Sandy's Journey

By J J

Published on Apr 13, 2024

Transgender

CHAPTER 11: Bobbing for Dicks

We swam back into consciousness about 9 the next morning. I can't tell you how pleasant it was waking up in the arms of these two beautiful gurls. Kim and I both wanted to get home and change, but Char held us long enough to get some hot coffee into our bodies. A quick naked breakfast of bagels and coffee sufficed to wake us all up. Char threw on a robe while Kim and I dressed in our clothes from the previous night, and a round of serious kisses at the door almost lured us back into bed.

Kim's car was there, so we said a long, sweet goodbye in the parking lot.

"This has been very quick, but I'm getting quite used to being with you," I said between kisses.

"I know," said Kim, "Me too. Just don't get crazy on me and run away."

"Not today, doll. It's all a big change to me, but you're the kind of light I didn't know I was looking for."

She kissed me again. "Oh, baby," she sighed. "I promise not to get crazy on you either. Play it by ear and we'll see where it all goes."

One last kiss, and we each drove off. I can't say I wasn't a little scared at this point. So many changes in such a short time. I had this wonderful new girl, and her world was completely outside my previous experience. Tom and Judy, Kim and Charlotte. I could feel a tingling where I'd been penetrated, and a warmth inside from the acceptance I'd felt. I couldn't stop smiling.

I got back to my place and took a long hot shower, made some lunch and checked my email and the news websites I followed. While I was online I couldn't resist going to one of the clothing sites I'd found that sold lingerie tailored to men. I picked out a babydoll set, something completely out of character for me -- I wasn't the helpless little girl type. Deep inside me there was still a man. Still, I thought Kim might get a kick out of it. No top/bottom hierarchy had been established. We seemed equals, our roles varying by the moment. I also bought some saucier men's underwear -- thong briefs with enough support to keep my junk corralled, in shades of blue and grey.

The girls had given me the address of a store where I was to meet them at 3. They hadn't told me what to wear, so I just threw on boy clothes, jeans and a polo shirt. I checked the route and left in plenty of time to get there on schedule. They had just told me it was "Bob's place" and given me the address, no business name. I was a bit surprised to find it was a thrift store, but it really was named "Bob's Place."

I didn't see Kim or her car nearby, so I just wandered in to look around and wait for them. It was a fairly large building, with all of the used clothes and general junk you usually find. I strolled down the racks of women's clothing. A sheer nightgown caught my attention, and I paused to feel the fabric when I heard a voice behind me.

"No, no, that's not you, Sandy. The good stuff is in the back." I looked behind me and immediately recognized Kim's friend Penny, this time in male form. He was wearing khakis and a button-down long sleeve shirt, all pressed with perfect creases.

"Hello, Sandy," he said. "The girls told me you'd be coming by and asked me to take care of you. Follow me."

I followed him towards the back of the store. "I was sorry I didn't get to spend much time with you last night," He said. "I sort of got swept off my feet at the club." He turned and smiled, then unlocked a door marked PRIVATE -- NO ENTRANCE.

Stepping through, I found myself in a whole other section of women's clothing, but of much better quality. There were racks of dresses, skirts, slacks, jeans, blouses, and lingerie. "I set this up for girls like us," Bob said. "Here you can find things in our sizes, of good quality, and try things on in complete privacy. No one will come back here except other gurls. You'll find anything you need for whatever level of dressing you want to try."

"I'll leave you here. Help yourself. There are dressing rooms and mirrors over in that corner. I'll be back in a while to check on you. If you need any help, press the button near the dressing rooms -- that signals me." He put his hand on my shoulder and added with a grin, "I'm really looking forward to seeing you all pretty."

With that he left me alone, and I heard the lock click after he went out to the front.

The racks were labeled with both women's and men's sizes, which was quite helpful. I really had no idea what women's sizes would fit me. I knew I wasn't ready to dress in public, so I passed by the street clothes and went to the sleepwear and lingerie section.

Oh, my. Such nice things, so very feminine. I picked out a bra and panty set in robins-egg blue. Then there was a pretty black set with just a bare front, no cups. I had a pink set like them at home, but the size on that set wasn't quite right. There were some lovely garter belts -- I'd never tried one of these, always wearing thigh-highs that were supposed to stay up but seldom did. I picked out a couple to match my lingerie sets. In the sleepwear section I found a wonderful green robe. I needed something to wear when I was being femme, and my grey terrycloth robe just didn't do it.

The fitting rooms were large, with great mirrors. I stripped to my skin and tried on the lingerie sets. The men's and women's size tags were right on. The black set seemed to push my ass out, which I was sure would make me popular in any gay club, but the blue set really worked for me. The blue went with my eyes, and the AA cups felt wonderful on my chest. The light color panties really seemed to accentuate the curve of my ass. They really didn't work with the green robe though, so I thought I'd find a second robe to buy. I tied the sash on the robe and tip-toed barefoot out to find another. It only took me a minute to find a longer robe in a better color for the blue. It was kind of sheer, but had great lace details.

I went back into the fitting room and tried everything on. I was amazed that my cock wasn't rock hard from the feel of all this soft fabric. I was glad Kim had sent me here. I kind of wondered where she was, but I was having too much fun to worry about her.

I had stripped naked again and tried on a low-slung red garter belt. It felt so nice on my hips, but I didn't have any red panties to go with it. I wanted to find a pair, so I threw on the green robe and slid out into the main room.

And immediately found Kim, going through the rack I was headed for. Bob stood nearby, his greater height looming above us both. Kim was wearing a sleeveless print blouse over a skirt that was just a bit too short for the office.

"Oh, my," said Bob, and Kim turned to face me and smiled.

"Very nice, babe!" she said. What's under the robe?

"Not much, I'm afraid," I said. "Should I show Penny?"

Kim looked at Bob, who nodded enthusiastically. I took hold of the robe, opened it wide, and slid into a slinky pinup pose I'd seen in an old photo somewhere. My cock flopped back and forth against my thighs before settling. Kim and Bob applauded, I did a slight curtsy and closed the robe again.

"I came out to find panties to go with this garter belt," I said. "Would you care to help me look?"

Bob held put a hand. "I've got just the thing. Stand right there." He looked me up and down for a moment, gauging my size, then went to the lingerie racks, returning with a red bra and panty set. "These were made to go with that garter belt. You try them on while I find you some stockings. I think you're the same size as Kim."

I took them from his hand, then leaned into Kim for a kiss. She responded like we were an old couple who'd been doing this for years. She fit so perfectly against my body.

"Will you do a fashion show for us?" she asked. I kind of blushed and she laughed at me. "I've seen all of you, and Bob will eventually, so go ahead."

I went back into the fitting room and changed into the black set, adding a black garter belt, then put the green robe back on. Kim was sitting in a chair, and I did my best catwalk performance, swaying hips, opening the robe in front of her. "Good choice, babe!" she exclaimed. Then I repeated the performance with the blue set and the blue robe. "I love that!," Kim said. "I can see you right through it. Very sexy!"

I went back in and changed into the full red ensemble Bob had helped me put together. I didn't have a robe to go with it, so I stepped out without one.

"Wow, that is so hot," Kim said. As I posed for her Bob returned with a package of stockings.

"You look quite edible in that, Sandy," Bob said, and Kim giggled. Opening the package, Bob held up a pair of black seamed stockings. "May I do the honors?" he said. There was a chair nearby, and I sat down, my butt near the edge, and put one of my legs out and up. Bob threw one of the stockings over his shoulder. Bunching the other up in his hands, he placed it over my foot and slid it up my leg. He massaged the stocking to get the seam placed correctly.

His soft hands on my thigh, so close to my cock, had an expected effect. Putting my ankle on his shoulder, Bob attached the stocking to the garter belt snaps. Then he grabbed the other leg and repeated the performance. When he finished, I was almost lying in the chair, my ankles over Bob's shoulders, and he was caressing my legs. His gaze shifted from my eyes down to where my cock was stretching the front of the panties.

"I don't know what you think, but this feels wonderful to me," he said. "This is the brand I usually wear when I want to get fucked hard."

"There's an idea," I almost whispered, and smiled up at him. Bob dropped my legs and I put my stockinged feet back on the floor and spread my legs. I looked over at Kim, who smiled at me and nodded. Her hand was between her legs, rubbing her crotch. I guessed this had been the plan, and decided to just go with it. The girls had alluded to Bob's giant cock, and I wanted to find out for myself.

There was already a large bulge visible in Bob's khakis, and I leaned forward and placed my hand on it. Oh, yes, it was definitely bigger than mine or even Tom's. I opened my mouth and placed it against the bulge, breathing out hot air through the fabric onto his rod. A stripper had done that to me once, and I almost came in my pants. It had the desired affect on Bob, and he moaned.

I undid his belt, pulled down his zipper, and let his pants fall around his ankles. Underneath I found hot pink panties, with a thick long cock pushing out over the top. Reaching around and grabbing his ass with both hands, I pulled him against my face. I repeated the trick of breathing hot air through the fabric, starting down near his balls and moving slowly up to the exposed head, which I kissed repeatedly. Putting my hands in the waistband, I pulled his panties down over his hard cock and let them fall down to his bunched trousers. He stepped out of all of it and kicked it to the side.

I reached down and held his balls with one hand, grabbed his cock shaft with the other, and went to wor stuffing it into my mouth. It had to be 8, maybe 9 inches long, and thick, at least 2 inches across. I took the whole head into my mouth, and could only accommodate a few inches more. The tip hit the back of my throat, but getting it into that opening would take a lot more practice than I'd had. I took it out of my mouth and honored it with kisses, then licked all the way around before sucking it back in. I fucked it with my mouth, taking all I could, and matched my mouth with strokes of my hands. His balls were equally big, and all of him was shaved bare. I could smell a little bit of lotion on it. Everything I felt was wonderful.

I felt a pair of hands on my shoulders. Kim had stood and pressed herself against Bob from behind, reaching around to encourage me. "Suck that big cock, baby," she said, "You look so sexy dressed like that with a big prick in your mouth.

I felt so sexy. I felt like a slut, really, but one of a community of sluts. I could picture Kim or Charlotte or Penny doing exactly the same thing, so I was quite comfortable.

Bob unbuttoned his shirt and tossed it aside, revealing a bra that perfectly matched his panties. Penny, I thought, he's Penny now. Call her that.

"Penny," I said, "I love this cock. I want to suck it for a while, but if there are other things you have in mind, I'm easy." I felt easy. I felt like one of those cum dumps I'd seen in porn films. My asshole twitched, asking for cock and wondering if this one would fit.

Behind Penny, Kim unzipped her skirt and let it fall to the floor, kicking it over to the pile Penny had started. She dropped her panties and kicked them over as well. She stuck her cock between Penny's thighs, and I began to stroke it in time with my mouth on Penny's gigantic prick. I was too busy to remove my own, but the soft fabric rubbing against it felt wonderful. I'd have to buy this set now, because I could feel an increasingly wet spot of precum on the front of them.

My cock work was having the desired effect. Both Penny and Kim moaned softly as I stroked them. I used saliva to wet my hand for sliding up and down on Penny. Kim's cock gave me a few drops of precum that I rubbed around the head. Kim's hands went to my head, holding the sides and forcing me to take every inch I could fit. She increased my speed, fucking Penny's big rod with my mouth.

Then Kim came around next to me. With one hand she held Penny's ass. The other went over mine on Penny's cock, and we masturbated her together.

"What do you think, Sandy?" she whispered to me. "Do you want to try it? It's okay if you don't feel ready."

I did have to think for a minute. Penny was bigger than anything that had been inside me before. I'd look like one of those gape videos I'd seen online.

"It really is okay, honey," Penny added. "I don't want to hurt you."

I came to a decision. "Let Kim go first and open me up, and we'll see what I can do then," I told them.

I disengaged from Penny's cock and stood up. Kim came into my arms and we kissed for a bit while Penny bent her knees and rubbed her cock between my thighs. Then I felt Penny move away. Kim eased me over to the chair, where I knelt on the seat cushion, my elbows on the back. She moved in front of me and I took her cock in my mouth. It tasted wonderful, and I'd had enough of it that it was familiar and comforting.

Penny came up behind me, and I felt her hand between my cheeks, spreading lube over my hole, then pressing it inside. Penny's hands were larger too, and two of her fingers slipping into my boy pussy were almost as large as Kim's cock. Penny fingered me for a few minutes, then my two fuckers switched places. Kim slipped easily past my stretched sphincter, and in one long slow movement penetrated me completely, until I felt her hips against my ass. Penny's large cock went back inside my mouth. Bent over I could take a little bit more into my mouth, but I still needed my hand to encompass the whole length.

Kim moaned softly behind me. "Sandy, you have the best pussy ever," she whispered, her voice husky as she fucked in and out. Penny's hands caressed my shoulders and head, and she began pumping her cock in and out of my mouth.

Here I was, once again being a girly gurl, being a slut, with cocks in both of my holes, this time bent over a chair in the back room of a store. There was just a moment when I wondered how I got here, but the pleasant feeling in my ass as Kim gently fucked me, and the challenge of the much bigger cock in my mouth, pushed any wonder, any worry, out of my mind. There were cocks in me, and I was enjoying them. Very shortly there would be cum inside me somewhere, and that would feel good too. For the moment that was all I needed to know.

Behind me Kim varied her strokes, sometimes long and slow, sometimes hard and fast. Her balls slapped against my own, and the sound of flesh on flesh supplanted the voices of three people quietly moaning in the quiet room.

"Doll, you are a great cocksucker," Penny said. "If I don't get the chance to fuck you today, I'd be quite happy to cum in your mouth."

"She cums a lot," Kim added. "Be ready if that happens." They both laughed, and I redoubled my efforts to produce cum from both of them. I'd slid over an edge here, and was listening only to the feelings of pleasure my body was producing. My cock was rock hard, but it was difficult to stroke it balanced as I was on my knees, with my thighs so close together. But I could feel it -- every time Kim's strokes made my rod move, I felt myself creeping towards orgasm.

The two cocks were dancing to their own tunes in my holes, out of rhythm, and my body was jolted back and forth as Kim's hips pushed me forward and Penny's cock trying to wedge itself into my throat pushed me backwards. Kim took hold of my hips, pulling me against her as she pushed forwards. I became that cum dump, willing these two to fill me up. My own moans, wordless because of the giant ram in my mouth, almost drowned out the moans of pleasure from either end of me. I was ready. I wanted that giant cock. I'd try it.

I pushed Penny away, out of my mouth. I couldn't quite find the words to express my feelings at that moment, and I was quite out of breath. I just looked up at Penny's face and said, "Switch." I drew my hips forward, releasing Kim's cock from my ass. She trotted off to clean herself in the ladies room, while Penny moved behind me. Opening the lube again, she poured it into my ass crease, catching it with her hand. She spread lube around the opening, then once again penetrated my hole with two thick fingers. I moaned with the feel of it. "I don't know if I can handle it, Penny, but I want to try," I said, looking back over my shoulder at her.

Penny added a third finger to my ass, gently stretching me further. It hurt a little, but my moans were as much about pleasure as pain. Penny reached down and stroked my cock and balls, playing with them gently, as she pressed deeper inside me. About that time Kim came back into the room. Dropping some towels on the chair, she knelt in front of me and kissed me. "You're sure, baby?" she asked. I nodded, my face drawn taut in pleasure and pain, and she kissed me.

I felt Penny's fingers withdraw, and the huge knob that had filled my mouth completely pressed against my asshole. It was very slick, as Penny had been generous with the lube. She took hold of my hips, and as Kim continued to kiss me, Penny jolted forward, driving the helmet of her cock inside me, past the muscle rings and into my rectum. I couldn't describe the noise I made, kind of a mixed scream and moan (scroan?). I'm sure the only thing that kept the employees out front from calling 911 was Kim's mouth pressed hard against mine.

Everything stood still for a moment, as Penny graciously waited for my hole to get used to having a truck driven through it. Kim kissed me some more, and I decided to continue. I pushed my hips back towards Penny. Understanding the signal she let me take charge. I got a little more inside me, then pulled forward and gently pushed back again. After a few more tries, I had about a telephone pole worth of cock inside me. I put one of my hands under Kim's arm and pulled her to her feet. Grabbing her still-stiff rod I pulled it to my mouth and began sucking.

I turned my ass over to Penny's mercies, keeping a hand on her hip as a safety. I started bobbing back and forth between the two cocks, slowly, gently. Penny began fucking me. Kim began fucking my mouth. My ass felt incredibly full.

Was it a guy thing, that I wouldn't admit defeat? Was I a woman who wanted badly to completely please her lover? I couldn't say -- but I wanted all of that motherfucking cock inside my ass. The going was slow for a long while. Finally, after 10 minutes or so, Penny's hips touched my ass. I started pushing back harder. I had taken it all, now I wanted Penny's cock to fill me to overflowing. If she came that much, I wanted a puddle of it on the floor under my boy-pussy. At the other end I started fucking Kim's cock with my mouth. I pulled her hard against me, until she was sliding inside my throat and my nose was pressed into her belly with each stroke.

"Baby, you are so tight back here, you're strangling my cock. I'm gonna cum soon, and fill your ass full of Penny's jizm," Penny rasped.

Kim moaned gently as I fucked her cock. I had never felt so full, and in a strange way, fulfilled. The biggest cock I'd ever seen was inside me, and I was pleasing a woman I'd become quite attached to with my mouth.

Kim said, "Tell me when you're ready, Penny. I want us both to fill this girl with cum. I want it streaming out of her at both ends.

I let them take over, take me, use my body for their pleasure. I held onto the chair while I was rapidly fucked in both ends. Penny had stretched me beyond any normal measure. Kim was in my throat with each stroke.

"Soon, baby," Penny moaned.

"I'm gonna cum in her throat," Kim replied

Penny gave up any pretense of gentleness, and pounded me with her massive prick. Kim took hold of my head and fucked my mouth. I was aware of nothing other than those two penetrating poles. I wanted their cum. I squeezed my lips around Kim's cock, squeezed the muscles in my ass around Penny's mighty penetrator, and held on for dear life. The chair was even moving as they fucked back and forth into my holes.

"Now, Kim, NOW!" yelled Penny, her voice rising.

Kim took one more hard stroke, then pulled my head against her belly, her cock buried in my throat. I felt it jump and twitch as she came directly into my stomach. Behind me it felt like a fire hose had gone off in my rectum, as spurt after spurt of hot cum was forced up inside me by Penny's rapid strokes. With both pressed so hard into me, my spine was being compressed. Kim finally relented so I could breathe. She squatted in front of me and kissed me, then put my head on her shoulder and hugged me tight against her. "Baby, you're crazy," she whispered in my ear. Then she kissed me again.

Penny slowly eased out of my ass, and I could feel a breeze blow through the gape she'd left there. Her cum dribbled out of me in a steady stream. Kim helped me to my feet, then laid a towel over the chair and I sprawled out over it. Penny's cum poured out of me, soaking the towel.

Kim leaned over me and kissed me. "After all that, I can't let you leave here with a case of blue balls," she said.

With that she got on her knees in front of me and moved my legs apart. Even with all the distraction of having an artillery piece shoved up my ass, my cock was still halfway hard. She took it in her hand and took the entire thing in her mouth. It didn't take long for me to get back up to full stiffness, and she sucked like she'd never see cock again. Penny came back in and gathered up her clothes. As she bemusedly watched, she put her big girl panties back on and began the transformation back into Bob.

I smiled back at Penny turning back into Bob, then closed my eyes to concentrate on what Kim was doing to me. I had just gotten my breath back before she started, and now my heart pounded and my breath rasped in my sore throat as she sucked me to orgasm. I felt my ravaged asshole trying to squeeze shut as she had her way with my prick. Finally, I was there, there, THERE, and my load exploded into her mouth. My whole body twitched as I pumped cum into her. She kept sucking until she had every bit and my cock was completely clean.

The two of them pulled me to my feet and walked me to the bathroom. Bob went back and collected my clothes, hanging them on the back of the door as I sat on the toilet dripping out the last of his load.

"Come up front when you're dressed," Kim said, and kissed me. Then they left me to my own devices. It took a few minutes and a lot of soap and towels, but I managed to make myself respectable enough to be seen in public. I threw the towels in a laundry bin there, dressed in my boy clothes, and went back to the fitting room. Everything I'd laid out was gone, so I went back out into the store and met Bob and Kim at the front. Kim put her arm around me, bumping her hip against mine and smiling at me.

Bob smiled and handed me a gift bag. "We'll settle up another time," he said. "You've got me too worn out to work the cash register. That doesn't happen very often."

I thanked him profusely and told him not to forget to charge me. It was important to me to pay my own way. "Today was an experience I won't soon forget. In fact, I think I'll be feeling it for quite a while."

They laughed, and Kim and I left arm in arm to go looking for some dinner.

AUTHOR'S NOTE:

Sandy's had some very serious experiences. His world has been broken wide open, and he's slid into an alternate universe. We're not close to any conclusion, so I'll keep working on more chapters. If you like my stories, drop me a note. Even if you don't like them, HIT THE DONATION BUTTON. This only works with my writing and your donating.

Next: Chapter 10


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