Loading...Dianne’s boyfriend, Terry, was going to be home soon, so we had to wrap up our special afternoon. I began to pull my pants back up but the load of cum in my satin panties would surely soak through.
“Wait, stop,” said Dianne from the bed, her posture becoming more chaste after her open display of masturbation. Her legs pulled together as her hips turned. “Open the drawer behind you.”
I did as instructed and saw her panties again.
“Pick something and change or you’ll have a big wet spot in your slacks.”
Dreams kept coming true as I looked at the chaotic mess of all her panties. I finally grabbed a satiny string bikini and held it up.
“Very cute! Nice pick,” she encouraged. She turned in the bed, now on her stomach and head barely two feet from me. She was going to watch the whole process.
I got out of my shoes and slacks after some difficulty. Then came the reveal. Luckily, being told by my goddess Dianne to pick and wear a pair of her panties had my cock mostly hard again. I peeled down the soaked panties, careful to not let the cum drip out.
Dianne got a good look at the cum and nodded approvingly. “I think you really liked that.”
“You can’t know how much,” I said with passion.
“I know more than you’d think, sweetie,” she grinned and winked at me. My brain was a little confused but luckily it wasn’t doing much of the thinking right then.
I wiped my cock clean with my panties and began to slip her panties on. I stopped mid-way up my calves. I straightened up, leaving the panties taut between my legs.
“In my fantasies about you, you put the panties on me,” I said boldly. She arched an eyebrow but never lost her smile. She reached out, grasped the ruched satin on elastic waist and slowly, slowly worked it up my legs.
“Very smooth legs, honey. Nice job,” she cooed as the satin caressed my shaved legs. By the time the panties reached up by my cock, I was rock hard again.
“Do you want to wear my panties, John?” she asked suddenly.
“Oh yes please!”
“You want me to panty you?”
“Yes, Dianne, yes! Please panty me.”
With that, she slid them up. I was frankly stunned that they fit so good. She must have seen my face.
“They fit because you are skinny like a girl NOT because I’m fat!” she snapped in fake irritation before laughing.
“How did you know?”
“I saw the tag in one of your photos.”
The perplexed look on my face must have been priceless because she started giggling. When she recovered herself, she began to get off the bed.
“When you gave me your memory card of the high heel photos, you forgot that you had some other photos already on there…”
My head rang as if I’d been hit by a hammer. Of course! That’s how she knows what I want, knows what I do, even knows my lingerie size. I sat down on the bed as she put her work blouse back on. My face was blushing bright red and I was trembling. All my fears of my desires being discovered, long established and deeply driven in my psyche, tried to overwhelm me. Even sitting in a woman’s bedroom wearing her panties was not enough acceptance to undo the work of years.
She saw my distress and sat next to me, slipping her arm around my lower back to hold me.
“You knew everything and that’s why we… did this?” I finally asked.
“I think it’s been pretty obvious that I have a crush on you,” she began. “And I think you have the hots for me too, right?”
I nodded. She lightly pinched my bottom through the satin. “That was rhetorical!” We both laughed, relieving a little of my sudden tension.
“But you also get it! You understand about heels and lingerie and all the beautiful clothes in the world that can feel so amazing! They look beautiful but combined with the beauty of the human body they are taken to a higher level, so… so… intoxicating. I don’t think I’ve ever met someone who has a love for this stuff like I do,” she explained. “Any girlfriend I’ve ever brought it up with thought I was crazy. To them, panties are just underwear: too expensive, don’t fit, and doesn’t make them feel sexy. I never figured out why I was different, but when you wanted to photograph my shoes… when I began to suspect there was someone else out there who understood… and then when I saw your lovely photos… seemed perfect.”
I was amazed to have found such an amazing woman. I never dreamt a woman would understand or enjoy lingerie and being girly quite like I did.
“Now I’ve got to have rules. Either accept them all or we can’t let this happen again.” So close I would have agreed to anything for her. I nodded.
“For now, lets take this slow. No one else can know we’re doing anything here Wednesday afternoons except work on the Higgins account. Either of us can stop it at any time, no reason required. I want to stay friends even if this doesn’t work.”
“I agree completely,” I blurted but she shushed me.
“I won’t let you touch me sexually because I won’t cheat on Terry like that. Can you live with that?”
I did pause at that. My desire was so fierce for her that to be brought so close without being able to touch her… and I thought strip clubs were frustrating. I made my decision.
“I could walk on broken glass if it meant we could… play… like this again,” I assured her.
“Serious, John. Swear you can handle the conditions.”
“I can handle them, Dianne.”
“Okay good. This is a good thing. We are good friends. We care about each other and want each other to feel pleasure. Nothing more than good friends sharing a hobby, right?”
“Best hobby ever,” I grinned.
“Yeah,” she admitted before shoulder bumping me. “Now seriously, you have to be out of here.”
—
My mind was in a haze of excitement, anticipation, and replaying a loop of remembering our afternoon. The next day Dianne came by my office and quizzed me on the color of my panties. She took a guess (pink, correct), then I took a guess on her panty color (blue, also correct). Friday it became a game of dare, each of us undoing our clothes just enough to clearly show the panties and their color. It may not seem like much, but in our open office it was a real dare.
Over the weekend I had to tamp down my desires. I couldn’t obsess over this amazing development or it would kill me to wait until Wednesday. I didn’t call her or text her. It just seemed like crossing the line with her and Terry. I tried to keep my emotional balance by filling my days with friends and activities. It worked mostly, but I was distracted from time to time.
The nights were hardest to not masturbate and think about it all over and over. I even wore a regular t-shirt and boxer shorts to bed to reduce my steady arousal level though they were too uncomfortable and I soon switched back to satin panties and a satin baby doll top. Waiting for Wednesday seemed like it was going to take forever but it was not as long as I expected.
“Come on, we have an extra meeting with Higgins to go over last quarter’s figures. It’ll take all afternoon,” announced Dianne within earshot of my co-workers just before lunchtime on Monday, two days early. I could see by the flash in her eyes that she was a little worked up in anticipation.
I gathered my coat, my laptop and papers and followed her out, my heart beating fast. We got into my car and headed out into the building’s parking garage. I enjoyed following her, watching her walk in the high heels, her hips swaying. She was wearing a tight knit skirt, a sheer multi-layered blouse, and at least 3″ Jimmy Choo heels. After reaching my car, she glided into the passenger seat of my Audi.
“You know, I’m not feeling hungry. My place?” she asked rapidly. She was flushed. I smiled broadly and nodded before hitting the highway.
We drove along exchanging flirty glances. Even though we’d been making this drive for a few months for our real work, having her in my car was a new experience. I could smell her perfume more vibrantly and glance at the luster of her hair.
“I’ve got something special planned for you,” she said at last. “Took me a lot of research but I know you’ll be thrilled.” As much as I questioned her, she wouldn’t spill the secret.
We reached her house and I parked my Audi in the driveway on her side leaving the side Terry used open. I made sure to grab my laptop and papers in case nosy neighbors were watching. It dawned on me that even though we had our rules I now felt like we were carrying on an affair. I pushed it out of my mind. ‘Sorry, Terry, but I need this.’
I followed her into her house and she led me to her bedroom.
“Okay, girlfriend, you need some TLC. Mother Nature gave girls hair in different places that just aren’t attractive. If you’re going to be my sexy girlfriend, you need to be sexy smooth. I’ve got just the solution. First, you will have to strip,” she informed me with a wink. Settling herself in a stuffed chair, she got ready to watch me disrobe.
Her words and phrases were electric to me. I desperately wanted to be her girlfriend.
Being a fairly good dancer, I tried to make my movements sensual, a real erotic tease. First tie, then shoes, shirt then slacks. After my socks I was left in a pair of silver satin panties and my t-shirt. Dianne smiled and idly touched one of her breasts for a moment before remembering herself.
She stood up and walked up to me, slightly taller due to her heels. She took the bottom edge of my t-shirt and pulled it slowly up, holding my gaze with her own. The tension in my body was thick and my cock ached from its intense erection, so close to her.
The t-shirt went up over my eyes and past my chin and lips and stopped suddenly. My lips were covered with hers in a deep and passionate kiss. She truly took my breath away and danced against my tongue with her own. As soon as I reached out to pull her to me, she moved away and pulled my t-shirt off all the way. Her face was flush and her breasts were rising and falling eagerly.
“You need to head into the bathroom,” she said, her voice constricted. The kiss went unspoken though I began to suspect that our no touching pact might not last long no matter our best intentions.
“Take off your pretty panties and step into the shower,” she instructed. I complied, my erection jutting out from my body solidly. She turned on the water, adjusted it to fairly hot and switched it to the shower nozzle.
“Give yourself a good clean first.” As she watched, I used her scented soap and shampoo and get nice and clean. At times she bit her lip and I knew she wanted to be in there with me.
When I rinsed off, I turned to her, almost daring her to touch my cock or me. She got very close before turning away and putting a special trap over the drain.
“The next step needs some care. Don’t get a drop of it above your neck or you’ll lose your eyebrows or hair.” She handed me a plain bottle. I poured out the pink liquid, rubbed it into a lather and began to rub it all over my body.
Having Dianne’s eyes on me made sure I remained rock hard. I tried to pay attention to what I was doing and I was surprised when her hands moved over my back.
“It’s hard to get perfect coverage on your own,” she said softly as her hands explored, massaged, and rubbed the special lotion in. When her fingers massaged my bottom I moaned softly and felt my cock throb. She urged me to spread my legs and I felt her fingers truly exploring me, covering EVERYWHERE with the pink lotion.
I could fell a tingle all over my skin. Every inch was soft, smooth, and sensitive in the best way. I felt like the lightest touch on my cock would make me explode.
All too soon, it was time to rinse. I watched everything swish down my body, unimpeded by mainly hairs.
Dianne was not in the bathroom. I toweled off quickly, enjoying the sensations and then put on a pink satin thong she’d left for me. I found her in the bedroom.
“I’m sorry, but you look so… I just had to come cool off a little,” she said, blushing. “But you’re all ready for the best dress up you’ve ever had. Pick what you want, anything you want.” She gestured broadly across her entire wardrobe.
“Are you serious?” I asked, stunned.
“Honey, it’s fate that we’re the same size. Aaaand it’s fate that we share this special… hobby. Now I want to see my girlfriend doll up.”
I stood there so excited to see her recline on the bed, to feel my skin glowing, to feel perfectly accepted in tiny panties. It was a dream even if was only going to last a couple hours. I smiled and looked in her eyes. It would be perfect if only she wasn’t dating Terry.
I refused to ruin the moment and shook that seed of frustration out of my head. It was much more fun to walk into Dianne B’s walk-in closet, feeling all of her clothes rustling and swish against my tingly skin. My own puberty fantasies came rushing back. I touched her jeans, her skirts, her blouses and dresses.
When I reached the end of the closet, I was facing her lingerie collection, the special pieces that needed more care than a panty drawer. I saw the rich red satin bustier with dangling garters and fell in love. I lifted it down from the hangar and looked around. A white satin mini-dress and a pair of white strappy high heels practically jumped into my arms.
“Very hot!” she said from the opening of the closet. “You’ll need these…” holding up thigh high stockings and red string bikini satin panties “and these…” holding up a small plastic bag.
Walking out to the bed, I sat on the edge and laid the clothes out with care. “What’s that?”
“Once I really knew what this was, what my friend was hiding, what… what we started, I knew I wanted to help you.”
“You’ve made so many of my dreams come true, Dianne,” I said, feeling almost teary with the intensity of my emotions.
“Well, get ready for the next dream. Now close your eyes and sit still.”
With both eyes closed I waited. I felt her kneel in front of me and my distracted half-hard cock got fully hard.
“Not that, honey. Not that it isn’t tempting…”
I swallowed hard, trying not to cum in the panties.
Her fingers touched me, lightly across my chest. There were no chest hairs to brush against and her fingertips felt like she was stroking my penis. I trembled with pleasure.
“That soap is pretty special. I came once trying to get dressed after I used it the first time,” she confessed. Her hands kept exploring my chest, massaging it, probing it. I gasped when she pushed some sort of cold gel on my skin, spreading it around. When her fingers left again I fought to keep my eyes shut.
It pressed against my chest turning the cool gel warm. It was soft and supple and I was sure that Dianne had just pushed her breast against me. When it was joined by her other breast I couldn’t stand it and my eyes flew open.
Dianne was still clothed and eased away from me. I looked down and saw my breasts. They looked like my skin and if I squinted the line where they stopped disappeared. Seeing the swell of breasts on me was overwhelming. I felt their weight pull on my chest.
She moved close again and shifted each breast a little in the clingy gel until she finally smiled a wide toothy smile.
I felt the weight of the breast forms on me and I reached up to touch them, to cup them, to squeeze them.
“Holy crap!” I blurted. “They feel real!”
“Top of the line…” she giggled as she undid her blouse. An unsnap of her bra and I was seeing her breasts for the first time. “See anything familiar?”
Glancing down and then across, I realized that she’d bought me her breasts. “If we’re going to be swapping clothes and lingerie, you can’t have a bigger chest than me!” she teased. “We’re both a full C now.”
I moved the breasts in my hands and felt like I was feeling up a girl, a girl who was me. They didn’t seem to want to come off. I glanced up worried.
“We can take them off with a special solvent that came with them but it’s your choice when to do it. You might want to keep them to play tonight at home,” she said with a wink.
I was overwhelmed. I was so aroused, so touched, and so taken with her that I stood up and hugged her. Our breasts moved together and I pulled her body close. Her hair smelled wonderful and I realized in that moment that I would have given up every fetishy fantasy cum true to have her be my lover, my love, all mine.
She drew back slowly and I placed a hand on her heavenly breast, there for just a moment before we both stepped back.
“Against the rules,” I said finally, resigned and confused.
“Against the rules,” she breathed, pulling her bra just enough over her breast to cover her nipples. “Let’s get back on track. You still owe me a dress up.”
She moved back onto the bed, propped up on pillows at the headboard, ready for the show.
First came the bustier. My fingers ran happily over the rich red satin, expensive bridal quality. I felt the long boning down the torso and the cups for the breasts. It had an inch of black lace trimming the bottom edge and black ruched satin bordering around the top. Thin nylon shoulder straps attached to the top edge behind tiny red satin rosettes. The rosettes repeated on a bit of nylon hanging over the clips of the garters which hung down. Dianne had exquisite taste.
Being no novice at donning lingerie, I pulled it around my torso backwards adjusting to stay below my new breasts. I proceeded to clip the back of the bustier shut, grinning as I ran into the issue of seeing past my breasts.
“Welcome to girly world, John,” laughed Dianne. She paused. “Or should it be… Jane?”
I looked up and nodded.
“Okay, Jane it is! Hi Jane!”
“Hi Dianne,” I said softly, feeling like another boundary had been crossed without knowing truly what all the consequences would be.
I returned to my task and finished hooking all the plastic hooks and eyes together. The bustier was very tight against my skin and it felt wonderful. I carefully began to shift the piece around my body, an inch at a time, until it was turned right-side-round. I moved it up carefully until my new breasts settled easily and firmly into the cups.
Dianne slid off the bed and moved behind me. She pulled and tugged on the bustier until it sat a little higher on me and lifted my breasts beautifully.
“Gotta show off the ‘girls’, Jane,” she teased before resuming her comfortable position on the bed.
I glanced in the mirror above her vanity and noticed how the bustier was shaping me a little toward an hourglass. I definitely felt the squeeze and thought it looked like I had some hips.
Next I sat on the edge of the bed. I rolled up a stocking in my hand, slipped it over my toes and then spread it up my leg. The silky nylon against my smooth, sensitive skin felt amazing. I clipped the stocking to the bustier’s garters and repeated the process. Standing up, feeling the tug on the bustier and the shifting on the nylon all over my legs made me moan. If Dianne had as much as breathed on my throbbing cock, I would have exploded in pleasure.
“Janey likes!” laughed Dianne eyeing my cock. I swallowed and nodded before picking up the panties.
I’d learned early on that I love the feeling of panties OVER garters. Panties under garters just made everything harder but wearing them over the garters meant you were ready to play. I’d never had to put that to the test before but I knew it made going to the bathroom easier when I was dolled up. I also loved the extra sensation it gave my cock with the partially suspended panty fabric sliding across my erection.
I slipped the panties on slowly but got them up and around my bottom nice and snug. Shifting my cock to the side, I was able to keep it inside the panties, for now.
Next was the dress. It was a gorgeous confection of satin layers. I lifted it up, oriented it and then stepped into it. Drawing it up my body was a dream especially as Dianne and I’s eyes locked on each other during the process. Slipping my arms through the holes, I felt the material slide on to my shoulders. The bottom hem was teasing my thighs above my knees but not high enough to flash my stocking tops.
I reached behind me to zip it up and did pretty well. I walked over to the side of the bed and showed my back to her. She finished the zip making me shudder.
My collection of fetish moments is wide and varied but zipping into a dress was one of the most special. I think it was a combination of the purely feminine feel of zipping into a garment married with a delicious sense of being trapped in the dress, unable to unzip it quickly and get out of it. The chances of being caught dressed went up when that zipper went all the way up. Especially since on my own it sometimes took me a minute or two to get to the zipper again and winkle it down enough to slip out.
I swished to the edge of the bed again and put one foot into one of the heels. It felt surprisingly comfortable, broken in. I buckled the ankle strap and repeated the process with the other foot. Standing, I swirled around and stopped to look at Dianne.
Her skin was flush and she’d moved her skirt up around her waist, her hand moving quickly against her panties. Without words, she got up and pulled open the drawer of her nightstand. She fumbled with a box but then handed me a condom. So much for resolutions, I thought.
“Don’t get excited, I just don’t want you to splooge my favorite dress. It would be a bitch to get cum out of it and there could be some awkward questions,” she explained quickly but still distractedly. “Now lie back on the bed and grab the headboard.”
Her headboard had carved posts in it giving me an easy place to hold on, a mandate that would become a Herculean task in moments.
Dianne moved on top of my body. I felt her weight on me, felt her heat, smelled the mixture of her perfume, her skin, and her sex. Her face was a glow of arousal as she leaned down to kiss me.
Unlike the stolen kiss with the t-shirt, this was straight out passion. Our lips moved smoothly against each other, wet and supple. Her tongue tickled mine, our mouths open. I felt her hair tickling my face with her above me.
She finally pulled up, panting. She placed her hands on my forearms, holding them down beside my head. She started to grind her pelvis against me, working her skirt up and sliding deliciously over my femme and dolled-up body. She finally found my cock through the layers and focused her motion. Biting her lower lip, she rode against the ridge of my cock. Luckily the condom and the layers dulled the sensation for me or I’d have cum.
After a few minutes of our bodies moving against each other, she raised up, moving her hands to my breasts, squeezing and groping them through the dress and bustier. She slid her hips down my legs and laid down, pulling my dress open and pushing the cups of the bustier down. I watched as she licked and sucked my erect nipples, hearing her moan as she made love to my faux femininity.
I reveled in the feel of her on me, the press of her breasts against my groin as she enjoyed my breasts, our clothes shifting and sliding against each other and over me.
My knuckles were white as I gripped the headboard. I desperately wanted to touch her, to pull her to me, to have her mount me or something. But I didn’t want to pop this erotic balloon. If she wanted to bend the rules, she had to take the lead. I was getting more than I’d ever dreamed and I struggled not to get greedy.
Her pussy moved against my knee and suddenly she was rocking on it, shifting her drenched panties against my nylons. I felt her body tremble and her legs locked on either side of mine.
“Oh god Jane yes!!” she moaned as she shuddered, her hands firm on my breasts, pulling on them. I felt her body cumming against mine and I couldn’t stop. My balls clenched and I throbbed again and again, pouring cum into the condom, stretching it down under all the material.
We clung to each other during the peak and then as we each relaxed into the glow. I watched Dianne’s face as she regained herself, our eyes watching each other. She slowly got up off of me, brushing the dress down as she moved down and off the bed.
“wow,” she finally said. I sat up, shifting in the dress and lingerie, still pleasurable although the mind-wrapping intensity of it had ebbed a bit.
“yeah,” I replied. We sat there for awhile and then I got up.
“You look gorgeous in it,” she said quietly, reaching up to stroke the dress into position over my faux breasts.
“I feel gorgeous. I feel gorgeous.”
We both knew we were forging new territory, blurring boundaries. We didn’t talk as I undressed. She showed me how to use the solvent and carefully remove the breasts. I cleaned them and put them in their protective case.
Dianne gave me a chaste kiss on my cheek as I left her home and got back into my car.
I’d never imagined it could happen and I had no idea where it was going, but I knew I couldn’t wait to keep going on the ride.