My doorbell rang. My boyfriend was supposed to be picking me up, so who was this statuesque blonde on my doorstep? She was dressed in a tight little black dress, stockings and stilettos. Quite beautiful. “Hello, Toby,” she said. OMG, it was my boyfriend, dressed in drag!
I stepped into him and gave him a big kiss, wrapping my arms around his neck. “You look so hot, babe!”
I ran my hands over his body, across his ass, around his hips to his cock, which was getting hard under his dress.
“Come in. We don’t want the neighbors seeing what’s going to happen next,” I said, pulling him inside.
I was wearing a little red dress, and he pushed it up over my hips and pulled my panties down. He got down to his knees and started kissing and licking my tummy, my thighs, my sex. He picked my left leg up and slid it over his shoulder, dug his fingers into my ass and pulled my pussy into his mouth. He pulled the hood on my clit back and sucked. My legs started shaking as my orgasm started to build, and then I was cumming in his mouth. I dropped to my knees and kissed him, tasting myself on his tongue. My hand went to his cock again… he was harder than I’d ever felt him. I pulled his dress up over his head. He was wearing a black bra and matching panties and had a black garter holding his stockings up. I took his big cock into my mouth and sucked as I slid my hands over his body, under his bra, pinching his nipples.
He pushed me off his dick, stood up and pulled me to my feet. Bending me over the couch, he slammed his cock into my wet pussy and began fucking me. Every thrust was harder than the last and I started cumming again. He pulled his cock out of my pussy and then I felt his fingers…. he began lubing up my tight little ass hole with my cum, and then he pushed his cock into my rosebud. His fingers went to my clit rubbing little circles as he worked his way into my tight little hole. Pumping his hard cock in and out of my ass and playing with my pussy, I felt my climax building yet again.
“I’m going to cum again for you, babe… cum with me…” I moaned as we exploded together.
Archive for the 'Crossdressing Phone Sex' Category
Page 13 of 24
Whatever path we go down. I know you will be squealing with pleasure.
~Princess Paris~
I have the coolest new boyfriend! He said he had a big surprise for me for Mardi Gras. He is a little shy so I wondered what it could possibly be since I figured we would be staying in. I set up my roof top porch with some munchies and a bottle of bubbly. I lit some candles and now it was time to get myself ready.
He really loves lingerie so I decided to wear my sexiest corset, matching stockings and panties and stilettos. I was all ready and there was a knock at my door. He is never early, but I always excited to see him. I opened the door and it was a very tall women kind of dressed like me. She was blonde and her make-up was perfect. She was stunning. As I stood at the door confused he said ” Amanda aren’t you going to let me in”. OMFG, it was Corey.
He hugged me tight and I could feel his cock hard against his cute little black mini skirt. We went out to the porch and sat down and ate some munchies and drank some bubbly. His kisses tasted go good with the mixture. People were walking by below us and watching us kiss. Who wouldn’t want to watch two sexy bitches kissing. Then Corey had an idea.
We went to my dressing room. I do costume work so I always have spur of the moment clothes on hand. He wanted me to dress like a man. Corey is 100 percent guy but his kink is dressing like a woman he explained to me. He loves the feel against his skin. He pulled a grey old fashioned tux from my closet. I tried it on over my corset and panties and it fit pretty good. I put on a black pair of flats and put my long red hair in a bun. We stood together looking in the mirror I was giggling till he started to kiss my neck and push his cock against me.
Corey and I went back out to the porch. Wanting to attract more attention we started tossing down beads. We kissed more with our bodies pressed together tight. There was maybe 20 people below watching us. I sat down on the chair and Corey unzipped my pants. He got on his stockinged knees and started lick my soaking wet pussy, I loved having a crowd watching us. After I came all over his face, seeing the smeared make-up made me even hotter. I wanted him to fuck me so bad. From below you really could not tell I was the woman and him the man. He pushed his silky panties to the side and slide his cock into me. It looked like a woman was riding a man. The crowd below was cheering us on as he fucked me harder and harder. Then he did something I will never forget ever! He pulled out of me and with a few more strokes shot his huge load of creamy sticky cum out to the crowd below. I wonder if next date I can talk him into going out in public to a dark bar with us both cross dressed.
I love dressing up my sissy boy and parading him around for my friends to see. Let’s play some cross-dressing games! I’ll invite a few friends over and we’ll have a lingerie fashion show and you can be the model. I’ll start you off in a pair of sexy, slutty thong panties with a pretty little baby doll top. I’ll add a garter belt and a pair of thigh highs with some strappy heels and then I’ll present you to the group of girls.
You’ll feel like a total whore as you wiggle your cute little panty boy bottom in front of my friends. I can only imagine your humiliation when you see that each of us is wearing a big black strap on dildo, just for you! We’ll make you get down on all fours and enjoy a night of cock sucking and butt fucking , doesn’t that sound like fun?
Leanne
THE FANTASY CONTINUES:
My Pretty Pantyboy Pet and I get invited backstage to the After Show Party with all the Victoria Secrets Models. We got invited after flashing the models our own sexy little lingerie during their runway walks.
Once we are backstage, the beautiful models are “oohing and ahhhing” over us. The models make us sit in a couple of chairs in front of big mirrors. Professionally trained make-up artists and hair stylist descend upon us. They make us look amazing!
We both get glamorous makeovers. After hair and make-up, we are dressed in Gorgeous Victoria Secret’s Lingerie. I am put in black and red. You are put in black and hot pink!
The famous photographers start snapping our pictures.
We are asked if we want to keep the lingerie. We admit that we are willing to do ANYTHING to get to keep the most beautiful lingerie in the world!
Isabelle
You and I get invited to the Victoria Secret’s Fashion Show. Special VIP Invitations!
We are both so excited that we can hardly contain our excitement. Our seats are right there in the front row.
What should we wear?
Let me help you pick out your sexy/slutty outfit! Let’s wear matching little black lacy bra and panty sets.
As the beautiful models walk past us on the runway, we flash them our little panties and bras. They are highly amused by our antics.
WE GET INVITED BACKSTAGE!
OMG!!!!
All that new Victoria Secret’s lingerie. I wonder what will happen backstage with all the models!
Join me in the ultimate Panty Boy Fantasy!
Isabelle
Naughty naughty panty boy. I was doing some cleaning this morning and guess what I found? A pair of my favorite Victoria Secret panties wadded up between the cushions of my couch filled with cum. I know it was you! It’s my turn now to have some fun with you since you like to thief my things. I went out and bought you a few pairs of your own sexy panties. I’ll tease and taunt you. That’s right you sexy little panty princess, get ready to be sissified. I know you secretly love to tuck your tiny little penis between your legs. Admit it! You love the feel of the material rubbing against your clitty. It makes you want to squirt your juices. Don’t worry about getting your new panties dirty. We can always shop on line for some new panties for my naughty sissy princess. When I’m finished playing with you, your panties will be filled with your warm cum and if your a good bitch then I’ll let you eat your cum right out of those sexy panties. Don’t try to deny that you don’t like the taste. Be a good bitch and clean them up now.
~ Princess Paris ~
I am going to a once a year Fetish ball. It is the one special thing I do for Anthony for being a very good servant to me. He is my maid, cook, and over all cleaning up my messes servant. He has been so loyal that it is my present to him. He has been with me since I left home at sixteen. He tried to molest me but poor pathetic little loser could not get his little pin dick hard for someone as old as me.
At the end of the night there is an auction to bid on a special little boy or girl to bring home with us. Anthony used to pretend he wanted a little girl but in the end it is a boy that makes a little puffiness in his pink panties. While strong to help me he looks pretty much like a woman at this point. A used crack whore kind of woman but most men can’t tell when he is sucking their cocks he is a man. I am in a latex gown and 8 inch stiletto boots. Anthony doesn’t need a wig any more as his hair is long. He is in full make up, in a little pink frilly dress and collared. I let him snort a line off my boot and rest is for me. He crawls out to the black limo that is waiting for us. He is to be on his knees the whole time. Till the auction he is to suck cock and get his ass fucked and fisted by all that please. I love to see him giggle like a little girl at all the big cock that is there. He is such a sissy slut cum dump. The night is going awesome and I am so fucking high. It is almost time for the auction.
Everyone has left except for the twisted, depraved pervs here for the child auction. I do another line and wait as the children are brought out and lined up. How degraded and confused they must feel. This is Anthony’s night so I hold my excitement and let him pick. He seems to have his depraved girly little black heart craving a blonde boy of about 6. He is adorable with a fragile little pale body. He is told to present his little dick to the buyers and Anthony just swoons. Things are taken care of the the little boy is bundled up and taken out to the limo. I give the boy something to knock him out till we get home.
Once in the house Anthony takes him to his room in the attic. He lays him down on his bed and comes down to thank me. I tell him what a sick, twisted pathetic excuse for a man he is. I spit on him and tell him the sight of him makes me want to vomit. He gets down on his knees, kisses my boots and retreats to the attic.
I dress you up in a black lace thong, fishnet thigh highs slither up your legs. I add a pink skirt and a laced up black corset top. Your long black hair grazes along your back. The smokey eye makeup is going to draw a lot of attention. I look into your green eyes and tell you it’s time for the finally touch, 5” stripper heels clear with chrome heels. It’s time for your task, picking up a guy at the bar. You enter the bar and see your pray. Go ahead, wrap your arms around him trail your hand to his cock. He is hard and huge. Tell him you want to fuck and take him to the dark hallway. I sneak around the corner and push him up against wall. I lean to you and whisper, “it’s time to take him for me.” Guide your head down to his dick. You know what to do. Suck his cock, taste his dick like a good whore. I love watching you suck him. Drain his balls for me. I want you to taste a real mans cum. Hold it in your mouth and kiss me. You have pleased me once again. Now, for the next task, bend over.
It’s a mixed up muddled
up shook up world except for Lola
lo lo lo lo Lola
Sometimes I love to go out in a Tux. Only to the finest clubs, of course. I wear black stiletto heels but wear the pants just long enough to cover them. A silk white blouse, my hair up and just enough make up to baffle. Baffle I do! My lover always has a blast watching me attract confused men and hot women.
We had a perfect table far back enough for some privacy and for people to wonder If I was a hot woman or a very pretty young man. There was a table next to us with 3 club girls. Young, hot and perfect fake round boobs. I asked one to dance the she took my hand as we got on to the dance floor. I pulled her tight pressing my boobs against hers. I cupped her tight ass and nibbled on her neck. My lover was in bliss as he watched us and stroked his cock under the table. We danced for 2 songs, making out on the dance floor. I slid my hand in her dress cupping her hard round tit in my hand, it felt so fucking good. When we finished dancing I led her to our table. The look on her face was priceless as I kissed my lover hard, sliding my tongue in his mouth. She sat between us as both our hands caressed her firm warm thighs. We had a three way kiss as my lover and I rubbed her pussy, feeling it get so hot and wet. I took my fingers to his mouth as he tasted her. Then he did the same for me. We fondled and fucked her pussy with our fingers till she squirted all wet and sticky all over our hands.
She and I went under the table, his cock was already out for us. We both licked up his hard shaft meeting at the mushroom head and teasing his pee hole as we kissed over it. His pre-cum is so delicious that I can’t get enough. I sucked his hard cum filled balls as she took his cock into her warm wet mouth. We both worked on him till he shot his load of cum in her mouth. There was so much it dripped out of the corners of her pretty mouth. I kissed her as we shared my lovers cum shot. Then we both sat back next to him as I told her she should ride him and cum hard while I watched. I sucked on one of her huge nipples and he sucked the other. She rode his cock fast till he came inside her shooting his second load of cum. I slipped my number into her hand and sent her dazed back to her friends.
We both zipped up our pants and he grabbed my hand and took me to the men’s room. There were people in the stalls but that made it even hotter. He slide off my pants and bent me over the sink. He got on his knees and started to lick then tongue fuck my round perfect ass. I started to moan loud as the 2 men walked out muttering something under their breath. Jim started to kiss the back of my neck, let down my blonde hair as he pushed his every so hard cock into my ass. He pounded and pumped me with his fingers in my pussy as we came again together with someone at the door watching us. We finished fucking and left the men’s room. I walked by her table, kissed her hard and we left. I hope she calls soon, as my strap-on is ready for some hot ass while my guy fucks her pussy. Oh yes!
Oh my Lola, la la la la Lola la la la Lola
