Ten Erotic Crossdressing Vignettes

You had to have one! At first, it was impossible to get the thing over your balls and penis. How would you get such a device over your genitals with your penis so hard from the excitement of it all, the excitement of trying to stuff your penis into the contraption? Impossible! Only after masturbating to ejaculation, some lube and some difficulty trying to "wish away" the reappearing erection were you able to secure the device over your penis, still firm though half limp with semen dripping from the tip.

It felt funny. Strange. Naughty. Delightful. Immediately after finally securing the device, you had to know. How will it feel when I get aroused, when my penis is trying to get erect in that "thing" when I look at porn or get pretty and dressed in women's clothing? It was strange. Your little penis strained so hard against its pink plastic prison as you drank in your favorite gay porn. Inside it made you soar. Real men don't do things like you do, like shave your lithe body, wear makeup and women's clothing, suck cock or stuff your penis into a pink chastity device. But you do. You left the device on as long as you could, several days, in fact, hiding it from your wife in bulky boxers and avoiding letting her see you naked. You wore it underneath your clothes at work, a constant reminder what pervy femme fag you hid from everyone.

Then you had to know. One day you took off early from work to get home before wifey. Minutes seemed like hours before you finally made it home. Alone in your bedroom, fumbling with shaking hands, you inserted the key to remove the beast. Once your penis was finally free it did not get immediately hard like you thought it would. In fact, your penis wiggled limp in your hands as you tried to agitate it and incite it to erection. Fear overtook you. All your obsessing over wearing a chastity device and now that it was removed you were limp, not hard.

This was freaking you out. All the years, all your lifetime since you first discovered masturbation, all the wonderful years as a chronic masturbator who could easily ejaculate three, sometimes four times in one day, now this? You were almost in tears at this new reality. Still, you firmed up a little but way too floppy and limp to interpret as an erection. What have I done? you thought to yourself, what have I done?

You took a walk, you took a shower, you stayed away from touching your penis because you were afraid of more disappointment. Your wife asked you what was wrong, and you lied that it was "nothing". "Nothing" was what was happening down there, and it was the end of the world as you knew it. This was worse than knowing you caught an incurable deadly disease. You were so mentally exhausted by it all you actually got a good night's sleep. A few days went by, and you had to know. Wifey went to work and you called in sick. Inside you cringed a little knowing if you couldn't get hard your life would be over and you might as well commit suicide, you mused.

The moment of truth. Climbing on top of the bed naked with your laptop and a pair of panties you were soon at your favorite porn sites. There had been a few partial erections the past few days that gave you hope. Once you started seeing images of cocks, images of girls in sexy bikinis and lingerie, images of twinks sucking each other's cocks or the cocks of big manly types and you were rubbing yourself through the silky string bikini panties that familiar sensation had returned. You were hard again! It felt wonderful! On the tip of your penis a clear "tear of joy" glistened.

Such a big relief passed over you as your hand tugged on your incredibly hard penis and the gay porn was more exciting than ever. Your ejaculation when you came fiercely jacking on your penis and fingering your hole was incredible. You shot a massive load, all over your tummy. It was such a massive load you knew in advance not to waste it if it were to happen, and boy did it happen! With an empty cup from the nightstand, you scooped up all the semen for the next session. This you did whenever possible, saving the semen from one ejaculation to sip for the next masturbation. Not as good as sucking cock and tasting another man's semen but you're a perve and you don't care. Sniffing the scent and tasting semen as you masturbate sends you to another galaxy.

Having all day alone to yourself was wonderful and you waited as long as possible for the next session. This one would be even better, you knew. On the bed once again with porn on the laptop, semen in the cup on the nightstand, a pair of your wife's fragrantly soiled cotton panties you were ever so glad to find in the hamper and a sleek vibrator and some lube, you were set. The vibrator was yours, not hers, wifey never masturbated. As the porn paraded proudly in your vision and the scent of the soiled panties egged you on, you inserted the vibrator up your boy cunny and the fun began.

You hadn't been with your boyfriend for quite some time, he was married as well and getting together was not that easy, so fucking yourself with a vibrator as you masturbated was the next best thing. It was another wonderful masturbation; sniffing panties, sipping semen from your previous ejaculation and poking the vibrator up your butt. The second cummie was exasperating as you simultaneously gasped for breath as you drank in the crusted pussy scent of your lovely wife's panties in your nostrils (after swallowing all your tasty cummies from the cup), frantically masturbated and plunged the vibrator up your boy cunny.

It took many long minutes to catch your breath and cum down from this remarkable climax, cummies again all over your tummy. This time instead of scooping up the cummies, you sopped them up with the pussy scented panel of your wife's panties, knowing from experience that sniffing damp semen coated panties coupled with your wife's fragrant pussy scent would lead to another mind-bending ejaculation before wifey came home from work. It seemed like ages ago the trauma and duress you felt from the erectile dysfunction you had experienced upon releasing yourself from chastity. Now you were back to being the chronic masturbator you knew and loved, you pervy little crossdressing closet faggot. Not for long, little did you know.

This 'personal day' around the house was just what you needed. You'd ejaculated at 9:30am and again by 1 pm. Wifey would not be home again until after six pm. You showered and shaved everywhere; it had been a few days. You had masturbated to two stunning ejaculations wearing panties but really hadn't cross dressed yet. You figured if you could masturbate again by 4-4:30pm that would give plenty of time to have things appear normal by the time wifey got home.

After showering and shaving, you pulled out your secret stash of clothes. You pulled out your "drag bag" where you kept your stash of dresses, panties, bras, wigs, shoes, makeup; there is no rhyme or reason in the bag, it's all just stuffed in there haphazardly. Basically, to find something special you want to wear you have to spill everything out all over the floor to find the cherished pantie or bra or dress or wig. The only thing remotely organized is your makeup that's all thrown together in an old, zippered shaving kit bag.

You pull on some stockings and a garter belt and put on your favorite strappy high heel silver rhinestone sandals and pull on a pair of silky microfiber string bikini panties. Sashaying about in stockings, high heels and panties you tell yourself that could wear this feminine attire and only this attire, all day, every if it were possible. You envision wearing this little outfit for a room full of hairy, naked, horny men, being the sexy little tart that men love to get off on, no holds barred; no games, no dating rituals, no relationship constraints, just men in their carnal, animal lust wanting to force their cocks on you and for you to give it up so easily.

You also dream of being like this in nothing but heels, stockings and panties on vacation with a guy. Or better yet on a honeymoon with your new hubby. You'd have to be pretty damn gay to fantasize about being a man dressing as a woman to be another man's homosexual wife. But you do. All the time. You get off on this gay bridal dream, it is the number one thought that brings you to ejaculation. You're so gay, such a flamboyant little fag at heart, that a real man, let alone a husband married to a sweet gal like yours, would never have such a vivid imagination about these types of homosexual desires. But you do.

Today is special, a spa day at home to masturbate and cross-dress. Now dressed in the stockings, high heels and panties you put on a flimsy sexy silver sequin spaghetti strap cocktail dress, it's your dress, not your wife's. She'd never own or wear anything that sexy and slutty. But you do. You put on your favorite wig, a strawberry blond shoulder length number. Then you apply a little pink lipstick, some mascara, rouge and lavender eyeshadow. You look hot! Sexy! If you went to a gay bar, you'd score in minutes, most likely another married man from out of town. Married men always feel less guilty about homosexual activities with a crossdresser. "It's not gay, if 'she' is dressed as a woman, right?" or "I'd never cheat on my wife with with a 'real' woman". After snapping a few selfies and staged photos of your loveliness, it was then on to the main event, a third masturbation.

Shedding the dress, you lay on the bed still in heels, panties and stockings. On the floor beside the bed, all the panties, bras, dresses, nightgowns and shoes are strewn about haphazardly by the drag bag like a suitcase bomb that had exploded, blown up in a clown's circus act. Lingerie and female clothing were scattered all over the floor. The sexiness and femininity you feel in incomparable. Sex with your wife is a chore. Being femme and sexy like this, masturbating to luscious gay porn is the next best thing to the gay sex you'd had dressed as a woman, sucking another man's cock. You pull your panties down to your ankles so you can insert the lubed vibrator up your boy cunny. You are so very happy feeling this sexy, being so hard, the scent of damp semen across the pussy scented crusted cotton panties is driving you mad as you work the vibrator up your butt.

Images of cock and panties and lingerie and sexy women sucking cock and smooth naked sexy twinks kissing and sucking cock and huge cocks pulsating semen on faces, pulsating semen onto titties, semen onto shaved femboy penises, pulsating semen onto penises locked in chastity devices, pulsating semen up the asses of crossdressers and twinks and pulsating semen all over women's pussies and asses also. You are so happy. The damp scent of the semen on the panties takes you to another world as you plunge the vibrator, humming at full speed, deeper up your butt. Then it happens. Your frantic masturbation has produces a mind-numbing ejaculation as you are amazed that again so much semen spills onto your hairless tummy. Gasping for breath, your head spins from the excitement, the sensation, the messy climax. As you come down shaking from this incredible high, the room is silent in your repose.

In this silence you suddenly feel a presence. Standing in the doorway of your bedroom is your wife, wide-eyed in shock with both hands over her mouth. You were careless and did not think calling in sick all the way through. She was concerned about you being sick as she found out calling you at work; you only thought of the sensations in your penis. At least you were able to milk one final faggy little cummie from your penis before the rain of tears and cursing and "OMG how could you?" and "are you gay?" meant that your marriage was over and you hoped that she would not 'out' you.

TEN.

Needing some sort of reckoning with my secret life, I joined a support group, Tri-Ess. Yes it is a real group 'Society of the Second Self' that is a non-sexual group for crossdressers. For me it is perfect to be able to validate my dressing with other like-minded males and their wives (I still have not come to grips about revealing it to my wife). It's one thing to parade around in panties and lingerie alone and then masturbate. Yet being out of the closet, being dressed as a woman around other people in a non-sexual 'normal' setting is for me very thrilling. Now I'm not sure you can call males dressed up as females a normal setting, but I love it, I love expressing myself around other people 'en femme'. I have only made a handful of the meetings but each time it is more pleasurable than the one before.

The first few meetings I kept it fairly subdued not dressing slutty, just tasteful and feminine. Still, with my physique - slender, tall, lovely long legs, hottie little ass - I was a hit with the group. I wore a conservative dress, sleeveless with a banded neck so perfect for wearing a bra to give me a little femme figure. With 5" high heeled gold shoes, dark hose & a few bracelets I felt wonderful. My make up was a little crude, I just tried to look as best I could. It was a little amusing, just like being around a bunch of real girls with all the comments - "I love your dress/shoes/hair/bracelet/lipstick/purse" or "where did you get your dress/shoes/hair/bracelet/lipstick/purse?".

The whole setting is a bit surreal; a group of men dressed as females speaking in feminine voices yet supposedly straight and nonsexual. For me, I never felt gayer. The next meeting I was able to attend, I wore one of my wife's black dresses. It also was a bit conservative; short sleeves with a boat neck in stretch fabric but still very sexy on me and very short (same one I wore when I hooked up with the guy from the gay bar)! My legs looked fabulous without any hose, but I had on my wife's hot pink silk bikini panties, and I painted my toes hot pink and wore my favorite 5" silver rhinestone strappy sandals. With my "Jane Fonda" wig and a pearl necklace I looked stunning...a bit out of place really. Here I was tall, thin and very sexy in the midst of a bunch of middle-aged crossdressers built like linebackers dressed like your grandma.

Still, it was thrilling to be there, and I was a hit, everyone loved being around me. While it was supposed to be a nonsexual gathering there was a tremendous amount of sexual tension in the air. More than once I would purposely bend over and flash to everyone my hot pink panties as a tease. I'm very certain every one of them was dying to suck my cock and would love to put their porker up my pooper. The host's wife, Jill, took an interest in me and wanted to help me with my makeup. Her husband Dani (Dan) was very nice as well and was not burly like some of the others. For the next meeting I could attend she said she would do my make up for me and show me all the right tips.

That next meeting was so exciting for me. I just came in sweats with a wonderful outfit to unveil after Jill did my make up. She was very diligent, and Dani watched and made coy comments. My desire was for her to make me look as sexy and sultry as possible and boy did, she ever! Dark eyes with lavender pink eye shadow, false eyelashes and blush pink lipstick and shimmering lip gloss. They let me change in private and my outfit was out of this world - beige, thick weave skintight wool pants that accentuated my cute boyish bottom, a lavender cowl neck sleeveless satin blouse, lavender demi bra, pink satin string bikini panties, white pointed toe 5" patent leather pumps plus a platinum page boy wig with matching silver and turquoise earrings and neckless, silver bangle bracelets.... WOW! I looked so hot and felt so gay that I had such a big hard on which might be a problem with the pants I was wearing. Quietly I pulled out my penis and wanked off into the sink. Whew! Much better!

If there was sexual tension at the previous meeting it was twice as much as this, as again, I was the center of attention with everyone flattering me how good I looked and I was soaking it all up. Jill and Mary Beth, whose husband was also a crossdresser, cornered me with many questions - does my wife know? She doesn't? Wow! How does this make me feel? Am I gay? All I could say was how can a man be dressed like this, talk softly and feminine like a woman and not feel sexually alive and yes feel more than a little gay.

I told them after a few glasses of wine how any real man would go gaga over me and how sweet it would be to suck his cock, to which they giggled. We'd love to watch you do it, they told me. In this steamy conversation, I told them its everything I can do to not take off my pants and blouse and prance around here in high heels, panties and a bra like a little sissy and show off for everyone. I was sporting a huge hard on that I saw the gals unmistakably look at. It was then getting time to leave, to go home to my drab life as a man. I went to change in the upstairs bedroom admiring myself as I undressed. There in the cute lavender demi-bra and panties I was so worked up I put my heels back on and pranced around the room, mincing about like the little sissy fag I had become. Just had to wank off again to relieve the sexual tension. Then, like Cinderella I had to be home and back to drab guy mode.

It was about 4 months later before I was able to attend another meeting and this time I was going to make it count - wifey was out of town. Bubble bath and shaved all over & under (I am naturally very light haired on my body anyway) then powdered and perfumed to get ready. I had contacted Jill & Dani to see if she'd do my make up again and told her that I had a surprise. She said come over real early, that she might surprise me too. Jill wanted me and Dani to wear our heels, stockings & panties as she did our make-up. I have to say it was smoldering as she did both our foundations, then eyes, then accents, then lips. Pleased with her work she had us put our wigs on and stand up. OMG, she had us looking so hot and femme. Needless to say, Dani and I both were sporting huge wood in our panties.

"Looks like you girls are a little excited" she quipped.

I had brought a number of panties to wear and for makeup session I was wearing pink stretch lace boy shorts. The outline of my aching erection was unmistakable in the dainty boy short panties. Dani had on flowered string bikinis; our cocks were so hard. Thinking that Jill really liked feminizing guys, and she did an excellent job feminizing the two of us. Jill was wearing simple khaki shorts and a faded denim button down shirt.

All through the make-up session her shirt was perhaps undone one or two buttons more than you would have expected, giving us tantalizing glimpses of her bra on many occasions. In one casual move she unbuttoned her shorts and let them fall to the floor. Stepping out of them, she undid her shirt, revealing herself in simple pink cotton panties and a light blue demi bra. Her titties were small but firm and Dani and I were in a state of shock at what just happened. Casually, she stroked each of us through our panties making us shiver in excitement, it was just so hot. Our cocks quivered.

"Our little secret" she said. "Nobody has to know".

Jill continued to fondle our penises through our panties, we were oh so hard. In one sly movement she stopped, un-snapped her lovely bra in front, pulled it off & tossed it aside. Her breasts were beautiful - for a woman in her early forties they were so beautiful - small and firm with small pointy nipples.

"You can look, but you can't touch" she teased us as we gawked at her lovely little titties.

With that she reached into our panties; the feminine touch of her hand on the flesh of my penis was arousing beyond belief and Dani looked at me in amazement at what had transpired. Our faces were inches from each other, we were leaning towards the other with longing.

"If you kiss it will mess your lipstick" Jill interjected. "I know you want to, but it will mess your pretty lipstick".