I hope you enjoy it, please feel free to post your opinions and thoughts, however be gentle and I really am a nice guy..
Where does my story begin?? I guess it starts with the first time I found a pair of my mom’s nylon undies.. I was about 8 years old and was exploring my Mom’s bedroom and stumbled upon a pair of her underwear and to my surprise, it wasn’t the same as mine.. Her’s was slippery to touch, much softer and I enjoyed the way they felt in my hand. To this day I still remember how good it felt and how even at the age of 8, I developed a little hard on.. Of course, I was too young to know what to do with my new found friend, but it sure did feel good!!
I don’t remember what happened next, but I do remember wearing them under my normal clothes and somehow we ended up at my Grandma’s house. I don’t recall the particulars, like why we were there or how long we stayed there and even what I did while I was there, but I do remember walking out the front door of the house, my Mom and Grandma walking behind and my Mom asked aloud if I was wearing her underwear.... ??? I don’t remember answering as I just remember running down the sidewalk, running thru the open gate and feeling some what embarrassed. Silly me, I should have known better, because I had ripped a hole in the seat of my pants and the panties were clearly visible..
As I progressed in age, my next memory was while living at my Dad’s house for one summer, I was staying in a little bedroom that was built inside the garage. While snooping thru the cabinets and shelves in the garage, I stumbled on my Step-Mom’s clothing she had packaged up to donate to Goodwill or the Salvation Army. Inside the shopping bag was various women’s items and even some of her old under garments.. As much as I can remember, the shopping bag of clothes was in the garage for several weeks and I visited them as often as I could. On the day she was to actually donate them for charity, she asked me if I had rummaged thru the bag, because all the clothes were once neatly folded.. Of course I put on my little innocent halo and denied even knowing the clothes were there.
Later on in my teenage years, I guess I was 16 or 17, I moved to back to Mom’s house for a little while and my younger sister was growing into a real hot little babe.. Looks wise, she had it all going on... She was 2 years younger than me, but she was quite often in my fantasy while masturbating. She stood about 5'2, probably in the low 100 lbs range, blonde hair, nice perky tits, nice round tight ass and smooth silky tan skin.. No doubt, she looked really sexy when she got all dolled up.
I often raided her underwear drawer and laundry basket. Most of the time, I would take two pieces of underwear. One to beat off with and one to put my head inside and smell the sweet sweet smell of her pussy. Man, I cant tell ya how many times I shot my load with my nose in the crotch of her panties.
Also, this was the first time I explored the world of wearing pantyhose. The softness of the material as it slid across my legs was pure heaven... I was either too tall, or she was too little for me to actually put on all her clothes, but I did walk around the empty house wearing her panties and pantyhose. That feeling of the legs rubbing together when I walked was is just so damn erotic to me, I instantly got hard no matter if I had already cum or not.. Unfortunately, we have to grow up and those erotic days have long since passed and are just a memory to me.
Several years later I got married to a cute little lady and my need for wearing soft smooth and silky women’s wear never really went away. Due to the guilt and fear of being called a pansy or a ***, I forced the desire of wearing my wifes clothing out of my head. Those were nasty, perverted and sissy thoughts, had no room for my macho self... But deep down inside, I felt the tingle... the passion and the thrill of looking at and feeling ladies undergarments never completely went away.
During my weak times, both myself and the wife worked, however I got home about an hour or so before she did and for as far back as I can remember, I found myself rummaging thru her underwear drawer and the dirty laundry hamper, searching for those soft, silky nightgowns, slips and underwear. Nothing was safe from me, anything soft and silky would eventually end up wrap my dick with me beating off until I came.
10 years into the marriage our sex life started to get stagnant. I mean I was still in love with my wife, our future together was still growing, but the excitement and the passion quickly left the bedroom. We both knew each others bodies all too well, so there was nothing new to explore or find. Usually, I would just roll over on top of her on Saturday mornings, do my thing and then continue on with our lives and routines.
Then somehow... and I really don’t remember how it got started, but wearing her lingerie was introduced. The passion and the enthusiasm was back in our sex life.. Its funny how something as silly as a pair of underwear can change a marriage..
Deep down inside, I wanted to progress further.. I wanted to wear more, I wanted to wear everything, I wanted to feel and look just like she did when she dressed herself up. I wanted to grow a vagina and I wanted to have her grow a dick, I really wanted to feel everything a girl does and most of all, I wanted to know what it was like to have her stick her hard hot throbbing dick deep down inside me.. That I believe has always been the root of my fascination. I know what its like to be on the outside going in, but I wanted to experience sex from the inside. I can only imagine what it feels like to have your pussy stuffed with 6-8 inches of hard hot cock.
Sometimes, while rolling around in bed, I would often lie on my back with her on top of me, my dick is inside her, but my legs are spread wide apart, her legs were held tightly together and she would do the up n down motion while probing the inside of my mouth with her darting tongue. I came many times this way hoping and wishing the gender roles were reversed.
As we progressed with the wearing of her panties, or whatever it was we were doing back then, her and I never really opened up and communicated our hidden secrets. Even with my heart almost pounding out of my chest with excitement, I always kept a cool front, a reluctant attitude about wearing her clothes.. I guess I still felt the guilt of “crossdressing” and the gender role reversal, aka the “GAY” thoughts I had. However somehow I was able to silently and passively get her to agree to a night of full on gender reversal. Maybe it was me that talked her into it, or maybe it was her that talked me into it.. I really cant remember, but for a solid week, we planned for one evening of pure uninhibited role reversal SEX..
She spent every evening right after work shopping for “my” costume while I had be the brave one to visit our local adult bookstore to buy the dildos, lubricants and stuff. What she ended up buying is this very attractive bra, panty and garter set. The bra was pink in color with black lace trimmed around the edges. The matching panties and garter was identical and I still get a tingle thinking about how sexy they were. In addition to that, she bought black nylon stockings, the one with the black line running down the back of the leg and she also bought this see thru black frilly robe that went down to just slightly below the panty line.
I ended up buying an 8" vibrating dildo and a double headed dildo which ended I ended up using on her during the week. I remained cum free for the entire week, but the excitement and anticipation of our new toys got the best of us, so I used them on her at the end of the day. I used both dildos on her, but I liked the double headed dildo the best. When I stuck it inside her pussy and when she closed her legs together, it looked like she was equipped with her own dick. I would jack off the dildo as if it was a real dick and she came over n over many times that week.
Ok so Saturday finally arrived, I had to work on this day, but the wife had the day off, so I told her to take a shower and wear my new pink black laced panties around the house all day to get them good and smelly, which she did. After work and as night began to fall we were ready to start our night fun.... I went into the bathroom to take a shower, cleaned every square inch of my body, shaved my legs, arm pits, chest hair and neatly trimmed a little girly patch of pubic hair thinking I would look just like a girl would when I put my dick in between my legs. After drying off with what else... a pink towel and applying that body powder stuff that comes in the round pink container with the fluffy pink ball thingy, I then put on the wifes pink robe while completely naked and walked into the bedroom. She was in there laying on the bed watching a lesbian porn video that was playing on the VCR. She hit pause and walked towards me to greet me with a huge, wet and very sexy kiss which included me being the receiver of her tongue as she explored my mouth.
We both then walked back into the bathroom where she had me sit at the make-up table, where she applied make-up, eyeliner, lipstick, the whole nine yards. I told her to make me look like the female slut I was about to become. She also put on those tape on fake fingernails that are painted Hooker Red. Once complete with applying the make-up and trying to make me look as sexy as possible. She went into the bedroom to get dressed while I stayed in the bathroom. She handed me the lingerie and the pussy smelling pink panties and told me to get dressed, she also surprised me with a blonde log wig that she bought from the Halloween Costume store earlier that day, which really added to role playing. .
The clothes we set out for her to wear was nothing exotic or erotic. First she slipped in the double headed dildo, slipped on a pair of white cotton briefs, that was too tight for me, she wore an old pair of Levis and a button up flannel shirt.
I on the other hand, was inside the bathroom getting all “dolled” up. I also had an erection that wouldn’t go away.. The entire time from taking a shower to shaving my legs to putting on the make-up I don’t think I ever lost my erection... I remember that I trembled and shook as I slowly started to slip on the first stockings, one leg on the ground, the other on the edge of the sink as I slowly and as sexily as I could, slid them up my legs with the red fingernails. I don’t know how you women do half the things you do with fingernails on.. They really do get in the way... Finally after putting on both stockings, clipping the garter straps in place, I put on the bra, the cups were a little empty, but the feel of slipping the bra over my shoulders was very feminine. Next was the pink smelly panties and a quick look in the mirror I saw a pretty sexy little body that I would fuck if it wasn’t me.. I slipped on the wig, put on the black see thru nighty or robe or whatever its called and did a final check in the mirror and quick brush of the hair. I then gave our little code of 3 knocks on the door which meant I was ready to come out.
A second and a half later, she told me to come on out and as I opened the door, I saw that she had turned off the lights and TV, lit several candles and put on some soft music in the background and then my eyes focused on her.. I mean him..
He was sitting on the edge of the bed, wearing a flannel shirt, greased back hair, a pair of Levis and I was able to see the budge in her pants as she stood up. I walked towards her and once again she greeted me half way with her arms out stretched which she quickly wrapped around me, however she was a little rougher than before. She once again gave me a real passionate and sexy kiss. She turned me around and pushed me softly on the bed. I was on laying on my back with my legs hanging over the edge of the bed as she crawled on top of me kissing and rubbing her hands all up n down my body my sexy body. Her mouth found my mouth and we kissed with passion and excitement and I was easily lost in this passive fantasy. Her kisses went from my mouth and eagerly parted lips, to my neck and down my chest where she was biting my nipples thru the material of the pink bra. I’m sure it was an awkward feeling for her, as I didn’t have the soft spongy tits a real woman has, but it sure felt good to me and shot tingles thru out my entire body. She continued down my stomach, licking and kissing her way down. As she reached the top of the garter belt, she was kneeling on the floor with her body between my legs, she lifted one leg up and started licking and kissing my calf thru the black nylon stockings. As her kisses moved up my leg and just before she got to my pink panties, she pushed my legs apart as far as she could and she dove right into the smelly crotch and started rubbing her nose all over, licking, kissing, nibbling and scratching her fingernails up n down my legs, feeling the soft nylon material. Her hands also moved up my body, reaching my bra and playing with the nipples inside. Then her hand would run across my soft stomach and the whole time, she never once moved her mouth from my crotch. After giving me all this pleasure and attention, I was ready to cum.. I wanted to shoot my load all over her.. but instead, I told her that I needed to stand up.
We’re both back standing on the floor, standing next to the bed and facing each other. I grab her this time and force my tongue down her throat as far as I could reach while my hands started to explore her body.. I caressed her butt, her shoulders, arms and eventually made their way to her crotch, where I found a huge hard dick like bulge in her pants. I slowly step back and started to unbutton the flannel shirt. Running my red fingernails up and down her bare chest as I go. I then drop to my knees and kiss her belly and slowly start to unbutton the Levis, while running my fingernails over the bulge of her hot, hard cock. Once unzipped, I let the pants easily fall to the floor and now I push her onto the edge of the bed.
I look down to see this rock hard cock, trying to tent up in the white cotton briefs as I slowly run my hands up n down its shaft while its still inside the underwear. I start kissing on her inner thigh, moving slowly but surely closer to her package. I bury my nose into the base of her dick and start licking and running my mouth over the shaft. I was quickly getting excited with the anticipation of finally being able to suck on a cock in between someone’s legs. At the same time, I had a flash of guilt knowing that this will lead to deeper and darker desires and that I could stop now and nothing much would have changed. But the desire to wrap my lips around her cock was too great and I slipped my fingernails into the waistband and slid the briefs down. To my surprise, the cock springs into action hitting me in my face as I grabbed it by the shaft and slowly slid my hand up and down savoring the vision of my red painted fingernails sliding up n down this hard cock.
About every 3rd of 4th stroke, I move the dildo in and out of her just to keep her as excited as I was. I then slowly open my mouth and lick the tip of the head. I wondered what it would be like to taste pre-cum as I slowly kiss the head of her dick. My mouth and tongue kept sliding up n down the shaft making sure I paused at the bottom to do some special licking on her.. Then I take the dive, I open my mouth fully and go down on the cock for the first time feel of giving a man a real blow job. By this time I’m horny as hell and all my inhibitions are gone, I really start sucking on her cock. With my hand wrapped around the base and with my mouth taking as much as I could, I start bobbing my head up and down, pulling the dildo in and out of her as I go.
I look up to see her resting on her elbows watching me with lipstick painted lips wrapped around her cock and everyone in awhile she moan aloud which told me I was doing something right. I tried to remember what girls have done to me while sucking my dick and of course I tried to duplicate it, but the one thing I quickly realized is.. I like giving head, I enjoy having a dick in my mouth and best of all, I like sliding the dick in and out of her pussy bringing her to orgasm. The only thing that could have been better was to feel the texture and taste the taste of real sperm in my mouth, down my throat and dribbling out the corners of my mouth.
After her orgasm subsides, I then crawl on top of her, straddling my legs on both sides of her and we embrace in another deep passionate kiss where I roll over and she is now on top of me with her dick sandwiched between us. Her hips pushing into my crotch in a dry humping fashion. That was pretty exciting and if fueled the passion in our kiss.
She now lifts her head as I look in her eyes, she mumbles the words “I love you” as she slides down towards the bottom of bed. She tells me to lift my hips and helps me take off my cherished pink panties which has just release my hard throbbing cock. The freedom of being out in the air feels really good and the Mrs wraps her lips around the head and starts sucking on it. She then works her mouth and tongue all over my dick, paying special attention to my balls and scrotum. With my legs spread wide apart, she carefully slips a pillow under my butt and then takes her dick in her hands and reaches for the jar of vasoline. She scoops out the petroleum jelly with her fingers and starts to jack off her dick, getting it all nice and slippery. She then points the head of her dick at my crotch and lovingly rubs it back n forth against my dick, my balls and the hole in which it will soon enter.
I’m laying back, head on the pillow, arms outstretched above my head and my eyes were closed as I savored the moment. I could feel her probing her dick around my opening and slowly and gently pushing on it, trying to get me to accept it. I think to myself... Ok, you’ve wanted to get fucked all your life and now its about to happen. As with one forceful push, she slips the head passed the opening of my ass and I let out a really loud and painful scream as I felt my body get ripped wide open.
Thankfully, she pulled out her big... I mean BIG HARD DICK from my ass and gave me time to recover. I was still very much excited and wanted to continue, but after a quick moment of pause I wanted to endure the pain and told her to go back in. This time she was more gentle and was able to get a good 3 or 4 inches in.
After a few minutes of having this hard hot cock inside my man pussy, I started moving back n forth which encouraged her to drive it in a little bit further. After a few slow and gentle strokes, I was opened up and wanted as much as she could give me. I don’t think it felt as good as if she slipped her dick into my vagina, but the dull pain quickly turned to excitement and I finally couldn’t hold back any longer and shot my come all over my stomach, chest, face and even both sides of the pillow I was resting on. Once finished and with her dick still inside me, we repositioned to where our crotches was buried against each other. Her legs and feet up towards my head and my legs were the same on her. The dick in my ass was now sandwiched in to the dick in her pussy and we lovingly bucked back n forth until she came.
We then got up, each went to separate bathrooms to clean up and when I came back into the bedroom, she is standing there with one of her favorite nightgowns, which she told me to wear. I slipped it on over my lingerie and we both crawled back to bed exhausted and fell asleep in each others arms.