High Heels and Stockings Tryout Ch. 03

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Soon cool lube was smeared over my aching backdoor, as Janet loving got me ready to take my cherry.

"Back on the cock bitch. It'll give you something to do while Janet gets you wet and slick." Sam pushed her strap-on past my lips again, and settled into a nice, slow reaming of my mouth, as Janet slowly pushed a finger inside my ass.

I'd had Sam's finger up me from last time, but this was the first time I'd had Janet deep inside me. God, it felt so good to accept part of another person's body into mine. I started to understand the feminine side of sex. The feeling of taking your lover's body, accepting lovingly what they have to pleasure you with, and surrounding them with yourself. Janet's finger was coating my ass inside and out with slick lube, so the first entry of a cock into my ass would be as it should be - slow, easy, and pleasurable.

"She's wet enough now. Janet, will you please break Jenny's cherry? Would you like her to do that Baby? Do you want my slut to claim your ass as her own? To fuck and pound and soak with her cum?" Sam pulled her cock out of my mouth to let me talk.

"Please Janet. Fuck me. Fuck my ass. I'm here for you. I'm your slut. Mount me," I moaned.

Janet drew herself closer to me, pressing her stocking-clad legs against mine. Pressing her slutty heels against mine. Pressing her pushed up skirt against mine. With one hand she gently pushed my bottom apart, and with the other guided the head of her cock against my tight, but slick, wet, and horny asshole.

We kissed with our bodies. The same way I'd taken her ass from last time. As intimate a touch as two males could be. Cock and ass. Each having what the other needed. I needed her meat. Thick and hot inside me. Filling me. Fucking me. Making me feel like a woman. Like a slutty woman who loved being treaded like a whore and fucked. Janet need my soft, sugary walls wrapped around her prick. Squeezing her. Massaging her. Pulling the cum from her cock. Giving her a garter belt wrapped waist to grab, and hold, while she fucked a slut with her cock, driving it in and out. Taking me, dominating me, using me for her pleasure.

Janet pushed forward, and I pushed back, and her beautiful cock head began its entrance into my ass. I was tight, but wet and relaxed, and a slut for cock. So her head soon passed my outer hole, as I opened up around her shaft.

The biggest groan of my life passed my lip-sticked lips as she entered my ass. "Ohh fuck yes. Fuck your slut. Fuck your slut!!" I managed to get out as she buried herself inside me. Gently and slowly she filed my backdoor with her cock, letting me get used to the size and shape of it, as my ass stretched around her.

Sam was jerking her strap-on like a real dick, inches away from my face, quietly, and consumed with lust as she watched her bitch take a slut's anal cherry.

It was like each inch of her cock going into me made me feel more and more like a woman, filled with another person's body, until her warm balls touched mine. We were joined as lovers.

It was an unbelievable riot of sensations. Dressed like a schoolgirl slut. My stockings and heels gripping and caressing my legs and feet. And that beautiful cock, which I'd just sucked to a wet climax, sheathed into my ass. We stayed in that position for a few moments. Savoring the intimacy, the touch, the heat. My cherry had been taken by this beautiful CD French maid, and I was so happy to give it to her.

Then we began to fuck. Slowly and softly at first. Janet pulled a bit out of my ass, and then thrust into me. Each stroke became a bit longer, the thrust harder, as she held onto my waist and garter belt, getting a good hold on her ass whore.

The intense, overwhelming pleasure of our intimate embrace had subsided by now, leaving us above to control our bodies again, and allow lust to guide our actions. So we thrust at each other. Janet fucking my ass, spurring me with her cock, while I bucked back on my new lover's dick, loving being her slut.

"Janet, Janet baby. You cock fills me so good. I'm so fucking full. Ohh yes. Pump your whore. Pump your slut. Take my ass!" I spurred her on with my nasty sex talk. Sam must have thought I'd recovered enough by now, and pressed her cock to my lips, which I gladly opened and began to suck on. Now I was totally theirs. Split roasted by this gorgeous couple. Filled at both ends, each using my hole for their own pleasure, and knowing their double fuck was giving me the time of my life.

Sam grabbed hold of the sides of my head so that she could better ram my mouth, as Janet's, kept pumping my ass. I was in pure sex heaven. My own cock was bobbing against the schoolgirl skirt, rubbing in circles against the soft material. Oh I needed to cum so bad. But without a hand or mouth or ass directly touching me, I was sentenced to being Sam and Janet's fuck toy until they were satisfied.

Soon though, the tightness of my ass was going to be too much for Janet. I felt her cock throb, sending drops of pre-cum into my body. Sam could see Janet reaching her cum, watching her face go dull with lust and pleasure as her body built towards her climax.

"Fuck your whore you bitch!!" Sam yelled out, filling my mouth with her cock as my saliva dripped out around the shaft and dripped down onto the rig. "Cum in this whore's ass. She wants your cum blasting into that tight hole. Fuck her. Fuck that asshole. Make your cum drip out of her ass!!"

A final squeeze of my ass was all it took. Janet groaned in total pleasure as her climax hit her. Once again, her cock went rigid inside me. It felt like it was splitting me apart as she swelled. Then her cum began its trip from her balls to my asshole.

"Cumming, cumming you slut. Take that wet cum!! Ohh fuck, Ohh fuck!!" was all she got out become it just became a long moan. Woman say they usually can't feel a cock cum inside them. Maybe asses are more sensitive. I felt Janet's cock shake as the cum shot out, and felt it spasm as the globs of wet juice spattered against my ass walls. Oh it felt so good. Better than anything I'd ever felt before. To cause the total pleasure of someone you cared about. To take them inside your body, and make them give up a part of them, their wet, life giving sperm. I felt like a woman, and loved it so.

Each blast of cum wet my tight tunnel, until Janet's cock was slick with cum. It moved so easily inside my now taken, fucked, and cum soaked ass.

"Please touch my cock. Make me cum. Please!!" I begged. I need just a touch, a squeeze, a caress to blow my own load. Sam took pity on my pleas, and while Janet kept fucking and pumping cum into my ass, she pulled out of my mouth to lie on the floor under me. Her manicured nails and fingers wrapped around my cock, her mouth directly under my cockhead, mouth wide open.

"Give me your load whore!" she ordered, and I obeyed. It was the best climax of my life. With Janet's cock still pumping my ass I felt so full, so used, so fucked, and it was if her cockhead pushed my cum out of my balls.

The first blissful spurt was pre-cum, as it flew out before my orgasm hit. It hit heavily against Sam's face, then the rest of my cum followed. I blew rope after rope of sticky, hot cum, as I lost control of my balls. It was all I could do to keep myself upright on my hands and knees as the cum kept shooting out of my cock, completely soaking Sam's beautiful mouth, lips and face. After what seemed like 30 seconds my spasms ended, and I still dripping my spunk out of the tip of my wet cock.

Janet slumped against my ass, resting we came down from our cums. Sam released my cock, saying "Fuck Jenny. I can't believe how much you came. Look at me."

She moved from under me and got on her knees as I focused on her face, now painted with my white and sticky cum. It dripped in streams off her chin and began to drip down onto her heaving tits.

"Great job lover. Now Jenny, clean me up." Sam shuffled over to Jenny and must have offered her cum drenched face to her bitch, as I heard moans from Janet, and wet sucking noises as she cleaned her mistress up, her cock still slowly and rhythmically pumping my ass.

Their tongues danced in each other's mouth as they Frenched and licked up my jism. Finally, Janet slowly pulled back, and the head of her cock popped out of my asshole, causing a gasp from both of us as our intimacy was broken. I felt cool air touch my most sensitive part as the warmth of Janet's cum began to drip out of my ass, its touch caressing my stretched hole like soothing lotion. No longer able to exert any strength, I collapsed onto the rug as I basked in the glow of my deflowering.

Sam and Janet jointed me on the rug, three pairs of stocking and panties touching as we embraced, exhausted but ecstatic. I'd jointed them in being fucked like a woman, and it was so wonderful.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
23 Comments
drobert44drobert44over 1 year ago

So sexy, the CD's.........

AnonymousAnonymousover 2 years ago

Wow!! Wish I could give it 10 stars! I am married but after learning to love cock at an early age, embraced closeted bi sex as my "label" of how I enjoyed sex. The loss of my wifes sex drive to illness, and way too many "go gay for fill in the blank here" videos, crossdresser orgy videos and then sissy slut trainers, I'm afraid the needle has moved all the way to gay! I actually hardly ever jerk off to, or, get turned on by straight or bi sex porn, but this story was HOT HOT HOT! My wife went shopping this morning and, as soon as she left, it was into crotchless tan pantyhose, 4", strappy gold heels, a black satin baby doll with triangle holes for my plump titties and my slutty black curly wig. Lubed up and worked my asspussy open enough for the real skin 8" vibrating cock, and began stroking while reading. What. An. Orgasm. More, more, more, please!

AnonymousAnonymousabout 3 years ago
Stockings

I am a full on sissy cross dresser love to suck dick and get fucked.My new friend comes over and in joys having sex with me weekly.He has such a nice dick i have been known to milk him dry.Just the other day he brought a friend with him for a threesome.I have not had a black dick in my mouth or ass in some time.They both took turns fucking me and i sucked and milked both dry.

AnonymousAnonymousover 3 years ago
Wonderful

Thanks so much for this, l have just filled my high heels with cum reading it!

Riki1942Riki1942about 4 years ago
What Comes Natural

I know what you mean about sucking cock and getting fucked! Once it's in your mouth or ass, there isn't much to figure out. Your body knows what it needs and it just takes over and does what comes natural.

My boyfriend and I are both divorced, have never been with a woman and a man at the same time and are no longer interested in the opposite sex. He wears pantyhoes sometimes and likes getting fucked now and then but, I'm the crossdresser in the relationship, the one that sucks cock and, usually, the one that gets fucked.

I love all the nasty talk in your story and it really turns me on when he says those thing to me when we are having sex. I really AM a cum slut! We bareback and I love to swallow and I take his load up my butt when we fuck. I don't want to be a real woman but, when he calls me a Whore and tells me he is going to knock me up and make a baby in me as he cums, I almost wish that he actually could get me pregnant! It makes me feel soooo kinky!

Riki

Show More
Share this Story

Similar Stories

Wife's Idea Wife teaches Hubby new tricks.in Group Sex
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
More Stories