tagTranssexuals & CrossdressersHigh Heels and Stockings Tryout Ch. 03

High Heels and Stockings Tryout Ch. 03


My night of CD sex with Samantha and James had been so hot, it was practically all I could think about the next week. My wife and I had fantastic sex, with plenty of backdoor fun, including my wife sliding a lubed finger up my tight ass while sucking me, until I flooded her mouth. I also had her dress like a slut and slowly drove my cock into her bottom, pounding her the same way I'd pumped James' (Janet's) virgin ass the week before.

We fucked so often that she didn't go over to her best friend's house, with whom I was certain she have having a pussy-licking affair with. It didn't bother me that she was fooling around with her friend, since it wasn't like she was going to run off to Massachusetts and get married, so I let her have her fun and figured I'd work on a way to join in at some point.

More immediate was my desire to get back with Sam and James, and have more dress-up fun. My wife was going out of town the following week on business, and it was a great opportunity to see them again. I gave them a call, and talked to Samantha about the plan. We agreed I'd come over after work on Monday, and for me to bring over my slut clothes.

I drove my wife to the airport Monday morning, sending her on her way, and spend the rest of the day at work trying not to look at the clock and count down the hours until my date. At 5, I slid down the brontosaurs like Fred Flintstone, went home for a shower and to grab my slut clothes. 20 minutes later I was at their place.

Sam had told me to come hungry for dinner, and we'd be served by her maid, Janet, which was James' dress up name. Sam met me at the door, and looked super hot in her black high heels, tight business suit, and tasteful jewelry. She smiled at me and welcomed me in. "You look great," she said. "C'mon in. I just got home too, but Janet's been here awhile, getting herself ready. She can take your bag."

I then heard the click of high heels on the tile floor, and the CD slut of my dreams came walking in. Janet was dressed in the same French maid's uniform she wore last time - black pump heels, fishnet stockings held up by garter straps, exposed via an obscenely short skirt, tight top with a stuffed bra, beautiful makeup, and a cute white maid's ribbon on her head. But there was something even sexier about her since last time. She was so nervous then, her first time dressing up with someone besides her wife. But she was such a good girl that night, sucking cock to a creamy finish and using her tight, virgin ass to caress a wet load of sperm into her body, and the memory of that night gave her the confidence to be the sexy, alluring woman she wanted to be. She sashayed into the entryway with us, making love to me with her eyes and smile, and said "May Janet take your bag, Sir?"

"Please," I replied, my cock stiffening into the pink satin panties I had on under my slacks.

Janet walked between me and my bag, and in a move totally unapproved by hotels everywhere, kept her legs straight as she bent over at the waist to pick up the handle of my bag. Her short skirt rode up as she slowly leaned over, exposing her black satin panties, stretched tightly over her smooth bubble butt, her garter straps pressing into her soft skin and perfectly framing the bottom that had given me so much pleasure the time before.

She leaned back up, and straightened her skirt with her free hand. With a smile and wink, she walked down the hall.

"We're so glad you're here," Samantha beamed to me. "Janet's hasn't been able to stop talking about you since we made plans." I really did like this couple. Not only were they sexy and kinky, but truly nice.

"Janet would like to be our maid for dinner too." Sam then led me to the dinning room, and we sat down.

Janet served us dinner as swiftly and efficiently as the best waitress anywhere. I rewarded her with caresses on her thighs and bottom every time she came by the table, while Sam and I chatted. Finally, the meal was cleared off the table, and we retired to the living room for hot tea, poured from the pot by a leaned-over Janet. She then stood there, smiling at us, while we paid complements to how sexy she looked.

I told her how much I'd enjoyed taking her tight rear, and I'd fantasized it was her riding my cock when I was fucking my wife.

"Oh, she's been a such a hellcat in bed too. She's insisted I fuck her now christened ass with my strap-on ever time we're gone at it. I told you she was going to be a total slut. I'm just glad I've been able to keep her out of the men's locker room and off her knees since then."

Our sex talk excited Janet, and I could see a flush in her checks as we discussed how well she'd taken to sucking cock. I noticed a fullness to the front of her skirt, and pictured her sweet 6 inch cock rubbing against those black satin panties as she became swollen and hard.

"Yet," Samantha said, "she's still a novice cock sucker, and can use more training. Now watch Sweetie as I take care of this stud."

Sam dropped to her hands and knees in front of me, on the soft Persian rug, and crawled between my legs, slowly running her pink tongue across her wide lips. Tenderly and with her painted nails, she undid the button on my slacks, and zipped me down, exposing my pink panties, now wet with pre-cum.

"Sexy panties baby. I just love panties on a man, under his work clothes. Now Janet, watch what I do, and you'll get your chance too."

Sam peeled the tight panties away from my cock until it sprang out and brushed against her lips, wetting them with pre-cum from the leaking tip. I could feel the warmth of her breath on my cock head, and she opened up her mouth and slid my cock past her lips.

I groaned as the pleasure from her mouth hit me, then took my shirt off so Janet could see my chest heave and sweat as her wife sucked me off.

Tenderly, I ran my fingers through Sam's soft blonde hair as she found her rhythm, and bobbed her head up and down on my shaft.

Janet looked at her sexy wife, on her knees, skirted ass raised high in the air, lips sliding on my hard shaft, with a mixture of lust and jealously. Jealous of not herself being the slut on her knees before a swollen cock. Still, she was well trained, and didn't move or try to pleasure herself. After a few minutes of sucking, Sam popped off my cock head with a slurp, and told Janet to prepare the bedroom while we got ready.

She led me into their bathroom, where Janet had left my bag. Sam told me how much she wanted to dress me up again, and I stripped and sat on her dressing stool, pink panties only covering half of my stiff cock.

She took out my slut clothes, slowing sliding the fishnets up my legs, added the garter belt, and attached the straps, kissing the tender skin on the back of my thighs as she snapped the strap against me. I just love the way garter straps press against my bottom, creating the same frame as I'd admired on Janet. Next she put my bra on, stuffing it with extra stockings to make it full, and guided me into my cute schoolgirl top, with a little red tie. Then came my short plaid skirt, doing an admirable job of putting my leaking 7 inch prick out of view, though there was no way to hide such a thick cock.

Finally, my favorite part of dressing up - sliding into my 3-1/2 inch ankle-strap heels. Wearing high heels completes the transformation from a conventional guy into a slutty, cock lusting whore.

"Now Sweetie," Sam said. "I'll fix up your face, and we'll be ready for the fun to really start."

As before, Sam expertly applied blush, eyeliner, lipstick, and sweet smelling perfume, all the while telling me how beautiful and sexy I looked.

When she was done, she had me slowly stand up in my heels and turn around to look at myself in the mirror. I almost swooned.

Just like with Janet, the confidence I'd gained from last time relaxed me, and somehow made me look sexier and more desirable.

Sam took my hand, and let me to the bedroom where Janet had soft music playing, and scented candles burning to created a romantic setting.

"Doesn't Jenny look great," said Samantha, using my dress up name for the first time that night. "Now I've had a taste of her cock this evening. Janet, why don't you reacquaint yourself to her body too."

Janet and I moved towards each other, and like lipstick lesbians, our sexy bodies embraced as we wrapped our hands and arms around each other, slowly and tenderly pressing our lips into a kiss.

Her body felt like heaven. Sweet, feminine, and tender. I hope mine did too, and I think by her reaction she was as turned on as I was. We began to sway to the soft music, lost in the fantasy of being sexy women, dressed like sluts, but beautiful and feminine and needing a soft touch too. I began to trace hot and wet kisses on her neck, moving around her body to her back, and wrapped my arms around her. My cock was now rock hard, and pressed against her soft ass as she rubbed against me.

"Now Jenny. Before you get carried away with your cock, Janet and I had a talk, and thought that since you let her be a woman last time, that she could repay the favor this time. Would you like that Baby? Would you like to make Janet's cock come with you mouth and bottom?"

Of fuck yes, I thought. It would be the culmination of all my times cross-dressing. To finally take a swollen cock deep inside me, work it with all I had, and cause it to spurt its warm and sweet cum.

I nodded my head yes as it spun around the room, knowing that soon I'd have Janet's cum running past my lips. Janet guided me down to my knees, and moved her body in close to mine.

"Now you two sluts stay right there. I know it's going to be hard, but I need to change too," ordered Sam. She opened a drawer to grab some lingerie, and headed towards the bathroom.

It was hard. Hard not to lick my way up those stockinged legs to find my treat in her panties. But Janet and I passed the time looking deeply into each other's eyes, smiling and being so happy to have each other, while I gently caressed her calves and ankles.

Sam must have only been gone a few minutes, and as she came out of the bathroom, I thought to myself what good things had I done to deserve this. The time before Sam had just had on a simple but sexy baby doll. But this time she'd gone all out. High, open heels, sheer stockings with a seam up the back, a garter belt, and a beautiful ribbed corset top which swelled and jutted out her big and full breasts. Topping it off was a pair of turquoise blue panties, the gusset of them darker and soaking wet.

"All right Jenny. You did so very well. I love a good, obedient slut. Now you may continue on with servicing my Bitch. You'll find Janet comes like a porn star when she's dressed up and in heels."

I began my trip into full womanhood with a lick up Janet's legs, savoring the way her fishnets felt on my tongue, and the warm body below them. When I reached the exposed skin on her thighs I heard her let out a soft moan, as I tenderly kissed and massaged her with my mouth. Janet ran her fingers and painted red nails through my hair to guide my head where she wanted it, and led me to the front of her skirt.

She was so swollen, she pressed against her maid's costume and made a large mound. I kissed along the length of it, feeling its hardness though the soft material of her skirt. My hands slid along the back of her thighs to find and grab hold of her pantied ass, pulling her into me. Janet helped me out, and lifted her skirt above her panties. With trembling hands I traced my fingers along the top of her panties, from the back, until they were on either side of her trapped meat. I rolled them down, and her sweet cock, which had been bent to one side in her satin, sprang out and touched my face. Without thinking, just acting on instinct and desire, I opened my mouth and took her inside me. Now I'm a slut, and love sucking cock. But I think any man who'd been there on his knees before such a beautiful dressed up woman would have done the same. No man could have resisted the stiffness, thickness, and softness of the cock of a beautiful French maid brushing against his cheeks.

As I'd found out from before, cock sucking came so naturally to me. To Janet, probably to any man. We know what feels good, and how to pleasure a cock. I opened wide, and let her cock head rest against the flat of my tongue, Then slowly bobbed my head down on her swollen shaft, feeling her meat run along my tongue and lips till my mouth was full of this French maid's cock. Janet groaned as the pre-cum began to flow out of her cock, and I knew I was leaking as well. I moved my head up and down on her cock, feeling it thicken and grow in my mouth, throbbing with each beat of her heart.

I felt Sam kneel down beside me, and she put her face next to mine, obviously wanting a taste of Janet's cock too. I pulled off, and holding her cock in my hand, guided her into her wife's loving mouth. Sam only gave her a few sucks, then pulled the head out so both of us could lash our tongues over the sensitive and swollen head.

"Oh yes Baby, that feels so good," Janet let out. "You two look so fucking hot lapping your tongues together."

"Now Janet, you know what we talked about. Jenny gets your cum tonight. Christen her lovely face." With that, Jenny took a bottle of slippery lube and poured a bit onto my free hand.

"Lube her ass up. She just loves being finger fucked while she's getting a blowjob." With one hand still wrapped around her cock, I rubbed the lubed fingers of my other around her balls, feeling the pleasure surge through her body and cock as I massaged and stroked her sensitive cum pools. Then, I moved my fingers back to that special area between her balls and ass, rubbing and stroking her until gasps escaped her lips. Finally, back to her tight backdoor, no longer a virgin to cock, but still tight, hot, and butter soft. My mouth bobbed back and forth on her cock as I found her opening, and wet it with lube from my fingers, tracing circles around to relax and loosen her up. When I felt her lean back on her heels I knew she'd relaxed enough to let me in, and my insistent index finger slowly slide up her ass.

Her gasps gave way to moans as I penetrated her tight ass. While my finger was much thinner that either my cock, or Sam's strap-on, it was still a fanatic thrill for Janet, having her ass pleasured while fucking my CD mouth. I slid in as far and I could, and started to make this beautiful woman cum.

I fucked her most sensitive areas simultaneously. Her ass with my wet finger, rubbing in and out to stimulate her inside. And her cock, sliding past my tight lips with each bob of my head, met by thrusts from her tips. We moved together, a joined couple, fingers and mouth pleasuring ass and cock. Janet's hands held my head as she drove her cock into my mouth, as her asshole tightened and then clamped down on my finger.

Sam was watching from a chair, finger fucking her sopping wet pussy, as she watched her bitch approach her cum. How proud she must have been to help dress and train such a sexy woman, who was now going to wet another whore's mouth.

She groaned out obscenities as she watched us fuck, saying "Yeah, fuck that whore's mouth. Fuck it just like you like to be fucked yourself. You're going to pump that slut's mouth full of your cum. You're going to mess her pretty little face up. So fuck her. Fuck that mouth! God, you two filthy bitches look so hot."

Pre-cum began to stream out of Janet's cock and she approached her climax. Her moans of pleasure filled my ears and intoxicated me with joy, knowing I was going to bring this beautiful woman's cock to a sticky cum with my mouth. Janet picked up the pace, really slamming her cock into my mouth, until I felt her go completely rigid. It was like sucking an iron bar, she was so hard.

"Ohh yes. God yes Jenny. Gonna cum in your pretty mouth. Fuck oh fuck oh fuck!!!" she cried out as her orgasm hit her. The first blasts from her cock must have been pure pre-cum, as they tasted like liquid sugar. Groans escaped from her lips as more cum escaped from her cock, this time mixed in with slightly salty semen, filling my mouth with her rich and full taste. She must have been saving up for me, the slut, as she filled my mouth. I had to quickly swallow a load of her cum, just to allow enough room in my mouth for her dick.

Janet kept spurting, keeping my mouth full of cum as I swallowed again and again, loving the sweet and creamy taste of her cum, and in what it meant to me. I'd become a woman, a beautiful, sexy, slutty woman who'd made a cock spill its load using my mouth, and into my body.

She moaned like the cumming bitch she was, and pulled her still shooting cock out of my mouth. It landed heavily in her hand, and she pumped it, jacking off the last few spurts of warm cum over my face. It felt warm and thick running down my cheeks and lips.

I couldn't keep my mouth off her cock, so I pushed her hand away to have her in my mouth again. It was so fucking hot to have a warm, soft skinned but still stiff cock in my mouth as I swallowed around it, my monitions massaging her cock and I sent her semen down my throat and into my body.

Janet relaxed against my body, running her fingers through my hair, saying "Oh Jenny, you're so good. Fuck I came so hard."

"So did I." I heard a voice say. In my lust of making Janet cum I'd lost track of Sam. Now she too was standing in front of me. I adjusted my eyes to focus on her and saw a thick, pink cock sticking out obscenely from her crotch. She'd put on a strap-on, and was offering it for me to suck. Greedy for new cock, I let Janet out of my mouth and into my hand, and wrapped my cum wet and slutty lips around Sam's. Her cock was beautiful too. Pink, thick, and nicely shaped. It couldn't compete with Janet's real fuck stick, but knowing it was attached to a totally slut of a beautiful girl made it hot and sexy too. Sam pulled out to smear the cum all over her cock, and then began to fuck my mouth too.

"Suck my cock you whore!!" she commanded, really drilling her cock into me. She was far more assertive and demanding than I'd seen her before, and I loved knowing I'd turned her on so much that she needed to step out of her normal mode to give a good fucking to someone. With hard thrusts she took my mouth for her own pleasure, the strap-on harness rubbing against her clit to help her get off, if the nastiness of fucking a CD with cum all over her face wasn't enough to make her climax by itself.

She pulled out and told Janet "Get you cock in her mouth too. We're both going to fuck this bitch, so let's get started." My ass quivered at the sound of that.

I opened wide, sticking my tongue out like a good little whore, and they stuck as much of their cocks in my mouth as they could. I felt used, stretched, and totally complete.

"On all four's, whore," she commanded me. "We're going to get our use out of you. Janet, get her ass ready for a good fucking." As pulled my mouth away from their lipstick stained cocks, I dropped down on hands and knees, and pulled my skirt up over my ass. My own cock was so rock hard and throbing I knew I'd blow my load if I touched it, so I kept it wrapped in my soft panties as I felt Janet crawl between my legs.

"Get this slut good and wet. Remember she's a virgin, so she'll need lots of lube." Janet's breath warmed my ass as she traced kisses over the soft skin, working her way down to my asshole. Then, Heaven.

Janet's wet tongue began to flick and lick my tight, virgin to cock, ass. She licked all around my hole, then darted the tip inside while my moans filled the room. If I'd be allowed to have my hand on my cock, I'd had spurted cum everywhere, but I knew Sam wound not have allowed it. So like a good little Bitch I just rotated my ass around Janet's mouth, and waited for my fucking.

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byneon_noodle© 17 comments/ 180164 views/ 34 favorites

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