Chapter 4: Shopping

Chapter 4: Shopping

When I woke up the next day, light was streaming in through the window and the clock read 9:25. I also quickly noticed that I was alone in the bed. Looking around I saw my phone sitting on the nightstand next to me. Ben and I had agreed to leave phones behind for our trip, a sort of “off the grid” adventure. That and there was no cell service out in those woods anyway. I had left my phone put away in a drawer for safe keeping, but it seems Olivia had moved it here for some reason.

Picking it up I can see she’s sent me a message, “Gone out to pick up a few necessities. Be back around noon. XOXO” So that solves the mystery of why I’m alone. Pulling the covers off of me I once again feel the unwelcome and painfully acute sensation of fabric rubbing over my dickhead. Looking down at the head of my cock it seems I’ve recovered from the sandpapering my jeans gave me yesterday, the redness having disappeared. The oversensitivity of the sheets on my cock seems to just be oversensitivity from too much direct stimulation. I really hope my new dickhead can adapt as fast as I did after my circumcision. It was weeks of **** then, and this seems worse.

Standing up out of bed caused my bladder to start making some demands for my attention. I walked into the bathroom and stood in front of the toilet. As I lifted the seat I remembered the incident in the hospital bathroom. I really didn’t want to be cleaning up piss off the floor again. So I lowered the seat back down and decided to sit down on the toilet. I angled my hips and pressed down on my dicklet before I released the stream. I certainly didn’t feel dignified or manly sitting down to piss, but at least everything ended up in the bowl.

After all of that time in the hospital I’d been missing a real shower. There’s no time like the present so I grabbed a towel for after and hopped under the relaxing warm water. I scrubbed my body and slowly got a closer look at each limb one by one. I hadn’t been spending the time in the gym that I should have so my muscles weren’t as defined as they once were, but before the cave I still had some definition and didn’t look bad without a shirt. My arms had never looked like those on the muscle heads at the gym, but flexing my biceps had been known to cause Olivia to make some appreciative noises. Now my arms were undefined twigs with only the barest hint of muscle anywhere on them. Even my shoulders seemed less broad than they had been.

Moving a little lower I soaped up my legs. I had never been one to skip leg day, and had ended up with a well-developed lower half. My thighs had always been rather substantial, and they still were but for wholly different reasons. From the knees down my legs had become thin little sticks leading up to soft thighs that expanded into my larger ass. Speaking of which, I’ve always had a nice ass, as Olivia like to point out, it was always well muscled and somewhat prominent. Now, in absolute terms, my ass was probably about the same size it used to be, but on my new smaller frame it looked gigantic. I could feel the strong muscular core as I lathered up my cheeks, but it was now covered in a soft layer of fat making the whole thing quite enticing. Truthfully it’s the exact kind of an ass I like in a woman, I just never thought I’d have one like it attached to me.

Moving back to my upper body I continued soaping up my chest. At one point in my life I’d had six-pack abs. Those times were a few years behind me, and I’d even started developing a bit of pudge around my midsection. Now both the muscles and the fat were gone. My entire chest was shapeless, I didn’t so much have pecs, as I did have nipples in the middle of my smooth chest. And when I say smooth, I mean smooth. After my thorough investigation I can say for sure that I don’t have any body hair below my eyebrows. None on my arms, legs, chest, or anywhere else I could find. I haven’t needed to shave my face since waking up at the hospital and I don’t think anyone was doing it for me when I was **** for those weeks either. I guess that’s convenient in its own way, but certainly doesn’t do anything to make me feel manlier.

Finally I move onto the last part of my body that I’ve been avoiding up until now, my tiny dick. It’s still been weeks since I last got off and just the gentle trickle of the soap and water running down my body before cascading off my little nub and down to the drain has been enough to stimulate me to hardness. Reaching a hand down I rubbed soap over my diminished scrotum, needing a much smaller motion to encompass the whole thing than ever before. I could feel my small grape sized testicles within, shifting inside my much reduced ballsack. I used to have some pretty hefty balls, around the size of a pair of ping pong balls, now they were lost in the folds of even the tiny flap of skin my scrotum had become.

Even these small ministrations were enough to **** an involuntary moan of need from my mouth. Not being able to hold back any longer I moved my soapy fingers upwards toward my cock which was even now throbbing with need. Before my circumcision I used to grab the skin near the middle of the shaft and pull it back along my full length allowing the foreskin to slide back stimulating and uncovering the head. Then on the upstroke I’d push the skin forward causing the foreskin to re-cover the head before my fingers eventually reached the head itself stimulating it through its skin covering. Once I got cut I had to completely re-learn how to masturbate. Ever since my circumcision I’d needed lube in order to jerk off my old big dick, and the soap on my fingers will have to do for my new reduced one. Before I’d start near the bottom of my shaft and allow my lubricated fingers to slide along the taught skin of my shaft until just behind the head, focusing on the length past my circ scar. Direct stimulation to the head was simply too much, but working the shaft and remaining inner foreskin was enough to get me over the finish-line.

Looking down at my new cock I realized I was going to need to re-learn how to jerk-off once more. Before, a lot of my technique focused on the shaft. Now I basically don’t have one, even fully hard as I was now, the shaft was less than an inch long attaching my inch long cock head to my hairless groin. There wasn’t even enough room to get two fingers between my head and my body, let alone room to stroke it. The only option I could see was going to involve stroking the head. I used my soapy two fingers and thumb to caress my dick head attempting to get it clean before I got down to figuring out a new stroke technique. That alone was enough to buckle my knees and **** a needy moan from my throat. I was barely able to keep my knees from slamming into the floor of the shower before I regained control of my muscles and stood upright once again. Pleasure shot through my body overwhelming all of my senses, it only took a tiny motion and I was seeing stars. It was like every nerve ending of my old 7 inches had been compressed and concentrated into my new 1.5. It made everything more intense than I’d ever felt before.

Breathing heavily and leaning against the shower wall, my need drove me back to stroking myself. Now braced against the solid wall I was able to keep my legs under me as I did my best to pleasure myself. Being **** to use only two fingers caused an unwelcome comparison forcing me to admit my new technique was closer to stroking a clit than to actually jacking off. Fighting through this uncomfortable realization I continued stroking. As I slid my fingers over my glans I was only able to get in a few motions before the sensations flashed over from exquisite pleasure into debilitating pain and oversensitivity.

A few times with Olivia she’d continued to stimulate me after I’d just cum, grinding the head into the palm of her hand. Another time, continuing to suck the head of my dick after I’d finished. Both times resulted in overwhelming pain that left me twitching helplessly trying to escape the unwelcome overpowering sensations. Once, I’d gotten her off and refused to stop sucking her clit until she too was twitching uncomfortably, showing exactly what it was like. She quickly learned that my “adorable” convulsions were not so pleasant, and something she could be victim to as well. Her little routine rapidly stopped.

I once again found myself subject to the same sensation. The sensitivity of my cock-head turned almost immediately into oversensitivity. Simultaneously the nerves of my cock were begging me to stop, but my need to get off drove me to continue. Quickly the muscles in my legs did give out and I crumpled into the bottom of the shower unable to remain standing. Even then I couldn’t tear my hand away from my crotch still rubbing as fast as I could. Soon the spasms travelled to my arms and I couldn’t keep my stroking coordinated enough to keep my fingers touching my cock. At this point I was **** to admit defeat, letting my hand drop to the wet floor of the shower even as the water continued to pound against my body. I lay there panting and not moving as my heart felt like it was going to pound out of my chest. My cock was still throbbing between my legs like a solid little bump, but I was light headed feeling like I’d just run a marathon and I still wasn’t even close to orgasm.

Once I was able to stand up I tried to get off twice more, but both times I ended up twitching on the ground, no closer to orgasm. Eventually the water started to run cold and I was **** to admit defeat and get out of the shower. The conventional wisdom of a cold shower seems to be true. The freezing pounding water cooled down my ardor, but didn’t completely extinguish my desire. I’d gone back to flaccidity, but a big part of me still wanted to get off. Horrifyingly enough for the first time in my life, I wasn’t sure how I was going to accomplish that. For my entire life, as long as I’d known what an orgasm was, I was able to get off masturbating and now it seemed that was impossible. As I was drying off and trying to warm up, while mulling over my new realization, I heard keys opening the door of the apartment and Olivia calling out as she closed the door behind her.

“Kyle, I’m home. Are you up?”

“In here.” I called from inside the bathroom. Looking around I realized I hadn’t brought any clothes in here with me and I’d need to walk out in front of Olivia naked. For the first time in my life I was filled with shame at the prospect of being naked in front of the woman I loved. Consciously I knew she’d already seen what I look like naked now, but even so a part of me wanted to hide my new shameful appearance from her. Wrapping myself in a towel as best I could I walked out into the bedroom where Olivia now stood rifling through some bags she’d set down on the bed.

Turning to look back over her shoulder at me she said, “I bought you some things.” before reaching inside a bag to pull out a small scrap of cloth. Handing it to me I realized they were a pair of white underwear. “I wasn’t sure what would fit you best now so I got you a few different styles and sizes” she said gesturing back to the remaining bags on the bed. Indicating the pair in my hands now she said, “You mentioned having sensitivity problems and I know that after your operation tight briefs helped, so I stuck to those mostly. These are men’s smalls.” Seeing my hesitation she felt the need to prompt me, “Go ahead, try them on.”

I still wasn’t feeling great about dropping my towel, but really I had ****. I pulled off my towel and stepped into the new pair of briefs. Pulling them up my legs I could see that these weren’t going to work. They fit over my new ass pretty well but the waistband didn’t even come close to fitting. Had I let go of them they would have fallen off almost immediately.

“I was afraid of that,” Olivia said scowling down at my waist. “Here try these,” she said handing me a new burgundy pair, “these are a boys’ large.”

I wasn’t overjoyed at the idea of wearing boys’ underwear, but clearly the men’s underwear was no longer going to work. With little other choice I slipped on this new pair. These were better, but still not great. Once I had them on I could see that the waist was still a little big, with the elastic not even taut with room for a couple of fingers between. However these were getting a little bit tight over my expanded rear end. Looking down at myself for a moment I look back up and Olivia and give her my opinion, “These can work, they’ll stay up at the very least, but they’re a little big in some areas and a little small in others.”

“Ok well I also got the mediums, would you like to try those?” she said holding out a green pair.

Trying these on, I see that I’m going to have different problems. Once I have them pulled up the waist fits perfectly, enough stretch to hold them on firmly but not so much as to be tight. The tightness came just below that, my ample bottom pressing out the back and stretching them uncomfortable over my legs. Where the larges were tight but bearable, I could see these beginning to cut off blood flow within short order. Depressingly, looking at the crotch area in the front I could see that it was the one area that wasn’t tight. The idea that I had a smaller dick than clothing designers thought a boys’ medium should have was more than a little hard to take. But the baggy surplus of cloth bunched up over my dick didn’t lie, my cock was smaller than that of a child. With some strain I pull these off of my legs before handing them back to Olivia saying, “I don’t think those are going to work. I guess I’m stuck with the larges. They weren’t great, but at least they’ll stay up.”

I put the mediums down before grabbing the larges and sliding them back on. Looking at myself I’m back to the same problem. The waist is a little loose and the ass is a little tight, but it’s at least workable. The biggest issue is again the crotch, these are even looser than the last pair. I guess I can’t really expect underwear made for someone with a halfway normal sized dick to fit me even if I was hoping for tight underwear. Even now I can feel the bunched up cloth starting to aggravate my dick head. But commando was worse so I guess I’ll just have to grin and bear it.

Looking up I can see Olivia chewing on her lip looking a little distracted. Noticing my gaze she hesitates for a moment before saying, “I’ve got one more idea, try these on,” as she handed me a new set of blue cloth. Holding them up I see these are styled more like a pair of boxer briefs, than the regular briefs I’d tried so far. I’m not optimistic, but I’m willing to give them a try.

Sliding these on the difference is immediately apparent. They’re tighter overall but stretch enough that they’re tight in the right places without being too tight. Pulling them up all the way they fit perfectly around my waist and hugged the curve of my ass. The most surprising part was the groin area. The cloth curved in perfectly holding my dick down with just enough **** that it was tight enough to hold everything in place to prevent rubbing, but not so tight to be uncomfortable. The little bump my dick formed in the fabric wasn’t particularly flattering to my ego, but it basically solved my sensitivity in clothing problem. My initial relief at finding the apparently perfect pair of underwear was quickly overcome by a sudden realization. There’s no way these would fit anyone with a dick. “What style did you say these were?” I ask Olivia suspiciously.

“They’re called boyshorts,” speaking slowly with some hesitation she continued, “they’re a style of women’s underwear.” Seeing the look on my face, which full of shame and unhappiness, she started talking rapidly. “I know, I know, they’re women’s clothes, but you needed tight underwear and with your new… situation and I didn’t think the other ones would be tight enough, but I shouldn’t have just sprung this on you. You don’t have to wear them, we can switch back to one of the others, whatever you-“

“They’re by far the best choice, you were right,” I interrupted. “Thank you, these are perfect, they’re exactly what I needed. I can’t say I’m happy about wearing panties, but I’m going to have to make some changes going forward. I’m glad you thought of this, I never would have, and I would have suffered in the other kind.” I said trying to reassure her, and by the look on her face I could see she was feeling relieved she hadn’t offended me by buying me women’s underclothes.

“Ok, well now we’ve settled the underwear we’ve got to get you the rest of a wardrobe. Throw on Ben’s old clothes, for the last time, and I’ll take you down to the mall to get some stuff that actually fits. We can get you more underwear too, in whatever style you want.” She said pulling out and handing me the rest of the pack of boyshorts, letting me see the packaging for the first time. They were emblazoned with women wearing the underwear I had on now, and they didn’t look all that different than my lower half did at this point. Looking down at myself I realized sadly that the little bump in my underwear could be mistaken for a woman with an unusually large clit poking out rather than a penis. Rather than dwelling on that horrifying realization, I got busy slipping on Ben’s ill-fitting clothing while Olivia packed up and put away the remaining bags of underwear. I was really starting to miss being uncut, instead of pulling my foreskin forward to protect my glans I was now wearing women’s underwear.

Once I was fully dressed and Olivia had finished her preparations we headed out for our shopping trip. We went down to the department store in a relatively nearby mall. Olivia suggested that we could pick up most things there and it would be faster than going to a bunch of specialized stores. She planned to take me to her tailor later and get me some custom designed clothing for my new stature, but that would take some time for delivery and I needed something to wear now.

The department store was beyond humiliating. Consciously I know that no one was really watching or paying attention to what we were doing, but it still felt like everyone I walked past couldn’t stop staring at the tiny freak I’d become. This was my first trip out in public since my reduction in stature and walking past all of these people was a surreal experience. I used to be taller than most men, now I’m shorter than three quarters of the women we walked past.

The shopping itself was even worse. I mainly stayed in the dressing room and Olivia brought clothes to me to try on. We started with the men’s department. Not a single thing fit me. We went from men’s small, to boys’ extra-large, and then to boys’ large before we found a shirt that didn’t look ridiculous. Hell, I could have probably gotten away with a medium, but I wasn’t in the mood for that kind of humiliation.

Pants were even worse. We followed a similar pattern, starting with men’s smalls before realizing that was hopeless. They didn’t come close to fitting around my waist and only held on for a moment before falling off of my expanded bottom and hitting the floor. So we progressed to boys’ sizes and encountered a new problem. Boys’ large pants were loose, but workable around my waist, but they were very constricting around the expansive globes of my new ass cheeks. Any fabric tight enough not to bulge noticeably out the back looked practically painted on. I could wear them, but I could tell within a few hours of wearing them I’d be in huge discomfort.

Seeing this disappointing result Olivia had an idea. She wouldn’t tell me what she was bringing back, just to “keep an open mind”. She brought back a few pairs of jeans, which did seem much more accommodating of my new rear end. It took three pairs before she found the perfect size, which both fit in the waist and wasn’t too tight around my new hips and ass. It took a little prodding but eventually I got Olivia to admit my new pants were from the women’s department. As much as I hated to admit it I knew these were the only things that had come to close to fitting if I hoped to look decent in public.

Altogether we bought several shirts, mainly t-shirts but a few long sleeves and other styles. Shopping in the boys’ department meant most had childish designs on them so I had to restrict our selections to flat colors without designs. We got several pairs of women’s jeans, which I carefully inspected to make sure they were as gender neutral in appearance as possible. We also got a few pairs of shorts and sweatpants from the boys’ department. The stretchier material means they won’t be appropriate in public, but they’ll be comfortable around home. That and I refuse to go to the women’s department for loungewear.

With that out of the way I now had a basic wardrobe so I could go about regular daily activities. Olivia still insisted on dragging me along to her tailor that afternoon so she could get me a few more things. I wasn’t going to be finding off the rack dress clothes anymore, for example. The man was professional about the whole thing and took my measurements quickly. By this point I had basically checked out mentally. As much as I didn’t want to admit it this whole day was pretty traumatizing. I was walking around in public in women’s pants and underwear now, which was a pretty concrete lesson on how my life is never going to be like it used to be. As it was, I had no interest in the dimensions of my new body and tried very hard not to listen as the tailor measured me and wrote it all down.

Once that was over he and Olivia talked for a long time about the types of clothes she had planned to be made. I stood there nodding when they looked to me for an opinion, but I wasn’t really listening to anything they were saying. I was mainly focused on not freaking out about everything that had happened to me. Up to this point it was easy to pretend that this was all some sort of dream. I’d wake up, or a doctor would come by with a genius idea to put me back to normal. Spending a day buying clothes really drove home that this is permanent, there’s no going back to my old life.

Eventually Olivia finished the discussion with the tailor and we were able to leave. I think she realized I was feeling a little bit out of it and did her best to cheer me up. This whole process had brought us to early evening and so at her suggestion we went out to eat at one of my favorite restaurants. The evening had me feeling a little bit more like myself, and I enjoyed a night of great food and great conversation with the woman I love.

Walking back into our apartment Olivia pulled me by the hand toward our bedroom with some serious come-hither eyes. “You know it’s been a few weeks since either of us has had sex. I thought maybe we could fix that tonight.” I could hear the need thick in her voice.

“Olivia, I’m not so sure about this-“

“Well then it’s good that I’m sure.”

“I’m not the same guy I was before. I can’t, I can’t do the things I used to… in bed. I can’t expect you to-“

“Don’t,” she said reaching down to wipe a tear off of my face. I didn’t even realize I was crying. “Don’t tell me what I want. I love you and I want to be with you. You, not the body you used to have. I understand that things are going to be… different going forward, but as long as you’re willing to work with me, I’m with you no matter what.”

“I love you so much.” I said wiping away the remaining tears before she leaned down and we kissed.

“I love you too,” she said before continuing with a smirk, “now take off your pants I’m still horny.”

We both stripped naked in record time. I tried to keep my courage after Olivia’s little pep talk, but pulling off the women’s underwear I was wearing made it a little difficult. Even so, once exposed my tiny cock was rock hard throbbing with need. It certainly helped that Olivia stood there naked looking as good as she ever has.

Her long black hair cascaded down over her back in beautiful waves, pulled back from her face exposing emerald eyes that absorbed the details of my body. Her sharp cheekbones painted with a blush of red arousal as she bit the right corner of her full lips. Tracing my eyes down her body I lingered on her full perky breasts, nipples rock hard. Her breasts were the perfect size, just big enough for a solid handful. Of course that was before my hands became considerably smaller, now I suppose they’ll be larger than my much smaller handful. Flowing further down my eyes passed over her svelte abdomen, taut with muscle sculpted by her corporate gym. As I continued my visual journey I went to her broad hips flaring out before gently curving down to her long legs. Framed in the center of her groin were the delicate lips of her pussy flushed and swollen with arousal, even now carefully maintained to hairlessness.

I advanced upon her gently pressing her backwards towards the bed as I kissed her neck. I reach up and gently caressed her, from my perspective, larger breasts as she lowered herself to the bed. I crawled onto the bed on my hands and knees, never allowing my lips to leave her flesh. I slowly worked my way down her body kissing over her chest, lingering on her engorged nipples for a moment, before continuing over her tight stomach. Olivia was moaning in pleasure with the sensation of my lips upon her skin, it was clear she really needed this too, and this was before I’d even made my way to her womanhood.

Finally my journey came to an end between her legs where I carefully sucked each of her inner labia between my lips one by one. I gently tongued the opening of her vagina, tasting the rush of fluids that even now flowed freely from her core. I moved back up and gently danced my tongue over her clit pushing the hood back before sucking the delicate pearl itself between my lips. I spent minutes lavishing pleasure upon the most sensitive parts of her anatomy, alternating the sensations and focus of my motions to keep her moving towards the edge. It wasn’t long before I felt her hands against the back of my head pressing me powerfully into her molten depths. Soon I felt her legs squeezing the size of head as her muscles trembled helplessly in orgasm as she cried out in bliss.

I rolled off of her and laid on my back on the bed as both of us panted with exertion and arousal. Once her breathing had begun to normalize Olivia turned to me and said, “Now it’s your turn.” As she reached towards the rock hard nub between my legs. She gave it a few strokes that filled me with bliss, but before I came even close to my peak I once again flashed to oversensitivity. It was too much stimulation directly to the head, but all I really had down there was the head. Involuntarily my legs closed and I pushed her hand away.

Between pants I was able to get out the words, “I’m not sure I’m ready for that yet.” I could see from the look on her face that she was a little bit hurt and somewhat confused by my reaction.

“You made me feel so good, I just wanted to return the favor.”

“I understand that, but I’ve got some stuff I need to work through. I’m not sure I’m ready for you to get so intimately acquainted with my new nubbin. I’ve still got to get used to it.”

“Well if you’re sure.” She said sounding uncertain.

“I’m just glad that I could get you off. It goes a long way towards making me feel like a real man again.”

“You’re not just a man, you’re my man, and a damn fine one,” she said crawling up on the bed and kissing me on the lips. “I’m ready to wait as long as it takes for you to be ready. Especially if you keep working that magic tongue and giving me orgasms like that!” she giggled.

“You’ve got it!” I said wiggling my tongue in the open before kissing her back. With that we prepared for bed before we snuggled together and drifted off to sleep in each other’s arms.