nozzle inserted into my butt, I'd dribble loads of pre-cum, leaving wet spots all over the thighs of her pantyhose. At the time I never understood how I made a wet spot in the panel of her pantyhose ;) I soon realized that that wet spot was what caused the cotton panel of her panties to become soiled. I'd now be seeking out Mother's pantyhose to see if the panel was deliciously soiled. I loved the enemas, I asked for extra fluid to hold, to hold longer and for more cycles. We usually did three cycles but every now and again we'd do a fourth cycle. I also wanted to feel a larger nozzle. I asked Mother if they made a nozzle with a larger, more massive head. She said she'd look into it.
That desire for a larger nozzle fed into other desires too. At some point during my peepee and panties play-time, I felt something was missing in the experience, I wanted to slide something in my sissy-pussy (of course this is me looking back on my feelings and motivations - I'm sure at the time I was going, "Jeez I need to be filled"). So, when Mother found a number of candles of various lengths and diameters in my nightstand, she asked what I was doing with them. Embarrassed... I sat on the edge of my bed looking at me feet. She broke the ice, "was I putting the candles in my bottom?" I nodded. Not ready to give me any relief from my embarrassment, "was I inserting the largest candle too?" Another nod. "Isn't that uncomfortable?" Finally I just gave up and said that it felt good when I put the big candle in my "bottom" and I played with my peepee. She smiled, "OK as long as you're careful."
The following week, as I recollect, Mother asked me to bring my candles into her bedroom and spread them on her bed, from thinest to thickest. She took a brown paper bag from the top of her vanity, pulling a variety of rubber things; they were various lengths, various shapes and various diameters (I measured 'em once but don't remember exact sizes now... my best guess). The two smaller items were pink/skin tone and the larger were black. There was a long, thin-ish (8" x 1 1/2" dia) dildo with balls at the base. There was a butt plug shaped like a cock (6" x 1 1/2"). There was a barrel shaped butt plug (5" x 3") with rounded top. The large dildo was 11" x 2 1/2", a little larger than the largest candle. Mother said it might take some practice getting used the larger "toys".
I wanted to try my new toys right away and was about to leave her bedroom, but she surprised, shocked might be a better word, me. She wanted to see if I could insert any of them, volunteering to get the KY jelly and a couple of towels from the bathroom. Granted she had been doing roughly the same thing giving me an enema, but this was some how different. I realize now that she wanted to make sure that I didn't hurt myself in my enthusiasm to try the toys. We tried the small butt plug first, there was no problem. She asked how it felt, I said it felt nice, to which she replied maybe I should try keeping it inserted over night some time. My little peepee was jumping around with the idea of doing something so "nasty". Not that what my lady, grandlady (at least a little) and I had been doing over the months wasn't "nasty"... at least to some people.
Mother actually used the words "butt-plug" and "dildo", saying they are the proper terms and that's what I should call them. I don't know what I was going to call them but now I knew officially ;) So we had the pink butt-plug, the pink dildo, the black butt-plug and the black dildo. After I had the pink butt-plug in for 10 or 15 minutes, she said "we" should try the pink dildo. That slipped in without a problem, after all I had been stretched with the plug. I couldn't insert it all the way. Mother said don't power it, I needed to train my body. She said, "let's see what you can do with the black butt-plug." She explained that I, "would find out that black sexual things were always bigger than white... er pink." Another inscrutable statement from Mother... at the time.
The black butt-plug was scary, which made it exciting as well. She bent me over to re-lube my little bottom with additional KY. She coated the plug placing it on its base on a towel on the floor. She had me get on my knees so my bum-hole was right over the top of the plug. She said I should try sitting on the plug while trying to poop. This sounded dangerous given that I might actually poop, but did as told. I began to drop my butt onto the plug while pushing out. I could feel the rounded end begin to slide into me. It felt huge and I began to breath a little fast, Mother said slow down and concentrate. My poor little hole was now stretched to the full diameter and I was continuing to drop my butt on the plug. I had no idea how much more there was, when Mother said stop and just relax. It was odd, it was uncomfortable but it also felt incredible at the same time. After maybe a minute, I decided to drop a little more Mother said that was good enough for the first time and I should pull myself off the plug. That was very easy and when I was completely off of it Mother showed me how far I had gone, nearly to the point where the barrel drops to the neck.
Next was the the black dildo. That went in even easier that then pink dildo but again I couldn't get it inserted more than half way. More training was called for... and I was just the sissy to do it ;) Mother said I could go, and I scooped my new toys. Mother said she was going to throw away the candles. When I got back back to my room I slide the pink plug in my sissy-pussy, dug out a couple of pairs of my lady's soiled panties, put on my "play panties" and had a mind blowing orgasm. It still remisterates when I think that first butt-plug orgasm!!! In another week, with Mother's help, I was regularly inserting the black plug, but I couldn't hold for more than 10 or 20 minutes. Mother said that wasn't anything to be ashamed of and I should just keep at it.
I was going to tell how, when I was a little older, Mother would orchestrate situations where the opportunity for some guy to come onto me occurred. But I ran out of time... maybe later.
XO
LB
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sissiboy
Member
Posts: 36
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Hey LB please tell us more. You were so lucky to have such an undertanding mummy. Mine didn't do much beyond giving me plenty of room to develop my sissyness. It was the mid 1970s and and fashions were pretty androgenous so my mum used to buy me things that were a bit girly, which led to me being teased as a sissy a lot, but of course you get used to it.
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shawna
Member
Posts: 495
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My lady was the complete opposite. I grew up in a female dominated household. My man worked on the road and wasn't around very much at first, then they were divorced when I was seven. It was just me and my two sisters, one older by 4 years, the other younger by two. My lady was a firm believer in corporal punishment, making it very ritualized. Spankings were always scheduled ahead of time...if one of us misbehaved, she would tell us that we would be punished after supper that night, and they were usually done with all of us present. We would be called into the living room, where my lady would be sitting in an ornate straight backed chair. In front of the others, the transgressor would have to repeat whatever it was we had done, then would be sent to my lady's bedroom to "fetch the brush", an old-fashioned, large wooden hairbrush with a long handle and smooth, flat, oval back. The spanking was always bare bottom and over her lap. The spankee would have to count each stroke, then mandatory corner time with pants, or panties, around the knees.
She pretty much stopped spanking my older sister when I was nine or ten,
and because I began to exhibit the natural urges of a boy my age, I would not be present if my younger sister was being punished, but since she was the "baby" of the family, she got away with a lot more than I did. This, however, did not prevent my lady from requiring that my sisters continue to be present for my punishments, which began to happen more and more, sometimes 3 or 4 times a week. In addition, after telling the three of them why I was being punished, I would retrieve the hairbrush from it's place on her dresser, then be made to strip naked before lowering myself over her stockinged thighs for my spanking. The offense of this in, in front of my sisters, was extreme. After counting off the 15 or 20 strokes, I would have to stand naked in the corner, my red bottom on display, for 30 to 60 minutes while they went about the usual routines, tv, homework, getting ready for school the next day, etc.
I was still sharing a bedroom with my younger sister at this time, who began to tease me about getting spanked in front of her. When I complained to my lady about this, she said I deserved it, that if I wasn't such a bad boy who constantly misbehaved, I wouldn't have to be punished. This resulted in my sister telling on me or making up stories about things that I had not done, and the spankings grew more common, almost daily. This pattern continued for a another year or two... i would sit at the dinner table and listen to the giggles and insults from my sisters, how they were looking forward to watching me get my punishment later. that I was such a bad boy who needed to be spanked all the time.
When I was about 12, puberty started and I began to get the inevitable erections from all this erotic offense. They would laugh at me as i stripped to reveal my little hairless cock, stiff and proud. My lady acted as if it was totally natural, and had no problem explaining to my sisters that little boys like me sometimes got excited from a spanking. I don't know what experience my older sister had at this time, but she would laugh and comment on how small I was. My lady would pull me down over her lap, toes on the floor, head hanging down, penis trapped between her thighs as she spanked me. This was how I had my first orgasm, and when she realized it, she called me a filthy, nasty little boy and spanked me as hard as she ever had. This resulted in a new ritual...before going to "my corner", I would have to apologize as I wiped her thighs, and the floor, with a towel while my sisters looked on.
Now in my early teens, I was surrounded, and pretty much subjugated, by three females at home. My lady was in her ealy 40's at this time, tall, dark-haired, with a full figured body, almost the classic "Marilyn Monroe" type. She was a mid-level manager for a national delivery company, and wore the typical early 80's power suit to work. She favored somewhat old-fashioned lingerie, heavy bras (she was pretty busty) corsets and girdle-type panties, or full one-piece support garments, always thigh-high stockings clipped to the attached garters. My older sister, now approaching high school graduation, was an opposite, tall, slim, sandy brown hair with smallish breasts and long legs. Thongs, skimpy little bras, and the early 80's Madonna look, lots of lace and jewlery, was her usual outfit. My younger sister favored my lady, darker and curvier, entering an early puberty. She had more of a tomboyish look, short-shorts or minis and cute little tees. The reamister I bring all this up is that since it was three to one, and I was often naked in front of them , they had no problem with semi-nudity and even occassionally being naked in front of me. The hampers were full of panties, the bathroom always had stockings hanging off the towel racks, the clotheslines were full of all types of feminine clothing. I know, because doing most of the laundry had become one of my chores. My younger sister complained about sharing a room with me, so my lady converted what had been her "sewing room" that adjoined her bedroom into a room for me. I complained about this, but she said that little boys didn't need as much room as girls and she could keep a closer eye on me this way. I burned with shame as my sisters taunted me about being a "little mama's boy". I had almost no privacy as she wanted me to keep the door open between our rooms most of the time, and I often saw her naked after a bath or slipping out her clothing to go to bed. My sisters were more blatant about it, walking around in skimpy clothes or their undies, calling me in while they were on the toilet or bathing and then laughing at my embarrassment.
Because I was constantly humuliated when exhibiting any excitement over their bodies, I began to fixate on their underwear, especially my lady's complicated, restrictive things. By this time, she would remove her dress or outer clothing before administering punishment to me. I would be dizzy with excitement at the sigh of her wearing heels, thigh-highs and a black, heavily-boned one piece or girdle and bra, her breasts spilling out of the cups, hairbrush in one hand while pulling me over her lap with the other. Since I did most of the laundry, I handled all these things any way. One Saturday night, both my older sister and lady were out. My younger sister was doing something in her room and everything seemed quiet. I opened the drawer to my lady's dresser where I had placed the neatly folded garment earlier that day, and quietly went into my room and shut the door. I stripped naked and began to pull the black one piece on. The lycra was heavy and tight, the boning stiff and unyielding. As I worked it up my body, my little dick was straining with excitement. I finally worked the straps up over my shoulders, and realized that although I was almost as tall as my lady, I would never fill out the cups...they lay flat against my chest. I needed something to stuff them with...some panties or stockings, I thought. Flush with excitement, I opened the door and went over to my lady's dresser, opening up her panty drawer. "You just wait until I tell Mom what you're doing!", my sister screamed from the doorway, before running off to her room and slamming the door behind her, laughing all the way. And that started a new, more humuliating and painful chapter in my development. My sister did tell my Mom, I was powerd to put the one-piece on and stand in abject misery before all three of them, then "fetch the hairbrush". The spanking I received that night was long and hard, because my bottom was covered with the thick material of my lady's girdle. I soon became not a bad little boy, but a bad little girl, and the supply of women's clothing and undies in the house increased quite a bit.
Sorry it took so long, but that's how I got started...mostly...75% truth, 25% fantasy!
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dannyokla
Member
Posts: 151
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wow sometimes i read things and realize people are used, and do not know it
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shawna
Member
Posts: 495
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who says I don't know I was used?
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drdneast
Member
Posts: 1281
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My first time with a man was with one of my ladys bf's. I had spied on them before and knew he was fucking my mom. One night he came into my room and started to talk about sex which got my little penis very stiff. He could tell I had a little hard on and asked me if he could see it. I pulled my shorts off revealing the pretty teal colored panties I was wearing underneath. He whistled and told me how sexy I looked. He asked me if I wanted to see his cock and I breathlessy said yes. He dropped his shorts and his thick cock sprang out all lewd and excited. "Go ahead and touch it, I know you want to and I want you to." I tentatively reached out and stroked his penis like mine and he moaned with pleasure. He then guided his cock to my mouth and told me how sexy I looked with my panties on as he started thrusting into my mouth. When he squirted he pulled out spraying his hot seed all over me. After he finished he got down and slid my little penis into his mouth and got me off very quickly. He continued to play and fuck me for about three years afterwards in a very loving manner.
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jeff philips
Member
Posts: 1
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My Wife led me into being a sissy she persuaded me to dress up in womens clothes for a fancy dress party somehow once I was dressed up her attitude to me changed and I felt very submissive.
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mona
Member
Posts: 87
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Hi all,
Some great reads here. I'm 52, twice divorced and presently on disability for 2 weeks cause of torn ACL. Stuff brings back yummy memories of things in the closet. What is it about bbc!? ;)
Mona
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Elise Povall
Member
Posts: 36
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