Crossdressing In The Bedroom

Crossdressing in the Bedroom -- How it Started

(Even though I'm not, I have attempted to write this from the viewpoint of a man. I hope I've done this justice)

My favorite football team is whoever is playing the Dallas Cowboys that week. Sue was having some fun with me and wanted to make a bet that the Cowboys would win.

I was so sure I would win the bet that I didn't think to weigh the stakes. If I won, she would dress up to go out Saturday evening wearing a skirt that is above the knees, stockings, and no panties. But if she won, it was almost the same bet, I had to wear her stockings and no underwear, but at least I could wear them under my pants when we went out. So even if I lost, no big deal.

Then she tossed in "But you do know, if I win, you'll have to shave your legs... or actually, I get to shave your legs!"

This bet was starting to get a little one-sided. Still, I felt it was a sure thing so I took the bet. The bad thing about a bet like this is that there is no spread -- no margins. Well the Cowboys lost and Sue spent the whole week reminding me every chance she had.

Saturday after breakfast, Sue decided it was time to pay up "Come on, it's time to prep you for the stockings tonight. You lost the bet." she said with a sly smile.

"Now?" I protested.

"Yep. Let's go mister. March!" she quipped.

I did as I was told and followed her to the bathroom. I stripped naked and was already semi-erect. Sue asked "Is it okay if I do a little more manscaping while I'm at it?"

"Yeah, I guess so. Everything here belongs to you anyway." I said. What else could I say, everything there was indeed hers.

She got the electric clippers from under the sink, snapped on the short length clipper guard and plugged them in.

Sue straddled the tub wall and asked me to stand in front of her. The first task was to trim my pubic area all around my cock. She then pulled the skin taught on my scrotum and buzzed all the hair on my balls, too.

Then she ran the clippers up my legs and got all the hair cut down to stubble.

"There, now let's shave."

She drew a bath with about ten inches of warm water and asked me to get in and just sit there for a minute.

After a minute or so she instructed me to slide down a bit and put my feet up on the wall by the faucet handles. She took a can of shaving cream and spread it over my legs and started shaving. Sue got what she could then asked me to stand. She finished my legs up around my crotch, then took another shot of shaving cream and spread it around my scrotum. She didn't say a word. She just proceeded to shave my balls, too, pulling the skin taught as she worked all around. She opened the drain when she was done and started the shower to rinse me off.

"There, now you're all ready for tonight." she smiled looking at her handiwork.

"But I don't have any stockings." I said hoping that there was a way out.

"You do now. I bought them a couple days ago. I was sooo hoping you'd lose." The twinkle in her eye and her smile made it clear she was enjoying this.

Saturday afternoon we were dressing to go out to dinner. Sue pulled a package out of a drawer and handed it to me.

I laughed "My very own stockings, huh?"

"You're lucky, I was thinking about getting the kind that need a garter belt to hold up. These will stay up by themselves. Do you need help getting them on?" she giggled.

"No thank you. I've seen you do it enough times. I think I can pull it off." I have to admit, I had seen her doing it many times. I loved watching her put stockings on.

As I was pulling and stretching the last one up, I was beginning to get a hard-on. I always loved feeling Sue's legs in stockings, but never realized what they must have felt like from the other side. These gave a whole new dimension to the stockings. The stockings, along with being trimmed and shaved, made me ultra-aware of every nerve ending below my waist, and it showed.

Sue came out of the closet with a pair of dress slacks and a white, pressed shirt. She stopped in the doorway and smiled. "I see that you like how they feel." she said staring at my hard-on.

"Here ya go. These pants will give you plenty of room to swing free."

"I was thinking about just wearing a pair of Wranglers." I said.

"We're dressing up. Remember?" she reminded me.

"Okay."

As I was finishing getting dressed, tucking my shirt in, Sue stripped naked and started putting on a pair of her stockings. She always made me hard when I saw her in just her stockings. Now I was realizing that the wranglers would have been a better choice to hide my cock. It almost looked like a tent pole in these light weight dress slacks.

"Damn, Sue!"

"Yes dear?" She looked at me and smiled. Then her eyes dropped to the bulge in my pants. Without missing a beat, she slipped into a skirt. But I noticed, she didn't put on any panties. She stood facing the other direction and pulled a bra out of the drawer and put it on. When she turned around, I saw it had holes in it to expose her nipples. She just continued to smile and put on her blouse.

"There, all set." she said.

"Not quite." I protested "I can't go out like this. With what you're wearing, and the stockings and everything, I'll be sticking out like this all night. I really should put on a pair of underwear or at least jeans to help control this."

"You can't wear your underwear, remember? But I guess there wasn't anything that said MY panties couldn't go out on our date, just YOUR underwear had to stay home." she said laughing as she turned to pull something out of her drawer. She pulled out a pair of her panties and held them up "Here, you can wear these."

She handed me a pair of very, very sheer panties. "Really?" I asked with a look that must have been a mix of confusion and terror.

"Unless you're ready to go like that?" she said nodding to my crotch.

"Damn, this bet just keeps giving." I said under my breath, but intentionally said it just loud enough to be sure she heard it.

I slid my pants off and her panties on. They were snug enough to keep my erection pinned against my body. I looked in the mirror before putting my pants back on. I saw my fully grown cock, laying to one side trapped behind the extremely sheer panties and only inches away from the tops of the stockings. I thought it actually looked kinda hot, which made me even harder than before.

I got my pants and shoes on and looked at Sue, who hasn't stopped smiling since she shaved me this morning. "We better go before I rip your clothes off and have my way with you." I told her.

"This has been so much fun, you can have your way with me when we get home. Whatever you want to do." she said.

-----

At the restaurant, I just knew everyone was looking at me and knew what I was wearing underneath my clothes.

As we were about to sit down at our table, I whispered to Sue "Am I sticking out? Am I showing?"

As she was sitting down, she looked at my crotch and looked back up at me and shook her head.

While we were sitting there chatting, I leaned forward and whispered "Just so you know, every nerve below my waist is wide awake. Is this how women feel when wearing this stuff?"

"No. Not really. I guess we're used to it. Although I do like how it feels."

-----

On the drive home, I asked her to hike her skirt a little. I reached over and could feel she was already steamy. I slid a finger into the top of her pussy and lightly rubbed the side of her clit.

She reclined her seat a little bit and spread her legs as far as the car would allow. I started dipping my finger down into her hole and then with a slippery finger, swirl around her clit and back into her hole. I could hear soft moans as I slowly stroked her.

She whispered "Better slow down a little or I won't make it home."

When we got home, Sue stood with her arms out at 4 o'clock and 8 o'clock inviting me to do whatever I wanted. She said "Okay, baby. You can have your way with me. But... you have to keep your stockings on."

I unbuttoned her blouse and slid it off her shoulders. Then I got behind her, pressing my body against hers and leaned over to start kissing her neck as I undid the clasp on her bra and took it off. My arms wrapped around her and I cupped and caressed her breasts as I lightly kissed her neck and ears. She closed her eyes and tipped her head back giving me anything I wanted of her.

I took my shirt and pants off and got back behind Sue to resume kissing her neck and caressing her body. I slid a hand down to her hip and unzipped her skirt. It fell around her ankles. I could feel her ass pressed against my cock separated by the sheer fabric of the panties. My right hand caressed her breast while my other hand slid down to find her pussy. I kept kissing her neck as I found her clit which felt hard.

I've always been turned on by her clit. When she gets excited, her clit becomes hard and somewhat erect, sticking out of her lips like a little mini cock. It feels almost as hard as my cock when I have a hard-on. I love going down on her and giving her a clit blow job or simulating a jack off using my fingertips.

"Now to have my way with you." I whispered in her ear. I led Sue to the bed and instructed her to lay down in the middle of the bed face up. I stretched her arms up to each corner of the bed and pretended to tie her to the bed. I told her she was now tied to the bed posts and couldn't move her arms. I then spread her legs wide open pretending to tie her ankles to the bed posts.

Sue was spread across the bed wearing just her stockings. I reminded her "You are tied up and can't escape."

"What are you going to do?" she asked.

"Funny you should ask. I'll be right back."

I returned with a razor, bowl of water, towel, and shaving cream.

"I'm going to enjoy this." I said.

I slid a doubled up towel under her ass. I cupped a bit of water using my hand and made her pussy all wet. I spread some shaving cream all around her pussy and began shaving her. It a few minutes I had her mound now completely smooth and dried off.

I put everything back into the bathroom and came back in. I slipped the panties off to release my raging hard-on and climbed between Sue's legs.

"Now to have my way.", I said. I began lightly kissing her inner thighs working my way to her pussy. Kissing all around, I was careful not to touch her clit. I licked up the entire length of her pussy with my tongue, circling around her clit and going all the way back down. I did this a couple more times, each time Sue pushed her hips up hoping to push her clit into the path of my tongue.

I started crawling up, leaving light kisses up her tummy to her breasts. I kissed and gave light sucks on each nipple while I gently caressed her flesh. In this position, my stocking covered legs were against her inner thighs. I always loved how her legs felt in stockings, but the feeling with both of our legs covered in nylon was incredible, and incredibly erotic, and even a little taboo.

As I moved up to kiss Sue's neck, the tip of my cock brushed against her pussy sending shivers through her body. She pushed her hips upward to rub her clit against anything that she could touch but whimpered when there was nothing there to rub against.

I was straddling her chest with my cock laying between her breasts. Using my hands, I pressed her breasts together, wrapping them around my swollen cock. I made a few thrusting motions as if I was fucking Sue's tits, which was something I enjoyed greatly.

I was feeling like I wanted to cum, but I didn't want to yet so I released her breasts letting my cock rest on her chest.

I moved up a little further, positioning the head of my cock against her lips. Sue opened her lips allowing my shaft to enter her mouth. My hips rocked back and forth, sliding my cock in and out of her sucking mouth. It was probably less than ten seconds when I realized if I kept this up for five more seconds, I would be finishing in her mouth.

I pulled out and started sliding back down, kissing her neck, sucking on her nipples, and leaving a trail of kisses back to her pussy. I gave her a few long, slow licks from bottom to top, and then back down to her opening where I could slide my tongue inside her. I felt the walls of her pussy quivering as I fucked her pussy with my tongue.

I moved back up to her clit with my lips and sucked her clit into my mouth. When I finally touched her clit, Sue let out a loud gasp and bucked her hips. I bobbed my head up and down, sliding her clit in and out of my mouth between my lips keeping suction pressure.

Her hips were meeting my rhythm. With her clit still in between my lips, I slid a finger into her. Sue started whimpering louder, telling me that she was going to cum.

I wanted to finish with her, so I released her clit and positioned my cock at the entrance of her hole. She was so incredibly wet already that I just slid right in ending with my balls against her ass.

She broke the imaginary ropes and wrapped her legs around me and then pulled my head closer for a long, deep, passionate kiss. I felt her legs rubbing against mine and I loved this new sensation of feeling both of our legs covered with the stockings.

Her hips bucked as she instantly started to climax with my cock filling her up. I started pounding her pussy with my rock hard shaft feeling my climax was a freight train that was unstoppable at this point. I could feel her hot pussy juices flowing past my cock when I erupted inside her, mixing our fluids together. I could feel each spasm of my cock shooting one hot stream after another inside her sucking pussy. I kept slamming my cock into her hot hole and she kept pace with me and seemed to be having multiple orgasms.

The room was filled with the sounds of sex. The slapping sound we made as our bodies came together, the sound of our wetness moving together, the whimpering and noises of our heavy breathing.

It seemed like this orgasm lasted much longer than our usual. My cock felt completely drained as I slowed and eventually stopped. Sue laid motionless with me still deep inside her. Every few seconds my cock would twitch which made her pussy walls quiver and squeeze my cock.

We laid like that, looking into each other's eyes. Every twitch was replied to with her pussy walls squeezing my softening cock. Each time, we giggled.

I told Sue "Ever since I put these stockings on, I've been wanting to fuck you sooooo bad. It's been torture not being able to all night. And when I saw the way you dressed tonight, stockings, no panties, I've been extra hard ever since."

Sue replied "Well, ever since I saw you in the stockings, I've wanted you, too. I even went out tonight with no panties just in case neither of us could wait to get home to fuck!"

Then I laid down next to her extending my arm. She laid on her side, her head on my shoulder and placed her leg over mine and her hand on my chest. Neither of us said anything.

With the soft music in the background, we drifted off to sleep.