tagTranssexuals & CrossdressersA Learning Experience Ch. 03

A Learning Experience Ch. 03


This is chapter 3, Jack wakes up with a Pink Baby Doll hangover at Andy's house and starts a long trip down a very deep rabbit hole! Will he be Jack for much longer? Or is it time for Joscelyn to take control? Cheers! -- Joscelyn

After admitting a long held secret desire to become a woman to my three best friends at college, they have rallied around me, and we've just become the latest members of the infamous Mile High Club. Andy took us all flying at about a mile in the air and we all had sex, thus qualifying for membership. We had then gone out to a wonderful little restaurant for a fine dinner. But I had just a couple too many 7&7s me thinks...

Ah, to dream... I was somewhere in my usual morning wet dream, the lesbian orgy.

Then, at some point, the real world broke onto my consciousness the same way a raw egg gets broken onto a hot skillet, but the only sensation I had sounded like someone hammering a huge piece of metal. Then I realized that a sharp pain was accompanying each hammer blow, at about two blows per second. I had to find whoever this was and get them to stop, so I gradually tried to open my eyes, but the light in this place was absolutely blinding. Then I had my first complete thought, 'where am I?'

I desperately tried to remember. Anything would be good. But it felt like my head was full of liquid concrete. Again I tried to open my eyes, forcing them to focus on whatever they could, and slowly the white haze began to contain vague shapes. I barely made out the footboard of a bed, and based on where it was, I thought it probable that I was lying in that bed. The incredibly bright light was morning sunlight streaming in through a window to my right. Now I could begin to see beyond the bed, and there was a chair in the corner with a chest of drawers next to it. It had a mirror hung over it, and to the left were a pair of closet doors, and then further left there was a single door, probably the room entrance. This must be a bedroom, but whose bedroom?

Oops, something just moved, and it wasn't me! As I quickly looked down to try and discover who or what it might be, I knew that pretty hand with the French manicure, lying on the covers. I immediately rolled over to see my girlfriend Melissa's sleeping body. Rapidly blinking several times to purge the sleep from my eyes, I looked down at her fragrant hair, beautiful face, delicate neck, and gorgeous breasts encased in a sexy black baby-doll nightie. I smiled on this delicious scene, but then my brows furrowed, as I had to wonder what was she doing here? For that matter, what was I doing here, and finally, where was here?

Just then Mel's eyes fluttered open and she smiled her usual big smile, then wrapped her arms around my neck and kissed me deeply for several minutes. With that one kiss all my worries seemed to disappear. When she finally decided that we needed air, she gave a long moan, "Mmm, you still taste good baby..."

"Mmm, you taste pretty good yourself, babe!" I said, "Oooh, I just wish I could get this lil' guy running the jackhammer in my head to shut it the hell off."

I put my hands over my eyes to keep out as much of the sunlight as possible, then let out another pitiful moan to see how much sympathy I could generate.

"Ha, ha! Ok, I get the hint, I'll baby ya just this once," Mel said as she got up and put her robe on over her nightie, "One hangover special, comin' up!"

After she left, I thought about dealing with an unruly bladder, but as soon as I took my hands away from my eyes, I thought better of it. Probably best to just not move, that's the ticket! Wait until Mel gets back with the cavalry, or at least something to tame the guy in my head with the huge jackhammer. Soon I'd drifted back into my lesbian orgy again, and ya know what? They really seemed to have missed me!

"Jack..." somehow Mel was in my dream, and then I awoke, "Jack! C'mon, take this, two aspirin and a glass of tomato juice, works wonders..."

It seemed amazing that she was able to come into the orgy to wake me up, and then I remembered to take my hands away from my eyes. I looked up to see her two beautiful blue eyes looking back at me with a bemused smile on her face. In her right hand were the two pills, and in her left, the glass with a dark red liquid, probably the tomato juice I surmised. Figuring all this out seemed to be very painful for some reason, probably the same reason that the lil' guy with the jackhammer was still going full blast in my head.

I managed to push myself up onto one elbow, but even that seemed dicey, and I was still trying to focus on the offered items in her hand, when she just said, "Oh hell!"

The next thing I knew, my nose was being pinched closed, and then she used my nose as a handle to pull my head back. This caused me to open my mouth to complain, but before I was able to get a sound out, she pushed the aspirins to the back of my throat and poured in some juice behind them. Now she let go of my nose and put her hand under my jaw to close my mouth, forcing me to swallow it all down.

This resulted in a very ugly wrinkled-up face from me as my body tried it's best to turn inside-out, but got a pretty good laugh from Mel, as she asked, "Bitter taste, huh?"

"Yeee-yuk," I responded, "Bitter? That stuff's toxic!"

"Here, drink the rest of this juice," she insisted.

I reluctantly drank down the rest of the tomato juice, and realized she was making a fuss over me, so I really ought to be appreciative of it. She took off her robe and slippers and got back into bed, pulling back the covers to let herself in.

"I hope you're not this nasty every morning when you wake up", she complained, "You still haven't even said good morning to me yet."

Mel tried her best to keep her frown going as I watched her lay down.

"Oh darlin', I'm sorry," I said dramatically, putting the empty glass down on the bedside table, "I don't deserve you... here, lets start over. Ahem..." I cleared my throat to say, "Good morning Melissa, love of my life!"

Mel giggled, and then said, "Good morning Joscelyn!"

At first it didn't register, then she looked down to the piece of lightweight silk and nylon that I had been mindlessly stroking. But now that she had moved the covers back a little, my eyes just about jumped out of my head as the shock hit in three phases...

My initial shock: whatever this is, isn't 'on' the bed, it's 'on' me!

Then the full shock: I was wearing a pink baby doll nightie, with matching panties. I sat up with a start as I realized what I had been sleeping in, but then looked at Mel and realized what name she had called me.

For my final shock: she said Joscelyn. How would she know that name? No one knew the name I used for myself when I was 'en femme'. I didn't think that I'd ever told a living soul, so how did she know?

Oh God, there was that damned little man... pounding on metal in my head again, I shut my eyes and brought my hands up to hold on to my head as I was pretty sure this must be a dream and all of it would be gone shortly.

"Awww," Mel chided, "C'mon baby, you'll feel better soon."

I gave up on any chance that this might be a dream, and instead went to full blown panic mode, saying, "Oh God honey, I'm so sorry, what have I done? I can't remember anything after leaving the restaurant last night. Sometimes after I drink too much, I black out, and then it's almost like I'm sleepwalking after that," I explained, talking way too fast, "A-And I'm... I'm not sure... did we... this is Andy's house, right?"

Mel was now looking quite entertained, she moved up to a sitting position against the headboard of the bed with her arms folded in front of her, I now also noticed that her nightie was similar to mine, only hers was black. Mel's smile was confusing to me, she seemed to be taking all of this like it was routine. Like it was totally normal to be in bed with your boyfriend while he's wearing women's lingerie.

"Yes sweetie, this is Andy's sister's old room, I think she moved out after she graduated from college, so Andy put us in here for the weekend," she explained.

Once she saw that I was calmer, she continued, "You really don't remember anything from last night? Hmm, maybe that's why I got the introduction to Joscelyn, I guess once you black out then your 'alter ego' seems to take control, huh? Oh and honey, there's nothing for you to be sorry about," she said as she went to hold my hands in hers, "you were wonderful last night, or perhaps I should say, Joscelyn was... but in either case I loved everything we did together."

"But Mel, are you sure about this?" I pleaded, as I looked down at myself, "Doesn't it bother you that your boyfriend wants to wear girls clothes... Aw hell, I've even told you I would actually rather BE a woman! And none of that... um, upsets you?"

I now stared into Mel's pale blue orbs and I seemed to become absorbed by them, they were coming closer, and closer, and then her lips were touching mine, she kissed me so very softly and whispered, "I-I um... Actually, it turns me on... God, just thinking about you as Joscelyn gets me SO hot baby!"

Mel's eyes dropped suddenly, breaking my trance, and her voice dropped away as well as she said, "I guess that makes me a little strange."

Touching her face as tenderly as I could, I brought those beautiful teary eyes back up to mine and replied, "No, to me you're not strange at all. It makes you something very special darlin', more special than anyone I've ever known."

If there had been anything flammable between us, it would have been vaporized, there was that much heat coming from our eyes for each other. Her hands went under the top of my nightie and tweaked my nipples, which made me grab the back of her neck and kiss her with all my might, forcing my tongue into her mouth. Not so much a normal kiss as an all out rape of her mouth by my tongue! But even as sex crazed as we were, I knew she needed to be 'warmed up' before I could do what I wanted to do next.

But now suddenly everything was easier, Mel's hangover special had actually worked! The little man with the big jackhammer was no longer loose inside my head!

I flipped around for a quick '69' session. Once again I was right in front of that incredible musky aroma that was Mel's beautiful pussy. After pulling her panties down, I used my tongue to gently lathe all around her labia, my right hand fingers flicked her clit, while the left, after getting them nice and wet from her pussy, wandered back to her bung hole. After invading her back door with a lubricated index finger, along with a few minutes of fellatio, Mel was literally thrashing beneath me. She pulled my panties aside and was attempting to suck my hard cock directly over her head, but I wasn't giving her much of a chance to concentrate on it, or anything else for that matter, mostly it was acting as a mouth gag, which was probably a good thing, otherwise the entire house would have heard her yelps, and wild moaning.

But now that I felt she was ready, I could only hope no one was trying to sleep-in this morning, because this... was gonna get loud! I removed my cock from her mouth with a very audible pop. I then quickly flipped back around, and kneeled between her legs, taking a few moments to yank my pink panties down and liberate my raging hard on, then I glanced down at her with the most lustful grin I could manage.

Flipping her over onto her stomach and pulling her legs together allowed me to slip off her black panties, and then I pushed her legs back down so they would straddle my thighs. I sat back onto my ankles from my kneeling position, then grabbed Mel's midriff and pulled her slowly up my thighs towards my cock. I paused for a moment to draw out the anticipation a little. Mel glanced back and let out a small whine, her eyes pleading with me to just start with the fucking!

I took a sharp inhale, yanking her wet pussy up, and onto my straining cock. Instead of a yelp, Mel gave a gut-wrenching scream as she was impaled while at her highest state of arousal. I did not pause for a millisecond before starting a push-pull machine-like action; fucking her with as much passion as I'd ever had before in my life.

"Fuck me Joscelyn... Ooohh yeessss baby... fuck me, you bitch!" she exclaimed.

Wearing this transparent pink silk and nylon nightie, and watching it move and flow around me as we pushed back and forth, her soft blond curls bouncing on her black nightie as well as my own blond locks bouncing in time with hers, and then the guttural expressions coming from Mel that were being directed at her female lover Joscelyn... which was me! All of these were conspiring to make me cum prematurely. I knew I wasn't going to last long, but I was determined to see her to orgasm!

I moved my hands from her midriff, up to under her shoulders, and pulled her up to me, so her back was up against my chest. By using one hand to hold her, I could use the other to massage and tweak her breasts. By this time I was grunting on every push, an almost animalistic sound that she could feel directly in her chest. I was also licking and nipping at her neck as it came into range.

I could tell her breathing was shallower and quicker, and her vocalization had more 'e's than 'o's which were how I could tell that Mel was close to her climax. As I'd done before, I grabbed around her torso and arms together, and sped up my thrusts. But as she started her first orgasm, my mind went inward, my eyesight dwindled to not much more than a pinhole, and then we both screamed. I was determined to continue my motion as long as possible to give her secondary orgasms, but I'm not sure how well I did, as I apparently passed out, with Mel following closely behind. I fell off to her side with one arm and one leg entwined with hers.

As I had feared, the rest of the house had heard our primal screams. Andy and Cindy decided that since we didn't answer when they knocked, that they better see if we were still alive. Walking in, they found two blond-haired lovers sleeping peacefully side by side, one in black, and one in a pink, baby doll nightie. Eventually they managed to wake us up, much to my embarrassment. Cindy, very nicely, threw covers up over us, which gave us, well at least me, a small level of dignity.

"Well, good morning you two," Andy laughed, "Mel I know, but who is this beauty?"

I realized they were looking at me as I very much wanted to dig a hole into the mattress, when Mel said, "Andy... Cindy... I would like you to meet, Joscelyn!"

"And how's Joscelyn feeling this morning?" Cindy pried.

"Apparently Joscelyn was a very bad girl last night," I replied blinking my eyes, "She should have kept herself in the closet until she was ready for the world to see her."

"Oh, I can't blame her, closet's are so stuffy," Cindy said dismissively, "but where did she... er, I mean you, and Mel, find those nighties?"

"Oh, I found these on the bathroom door," Mel said, "I jokingly said to Jack, 'hey, why don't you sleep in this' and threw the pink one over to him. When I came out of the bathroom wearing the black one... Well, there was Joscelyn, all decked out in pink!"

"Wow... if I'd known it would turn him into Joscelyn, I would have thrown some women's lingerie at him months ago", Andy quipped, then got serious, "Oh yeah guys, Dolores, our cook, will only be here until noon, so if you want breakfast, you better get going. And Jack... er, I mean Joscelyn, I want you especially to meet Dolores and talk with her before she goes, she has a lot of information you may find useful."

"Alright then? We'll get dressed and meet you downstairs," Andy said as he left.

Suddenly I realized that I still had a couple important questions for him, but he was already out the door and walking down the hall towards his bedroom. Throwing the covers off and jumping out of bed, I hit the floor running.

I had only gotten down the hall a few feet when suddenly Dolores came from around the corner and I ran right into her. I froze in my tracks, while she covered her mouth to stifle a giggle, before she said, "I was just going to wake Andy, and let him know that he needn't hurry, as my plans have changed and I don't need to leave early today. But as long as we've run into each other... well, now you know too."

My face became hot with embarrassment as I then remembered what I was wearing, and gradually began stepping backwards toward the bedroom I came out of, while stuttering, "Oh... I was just going to, ah... I'll let Melissa know!" and ducked back into the doorway, but before I could close it, I heard Dolores giggle outright.

After shutting the door, I just stood there for a few seconds with my eyes closed and my back leaning up against it, wondering how all of this had come to pass. But when I slowly opened my eyes, I saw a beautiful blond in a black baby doll nightie, smoldering on the bed and curling an index finger into a come hither signal that could have only one meaning, and all other thoughts faded to insignificance. Well, Dolores did say we had plenty of time to come downstairs for breakfast...

I slowly walked to the bed and sat down, then stretched out my hand and waited. Mel gave me a puzzled smile, but decided to play along and put her hand into mine. I kissed the top of her hand softly, and said, "Would m'lady do me the great honor of allowing a lowly handmaiden to bath her on this fine and lovely morning?"

At this point I already knew how Mel reacted to all the usual forms of lovemaking. Now I thought I would see just how much of an effect my favorites had on her, romance and role-play. I think I hit a hot button, as I heard her gasp with a sharp intake of air.

She replied with, "Why Joscelyn... the honor is all mine I'm sure," Then I quickly flipped her hand over and began licking her palm, and heard another sharp gasp, as I took a quick look down at her crotch in time to see a wet patch appear at the front of her panties. Well, she sure didn't hate it anyway!

I got up off of the bed slowly pulling her along with me, and as she reached the edge of the bed, I leaned down and picked her up and carried her into the bathroom. Once inside, I flipped on the lights, and carefully placed her on a countertop across from the shower stall. As she watched, I untied the bow of my nightie and pulled it over my head, then placed it on the counter next to her. Then I took off the panties and put them there as well, and turned to the shower, leaned in and turned on the water. Now totally naked, I indicated that it was her turn by untying her bow. She pulled her nightie over her head and placed it next to mine, then took off her panties as well. After checking the water temperature, I stepped into the shower and offered her my hand to help her in. She reached across and grabbed my hand laughing, then jumped off of the counter rushing headlong into my arms in the shower.

Water is so erotic... both of us were getting turned on again, so I said, "Turn around, and let me start on your back."

The shower was running down her front, and that gorgeous ass was right in front of me now. As I reached over for the soap, my chest momentarily pressed into Mel's back. I rubbed my hands together and began to rub the lather onto her shoulders.

"Mmmm that feels so good," she moaned.

For me too, it felt truly wonderful to touch her soft shoulders and smooth skin! I rubbed her back with the soapy water, starting at her shoulders and working my way down. I got to the small of her back, and couldn't resist caressing Mel's ass with my wet hands. Another moan escaped her lips. I continued to rub with both hands, giving ample attention to that pretty little behind. Each time I touched it, she moaned again. Her hips were swaying and her own hands were now rubbing her vagina.

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byJoscelyn2tg© 10 comments/ 27832 views/ 15 favorites

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