Put it on!

By anotherfeeling

Original link: https://www.lushstories.com/stories/crossdressing/put-it-on.aspx

Tags: First time, Housemate, Crossdresser, Anal

Added: 16 May 2011 Views: 44071 Avg Score: 4.86

A not-so-reluctant housemate dresses for his live-in landlord
I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and again but at least the sex sounded good, if the rather loud sighs, moans, groans and shrieking I could hear most nights through the thin bedroom walls were anything to go by.

Then one workday evening I came back to find Steve sitting on the sofa drinking a large whisky. "Manuela's left me," he blurted out. "Have a drink and sit down," he said.

I didn't really want to but I felt a bit sorry for him, so I poured myself one and sat down next to him. "She came round during the day and moved all her stuff out," he continued. "Well except this, it was under the bedcovers, she must have missed it," he laughed.

My attention was drawn to some unspecified black satin and lace garment next to him on the sofa. "Oh," I said, a bit nonplussed, thinking to myself that Steve must be quite drunk.

"It's an open-crotch teddy," he announced, holding it up right in front of my face so that I could see for myself.

Sure enough, there was a large gaping slit in the material of the crotch. At this distance I could even spot what were presumably splashes of her cunt juices around the edge of the slit. I couldn't really say much, I was taken aback not just by the teddy itself and the fact that he was showing it to me, but also by the signs of recent sexual activity and the fact that Manuela would even wear something as slutty as this. She didn't seem the type. You never know!

Then Steve dropped his bombshell. Leaning over and looking very intently into my eyes he ordered, "Put it on!"

"What?" I cried.

"Put it on!" He was serious, drunk but deadly serious.

"I - I can't," I stammered.

"Yes you can," he replied, "you will like it."

By now he had grabbed my arm, I felt frightened, so I said quietly "no" and slipping out of his grasp went quickly into my room, locking the door. There were a few knocks on the door, then silence.

The rest of the evening passed slowly, I was too scared to come out of my room. But yes, I was turned on. While I still lived with my mother I would secretly dress up in my sister's clothes, then later my mother's clothes herself. I was a classic crossdresser, the oldest son, a strong female figure was running the family, there was no male influence as my mother was a single parent. I thought I'd managed to give it up when I went to college, but now the old urges were back with a vengeance.

I lay in bed, playing with my raging hard-on, imagining how the sexy lace and satin would feel stretched over my shoulders, belly, hips, buttocks, how dirty I would feel with my erect penis sticking out of the open crotch and my tight virgin arsehole exposed too. If I'd tried it on maybe I'd have taken Manuela's place in Steve's bed, being fucked by him while wearing the same slutty costume she used to wear when he fucked her. Then another fantasy came to me, one I would even maybe put into practice.

The next morning I waited till Steve had gone to work before coming out of my room. The teddy was still there on the sofa, I picked it up and stroked the sexy material, lifted it to my nose and breathed in Manuela's pungent scent. The urge to try it on was overwhelming, but I somehow resisted.

I phoned in sick to work, got dressed and after waiting a bit of time for the shops to open went out shopping. And what a shopping trip - I had decided to embrace my crossdressing tendencies fully, and submit to the wanton desires that would bring, it was time to start building up a wardrobe. Nothing from a sex-shop though, I was shopping in Topshop, H&M, Miss Selfridges, Debenhams, even Harrods. Real shops selling real women's clothing full of real women buying it up. And me too.

The experience was liberating, by lunchtime I had bought a little black dress, a short flowery flared summer dress, a pink baby doll nightdress set, black lacy suspenders, bra and panties, a white basque and matching thong, a flowery bra and panty set, various sheer stockings, some with seams, some with lacy tops, fishnets, a black miniskirt, a pink and a white blouse, high heeled strappy silver sandals, black shiny slingbacks, makeup, perfume, jewellery, 2 wigs - one long and blond, one dark in a bobbed style, and a large tube of KY Jelly.

I got it all back home, then went out again and bought some food, before texting Steve to tell him I'd cook tonight. "That's good!" came his reply quickly, maybe he still felt embarrassed about last night.

So back home again and now it's time to get ready. First of all an anal douche using the shower, I feel very clean afterwards, it's a strange feeling sitting on the toilet peeing like a woman but it's water squirting out of your arsehole. Then a bath and shave all over. I'm not very hairy but even so the feeling of my smooth freshly shaved legs brushing together as I walk is incredible. My bare smooth cock, balls, mound and arsehole feel great too, it's all I can do to stop myself from wanking off. Then on with the makeup, and nail varnish for both fingers and toes. Some jewellery, perfume, then the black bobbed wig.

Now I'm ready to get dressed. I decide on the little black dress, white basque and thong, champagne lacy top stockings, and silver strappy sandals. As I fasten up the basque I watch my transformation into a sexy dressed-to-kill woman in the mirror. My cock is rock hard. I slide on the stockings and attach them to the suspenders of the basque. Then it's on with the thong, it feels good as it glides over the stockings, then nestles in the crack of my buttocks, the lacy front panel cradling my balls. My erect 7" cock sticks out the top. Then I slide into the little black dress, zipping up the back. The length is perfect, above knee but not so short that the stocking tops show at the front if I'm standing straight. A glimpse of stocking top is visible at the slit up the back, and sitting down, bending over or stretching up it becomes very clear that I'm wearing stockings and not tights. Then on with the sandals. I strut around in front of the mirror. I look great, sexy high heels, sexy short dress, sexy long legs. With the heels I'll probably be a couple of inches shorter than Steve, which is nice. I feel 100% woman.

I get the food ready, a bit of a rush but finally everything is finished 10 minutes before he normally comes back. Just one thing to do now, I go to the toilet, pull down my thong and squeeze what feels like half a tube of KY Jelly up my hole. It's wet, cold and slippery. I pull the thong back up. The slippery gel is oozing slowly out of me, as I walk my buttocks slide easily against one another, and I can feel my thong getting soaking wet. I am a woman, ready for a man.

But now the anxiety creeps in. What if he doesn't want me? The teddy is still on the sofa, I hope he really did want me to wear it for him. Then the door is opened, Steve walks in, and almost falls over when he sees me. "Oh my God! It's you! You look fantastic! I knew it! I knew you were that way inclined!"

With those words my inhibitions are swept away. I strut over towards him in my high heels, put my arms round his neck and kiss him slowly and deeply. He responds, sliding his tongue down my throat, cupping my buttocks and pressing me against him. I can feel his erect cock pressing against my belly, he can probably feel mine through my dress too. "Will we eat?" I ask.

"No way," he replies, and lifts me up and carries me to the sofa. I like that very much, he lowers me down then sits beside me. His hands are all over me, and I gradually remove all his clothing, until he sits naked beside me. I bend over and start to suck his beautiful thick cock. Before very long he shouts, "Stop, I want to fuck you, I can't hold out much longer!"

My skirt is pushed up, and I raise my buttocks let him pull off my thong. The feeling as the skimpy thong is pulled down my stocking clad legs is electric. My cock is exposed, he starts to suck it but I have to tell him to stop right away, I'm so close to coming. "Are you ready for this?" he asks.

"Yes, but-but I'm a virgin," I stammer, panting with excitement.

"Not for long," he says. He grabs my legs by the ankles and bends them right back to my shoulders. My wet slippery hole is completely exposed. I feel his big thick cock head press against it. He looks like he's got 8" with a good girth. It's sore, very sore but finally he manages to push his way in. As he starts to thrust backward and forward the pain is replaced with waves of pleasure. His strokes are long and slow to begin with, but even so the excitement and the pressure against my prostate is too much, I moan, sigh, gasp and finally shriek as I come in a blinding orgasm, squirting spunk all over my belly and the front of my little black dress. "Yes come you filthy little bitch!" he shouts as I shoot my load and he starts pounding me harder and harder.

"It's my turn now you slut!" he shouts as his cock slides quickly in and out of my slippery virgin hole. I love the dirty talk, he's calling me a whore, comparing me to Manuela, saying he's not sure who's the best fuck, we're both sluts but he's going to fuck me regularly until he can work out who's best! I get hard again, and another orgasm mounts as Steve's beautiful cock is pounded frantically in and out of my by now voracious tranny-cunt. "I'm coming you dirty bitch, you're getting my spunk!" he shouts.

"Yes yes," I cry, "fuck me, fuck my brains out, fill me up with your lovely spunk!" Then he comes with a massive groan, I can feel his cock twitching as he squirts his spunk deep inside me, and I come hard again, my legs still held tight in place by the ankles so that I shoot a second load of cream over my little black dress. Incredible! He pulls out of me exhausted, and I can feel his heavy load of white creamy goodness oozing out of my hole.

I'm too exhausted to do anything for the next 15 minutes, then I gradually wake myself up. I feel very proud of my performance, I was panting, shrieking, moaning and groaning involuntarily, just like a real woman, just like Manuela, and I came like her too, without touching myself and with Steve's big hard cock pounding away inside me. I want to be a better fuck than Manuela, I want to be a dirtier, filthier slut than she is and satisfy Steve completely. I strip off out of my dress, high heels, basque and stockings. "What are you doing?" Steve asks lazily.

"I'm putting it on," I say, reaching for Manuela's open crotch teddy.