What You Let Slip

I wanted to kinda tell the story of my last relationship and my partner who helped me become a bigger sissy. Most of it is true with only a little embellishment. I owe everything to her for helping me be who I am now! I hope you enjoy this first part of the story and I hope to do more of it soon!

What You Let Slip

By SashaySasha

We had just spent the night out at a party and had been drinking heavily. Jen walked in the door and turned around to me. She was always so stunning to me, her long red hair had a wave to it and played pale skin and emerald eyes. She was tall, about 5'9" and had extremely long longs, only made longer when she wore heels. And whenever she did wear heels, which was often, she was always taller than me. I was only 5'10" and I loved how I had to look up to her when we were out. I know she loved being taller than me too.

A smirk appeared across her face, "I hope you can still get that bad boy up after all those drinks, mister."

Chuckling and leaning against the door frame to keep my balance, "I'm sure it can, why don't we find out."

She led me to the bedroom. We kissed hard and then laughed, we were almost too drunk for this. She pushed me back a bit and I fell onto the bed. She giggled and started taking off her dress. Underneath, she was wearing the most exquisite lingerie. A nude garter and panty set with lace sat at her waist attached to suntan stockings. She knew how much stockings drive me wild.

I began stroking her legs, feeling her soft skin through the material. Being more than a little drunk, I let slip something I shouldn't have. "God stockings are so sexy, you always look so amazing in them! I wish I could know how that felt."

Her being drunk as well, "Really?! You should try some, it feels SO good!"

***

I woke up the next morning. My head was throbbing. Jen was cuddled into me and we were under the covers. I went to scratch my shoulder feeling a strap. I realized immediately what happened last night. Trying not to wake her, I got out of bed. I stood there, silently, trying not to wake her.

Slowly, I walked into the bathroom and turned on the lights. Taking everything in as I saw myself in the mirror. I was wearing a maroon pair of panties with a matching lacy bra. On my legs were a pair of hold up tan stockings. Instinctively, I rubbed my legs together. My cock was as hard it has ever been at its full 6 inches. I heard her behind me.

"Hey there sexy. I thought I dreamed that all and I'm glad I didn't."

"I-- this was just a joke. I was just joking about this." I stammered out as my cheeks went flush.

"Oh no! You're not getting out of this. You know what they say, you're the most truthful while drunk, and buddy, this is what you want. And we're going to explore it. You said some interesting things last night and I have never gotten so turned on by anything before so we're doing this." A mysterious grin overtook her face.

"I mean, okay maybe I really like lingerie and I especially like it on you but I don't want to wear it!" I knew I was lying, so did she. I was practically bouncing, rubbing my legs together enjoying the feel of the stockings. I loved lingerie and always had. I was always jealous of girls, jealous of Jen, and wanted to feel what they felt.

"That's not what you told me last night, and not the only thing! We're going to have some fun and I think you're going to love it." She winked, coming in behind me. "Are you saying you aren't loving this?" She started stroking my hard cock through her panties.

I quivered under her touch, "I don't--" I let out a moan. "I don't know. But how far do you want to take this?" I saw her smile behind. The image of me in the lingerie combined with her squeezing my cock was like a dream. Was this something I really wanted?

"Why don't we try something today? And if you really don't like it we don't need to continue." She continued to stroke, I knew I was close to exploding. "Because I'm pretty sure your little man is looking forward to it." Little man was all it took. I exploded in her panties. "Oh wow! I don't know if you've ever cum that much with me before! Yeah I think you're going to enjoy this." She smiled evilly behind me.

***

I sat there in her lingerie thinking the whole time, slowly stroking my legs. My cock was already hard again and stayed that way while Jen was showering.

She came out, with just a towel wrapped around her, drying her hair. "Yeah, I think this is what you really needed." Smiling, looking at my panty encased penis.

Jen quickly got changed. Looking back at me, she tossed a can of shaving cream and a razor my way. "While I'm gone you need to shave your legs."

"But--" I stammered out.

"No." Sternly, "You need to try this, all out. Everything you said last night, what happened in the bathroom earlier. Right now! You're harder than I've ever seen and not even phased by the still wet cum on those panties." She came up to me, spreading my legs. "Tell me you don't want to know how this all feels when you're properly smooth."

I looked down, her hands were rubbing my thighs. My cock was throbbing in these cum soaked panties. She was right. "I-- want to know."

She tilted my head up, kissing me quickly on the lips. "Good! I can't wait to help you. Now, go in the bathroom and get out of those cummy panties and start the shower.I have to run out and grab a few things, you better be all smooth by the time I get back. And don't you dare jerk off!"

I slowly walked to the bathroom as she left. I was so nervous about all this, why had I told her. But I couldn't deny I wanted this. Jen was being so assertive, she's never been like that. I started to peel off the ruined panties, still seeing the moisture from my cum, it did gross me out a bit. Letting them fall, began taking off the rest. The bra was much harder to take off myself than it was taking it off Jen.

Letting the water warm up, I grabbed the razor and cream and stepped into the shower. About forty minutes later I came out smooth. I took some lotion Jen had left me on the counter and began rubbing it onto my now smooth legs. My cock was throbbing this entire time.

Leaving the bathroom, I didn't really know what to do. I saw the panties I had just been wearing, the cum soaked panties, and I slowly reached for them. I sat on the bed with them in my hand, slowly rubbing my legs together. I had no idea having smooth legs would feel this good. Taking the panties, I wrapped them around my cock and started stroking. My legs were so smooth and I kept rubbing them, slowly stroking faster.

Jen came through the door with a large bag, with a shocked then angry look on her face. "Are you kidding me?! I was only gone an hour and you're already jerking again. I told you not to!"

"I-- I'm sorry, Jen! It's just everything that happened and now how smooth my legs are, I couldn't help it!" I blurt out.

Jen, dropping her bags, came over to me smacking my hand away from my cock. The soiled panties fell to the ground. "And you're using those cum soaked panties too, go clean them in the sink. When you come back in here, your hands better be behind your back, mister,"

Shamefully, I took the panties to the sink and began to wash them. When I came back in, Jen had laid down everything she had bought while she was out. There were several pairs of panties, all very lacy. Three bras, one black, nude, and white. Two packages of stockings. Two dresses, one floral and the other silky. And a box that was not opened.

Jen stood at the bed, not yet turning to me. "This was-- a lot. I know, but I want you to feel how I feel." She turned, looking down at my cock, still fully erect and dripping. She smiled, "But you have to listen to me. No more jerking your little cock."

I snapped, a little shocked, "Little?"

Jen came over to me and stroked it and I moaned. "It's not the biggest but that's okay." She pumped a few times, "It'll fit better in your panties." She emphasized the "your". I thrust my hips forward a bit. "I like your size, it's cute, for a sissy."

I EXPLODED. Jen's eyes grew huge watching as I came, trying to catch it all. I buckled at my knees moaning. It spurted up her arm and then started to subside, oozing out. My cock finally started to deflate after it being hard since I awoke.

"Holy shit." Jen let out. She brought her hand to her mouth and licked a little of my cum up and moaned. She then quickly started taking off her sweats, "Get on your knees right now." There was something different about the way she said that, she sounded so horny.

I dropped and began helping her with her panties and she pushed my hands away, a little of my cum flew to my lips as she did. Without thinking I licked it up, realizing what it was. I made a face.

Jen had her panties down, and grabbed my head. "Start licking--" she gasped out.

I did. Her pussy was so wet, I had never seen her so turned on. I slowly started licking, I always loved taking it slow when I went down on her.

"No, EAT me now." She moaned, pushing her mound deep into my face.

I started sucking on her clit and she started gyrating on my face. She started squealing like I've never heard before and then came, gushing.

She fell to the bed, gasping. "Oh my God. I-- I've never came like that."

I was still kneeling, a little shocked at what all just happened. Her juices all over my face.

Catching her breath, she looked at her hand, still covered in my cum. "You've never cum like that." Smiling, she walked up to me. "Look at all this, I called you a sissy and you burst all over me! Is that it, do you want to be my little sissy?"

Flabbergasted, I looked away. I knew it was what I wanted, in my fantasies, from those stories I read, the captions I saw. Softly, I let out "Yes."

She grabbed my face, my cum coating the side of it. She then kissed me, hard. "I'm so fucking hot right now, my little sissy. Let's get you dressed!" I raised my hand to my face, it was covered in my cum and felt disgusting.

After cleaning up, Jen brought me back out into the bedroom. She handed me a pair of white lace pantied with a little bow in the front. "Put these on and I'll help you with the bra."

I slid them up my legs and it sent shivers through me. Nestling it in place, my cock was starting to get hard again and Jen noticed. "Okay, we need to tuck that," pulling up a video on her phone, "watch this, it'll help." A very done up drag queen was on screen showing how to properly tuck. "We'll have to get you a gaff at some point to help you stay smooth all the time but this'll work for now."

After situating everything between my legs, Jen came behind me and helped me put on a matching lace bra. Once strapped, I noticed the cups grabbing the little flesh I had and pushing it up. I had small little boobies.

She picked up a white garter belt and wrapped it around my waist. "Sit down, I'll help you with these stockings." She opened a pair of nude stockings and started sliding them up my legs, I could feel my cock try and get hard and I let out a little moan. Jen just smiled.

Kneeling between my thighs, she slowly rubbed both my legs. "Don't you just love how this feels? So soft and delicate. So sensual. Do you feel that pull of the garter? I love that feeling, like my lingerie is grabbing onto me." I closed my eyes, enjoying everything Jen was doing. I let out another moan.

"Let's get you into this dress." I opened my eyes to her holding up a silky looking cream dress, "I think it'll go well with your skin. I love this material. Just wait until you feel the silk on your stockings." She helped me up and slid the dress over my head. I shivered as it fell into place. Taking my hand she helped me over to her vanity and had me sit.

She brought the box over with her, revealing a pair of nude heels. Intimidating heels. They were only 3" but I knew I'd have trouble walking in them. "You'll need to get used to how these feel, they will form to your feet a little bit the more you wear them."

She took my leg in her hand, and guided my foot into the shoe like a princess. She rubbed my calf a little, smiling up at me. "I know they're daunting at first, but you see me in higher than these all the time. You'll get used to them." She had me sit still, with my knees together, something else that would take me a while to get used to.

Next, Jen got out a brown wig that she used last halloween. Placing it on my head she pinned it into place and it laid just past my shoulders. She brushed it out a little, I think this'll work fine for now." She then got out some of her make up, "We're just going to do a simple look for right now."

She took her time putting the makeup on, I just sat in a daze as she did. The last thing she did was get out some red lipstick and had me purse my lips. I was very excited as she put it on. Finishing, she got up "Alright, are you ready to take a look at yourself, sissy?"

I was dazed, ready to see, ready to look at myself dressed like this. Her sissy.

Jen helped me up, as I wobbled a bit in the heels. "You're going to have to work on walking in those because you'll be wearing them a lot here." I didn't want to let on how excited I was about that but I knew she saw me smile.

We walked over to her full length mirror. I gasped moving my hands quickly to my face. I looked okay, not a girl but not very masculine at all. I swished around feeling the dress on my thighs, rubbing my legs together and I let out a moan. Jen just stood back and watched the whole time.

I finally broke out of my daze when I saw a flash. I turned around and felt my wig swing and hit me in the face. There was another flash. Jen was smiling, holding her phone up. "I just wanted to have a first dress picture of my sissy."

"No, please! Don't--"

"I'm not going to share these! I just wanted some pictures, that's all. But I guess I do have a bit of blackmail now, don't I, sissy?"

***

I spent most of the afternoon having to walk the house, learning to deal with the heels. As much of a pain as it was, everytime my heels touched the tile or hardwood, I felt my cock twitch between my legs. My heels were clicking. I loved it.

"I can't wait to see you in taller heels, you actually have amazing legs." Jen said sitting in the living room and she was driving me wild. She was wearing an emerald dress that matched her eyes, it barely covered the lace of her black stockings. Standing up, she came over to me. Even though I was wearing 3" heels, she stood over me in her 4.5" heels. "I love that you still have to look up to me like this. I'll be honest, it's why I always wore heels before. I loved towering over you." She leaned down and kissed my forehead.

I watched her walk over to the kitchen, swaying her hips more than usual. "What do you want to eat tonight? We really don't have anything in here." She was bending over and sticking her ass out. I wanted to go over and rub into her. Turning around "Should we order take out?" She looked at me, I had both my hands at my crotch as one foot floated, twirling on it's toe.

She started giggling, and sashayed over. "Sissy, you can't go around just grabbing your crotch like that! It's not very ladylike at all." Placing her hand over mine, "Are you horny?" Jen leaned in, pressing her body to mine. She put one of her legs between mine and rubbed them causing me to moan. "Do you like that, Sissy? The feel of our stockings rubbing?" Tilting my chin up, she kissed me. I moaned again, leaning into her with my arms around her neck.

Jen leaned back, breaking our kiss. "God, I love you like this. You're so cute and girly already!"

I looked down and away, my arms still around her.

"Hey, look at me. Tell me you don't love this."

I slowly looked up to her, into her beautiful green eyes. "It's just so much. I-- I do love how all these clothes feel. Especially the stockings. My feet do hurt but I don't think I'd ever feel this girly in my life. And yes, I'm extremely horny."

Jen kissed me again. "I'm glad you like it so much. I can't believe how much I'm enjoying it!" She stepped back, leaning against the counter and slowly pulled up the hem of her dress revealing she wasn't wearing any panties. "Just look at how wet I am, because of you." Her fingers now between her thighs, spreading her lips. She moaned loudly. Bringing her finger up, it was coated.

"Come over here."

I slowly walked over, extremely aware that my cock was trying to escape from my panties.

Jen pointed her finger towards my mouth, "Suck." And I did. Jen moaning, she began to push her finger in and out of my mouth. I reached down to touch her and she slapped me away. "No hands, just keep sucking."

I closed my eyes as I sucked on her finger, still tasting of her sweet.

She began moaning more, I looked down and she was fingering herself. She looked deep into my eyes, there was intense lust behind them. Vigorously, she was probing herself. Her finger still in my mouth she grabbed my chin to balance as she let out a loud groan.

I just stared at her wide eyed as she came. Her face in passion and continuing to moan. She took her hand from between her legs and it was soaked. Looking at me, "Clean this off would you?"

I fell to my knees, taking her arm, I began sucking each of her fingers. She tasted magnificent. Licking her palm she put her other hand on top of my head, "Clean up between my thighs too."

She backed up more, now sitting on the counter. Her legs were open and soaked. I could see it beginning to drip down onto her stocking tops and that's where I started. Kissing below the lace I heard Jen let out a moan. I began to lick up to her exposed thigh, craving her taste. Her pussy was still dripping wet and I took a lick causing Jen to grind into me.

"No. Not right now, I'm a bit too tender, just clean up the mess you caused." Running her hand through the wig on my head. I continued to lick and kiss her other thigh clean. Savoring the final tastes I sat back on my legs, looking up at Jen. She looked like a goddess. Her long stocking encased legs around me and pussy still in full view, I just wanted to be in her.

She looked down at me, still recovering. "You look so good down there on your knees. A good little sissy. My sissy."

My cock flexed, painfully this time and I let out a gasp. My hand shot between my thighs. Jen just laughed, "We'll take care of that later. I can tell how horny you are."

Pulling her dress down, "We need to figure out what we're going to eat tonight. I know you're happy eating me all evening but I still need some nourishment." She said with a wink. Putting her hand out, "I'll help you up."

Once on my feet, I tottered a bit. "Jen, can I take these heels off?"

She spun her head around at me, "No. You need to get used to them. You're going to be wearing them around here a lot more."

I looked down, seeing my stockinged legs and heels. I did love how I looked, how I felt, but how far did I really want this to go? "What do you mean more?" I asked, tentatively.

"Don't you want to keep being my Sissy?" She looked into my eyes, longingly, and pouted her lip.