Sandy's Journey Pt. 02

CHAPTER 8: Comes the Dawn

It was the whispers and giggles that woke me. I was spooned against Kim, both of us naked under a blanket someone had thrown over us while I slept. I opened my eyes to see Dave and Judy standing beside the bed in matching terry robes. Kim was awake and the three of them were whispering morning greetings. I smiled and added my voice, with no reason to whisper any longer.

"How you doin', Sandy?" Dave said with a smile. "Sleep Well?"

I pulled Kim against my chest and hummed softly. "Couldn't be better." I said, bending to kiss her shoulder.

"Coffee's on," Judy said. "Why don't you guys catch a quick shower and join us in the kitchen?"

With that they wandered off. Kim and I kissed and cuddled for a few more minutes. There were giggles, there were smiles, I tickled her ribs and she pulled on my cock, then we got up and went into the adjoining bathroom. It was big, with a giant shower room. We figured out how to turn on two of the large overhead nozzles and took to washing each other with the soap and sponges provided. More tickling and giggling ensued.

I was just lost in this girl, and the feeling seemed mutual. Our erect cocks rubbed against each other, then were trapped against our bellies as I pulled her to me. We were almost the same size, and everything seemed to fit. Our arms wrapped around each other, we kissed, our tongues dancing together, our eyes closed.

Then all of a sudden there were other hands, other arms wrapped around us. I looked around and found Dave and Judy had made us into a sandwich.

"I guess we need one more round before you're ready for breakfast," Dave said into my ear. "Besides, the coffee's not quite ready." They almost had to pry us apart, but soon Dave had me pressed against the wall, his hard cock rubbing against my ass cheeks. Next to me Kim had her back against the wall while she and Judy kissed. I could see that Judy had taken hold of Kim's cock,while Kim's hand groped Judy's pussy.

"There was one thing I didn't get to do last night, girl," Dave whispered into my ear, "And you're not leaving until I've sampled your pussy."

Next to me Kim said, "You, madam, were a bit too bossy with my new girlfriend last night. I think you need a little lesson in humility this morning." With that she took Judy by the shoulders and turned her around until Judy's belly was pressed against the wall next to mine and we were shoulder to shoulder.

Dave and Kim stood behind us, holding me an Judy against the wall with one hand while the other soaped our assholes. Judy groaned and pretended to fight, but her smile gave her away. We were facing each other and her eyes glowed as she looked into mine.

"Are we ready, boss?" Kim said. I guess Dave just nodded, because I felt his cock sliding between my cheeks. It was bigger than Kim's, but I was stretched enough that the entrance didn't hurt much.

Judy and I faced each other. She grabbed my hand and pulled it down to her pussy, then reached over and grabbed my cock as Kim penetrated her ass. Both of us pushed back against the rods penetrating us, reaching out to take in more, harder, faster. My fingers found Judy's clit and toyed with it. She squeezed my cock hard, then began stroking it.

Dave took hold of my hips and pulled me back against him. His big prick pressed deeper and deeper into my ass, and I loved it. I couldn't have told you whether I was boy or girl at that moment, and it really didn't matter to me. Eveything was about the physical pleasure coursing through my body, and the comfort I felt in being with these people.

Kim took hold of Judy's hips and fucked her ass hard and fast, jolting her against the wall. "Are you my little girl today?" she asked, and Judy laughed and nodded.

Dave was taking long slow strokes up my rectum, pulling out until just the head of his rod was inside me, then pushing the whole length into me. With each stroke I squeezed my sphincter to squeeze him, loving the feeling of fullness, of a hard rod all the way inside me.

I pressed two fingers inside Judy's cunt, but the angle was difficult, so I just went back to stroking her clit. Dave reached around and held Judy's hand on my cock. The two of them stroked me together, then Dave's slid down to hold my balls.

None of us were going to last long at this pace. Kim was pounding Judy's ass in mock punishment, and went off first, announcing her orgasm with a moan and slamming Judy's hips against the wall. I pressed Judy's clit hard, and her legs trembled as she came. Her juices soaked my hand as I slid a finger inside her.

Judy said, "I want to taste her cum" and slid to her knees, with Kim's cock popping out of her ass. Then Kim joined her. Dave pulled me away from the wall and turned my body towards them. Kim and Judy took over stroking my cock and balls. Dave held onto my hips and began pounding his cock deep and hard into my rectum. Kim kissed me, saying "Cum for me, baby. Cum in our mouths while Dave cums inside you."

Two tongues worked their magic on the rigid pink tip of my prick, and the rod buried deep in my ass pressed my prostate. I could no longer resist, and my load spurted out into the two waiting mouths. My asshole clenched, and Dave bellowed behind me as he shot his load way up inside me.

Judy and Kim kissed over the head of my cock, trading my cum back and forth between them. I leaned back into Dave, squeezing his cock inside me and pulling his hips against mine.

A little part of my mind, the only part not concentrating on the feelings between my legs, remembered that Kim had called me "her new girlfriend," and felt great warmth from that feeling.

We shifted ourselves apart and back to two couples. Dave and Judy turned on more shower nozzles and washed each other. Kim and I did the same. There were big soft towels and robes there for us. Judy and Dave gathered their robes from the floor and the four of us went off to the kitchen for breakfast.

The coffee was ready. I helped Judy prepare eggs, bacon and toast, and we settled in to a nice light breakfast. Kim sat next to me and held my hand when we weren't busy eating. Judy smiled at us, understanding the emotional attachment we'd made in such a short time together. Dave cracked jokes and made sure everybody had enough coffee.

I looked up at the clock and realized it was almost noon. It was time for this little idyl to break up. Normal life called, though I really didn't know what that would be like. Kim and I went around and gathered up our clothes. Judy gave me a bag for my soiled undies, and I went commando. Kim slipped back into her jeans. They were tight, and I loved watching her ass wiggle into them. Dave and Judy saw us out with kisses and hugs all around.

Kim and I walked out to our cars hand in hand. We stopped and kissed.

"See you soon?" she asked, smiling at me.

"Yes. And yes. And oh, by the way, absolutely yes." I said, and she laughed and kissed me again. "I know you have my number," I said. "Last night was pretty amazing, and I want to find some time for just you and me."

"Absolutely yes," She said. We stepped away to our cars, eyes locked, smiling at each other, letting our hands slowly come apart. I watched her walk to her car, get in and drive off waving. Then I left, heading home.

What had been just a little germ of an idea had turned into something that changed my life.

What would be next?

CHAPTER 9: Me and my gurl, and her gurl?

The world returned almost to normal. The rest of the weekend passed. I did some more online shopping for lingerie. It suited my new sexual role as a bottom for men and men who dressed like women. I'd become quite addicted to cock. I loved the look and feel of women's undergarments. But I was still mostly a guy. Don't ask me to to explain it, just go with the flow and enjoy my story.

Kim texted me Sunday night:

KIM: Hi, it's Kim. Save this number. It's private.

ME: Absolutely

KIM: You're silly. I like that.

ME: You're absolutely wonderful. I like that.

KIM: (smile emoji)

ME: I want to see you soon. Coffee, miniature golf, wild sex, whatever you like.

KIM: I hate miniature golf

ME: So do I, but you'd be worth it.

KIM: Okay, I'll be in touch. I'd like you to meet some of my friends.

ME: You'd even be worth that

KIM: (tongue stuck out emoji)

ME: Whatever you like, just make it soon

KIM: Yup. G'nite. (kiss emoji)

ME: (10 kiss emojis)

I saw Kim in the office once during the week. There was no PDA, just a quick smile and "How are you" in the hallway. Keeping the personal separate from the business, as Dave had said. Of course, Dave was my boss' boss, and I saw him fairly often. Not a clue was given, just complete professional behavior. No indication that he had fucked me in the ass in front of his wife and my newfound transgender lover.

I knew it though. When we were in the same room, I could feel my boy pussy tingle, and I found it hard to keep my eyes off his crotch.

Kim called me on Wednesday night, and we talked for a while. We teased, we flirted, we talked really dirty to each other. I told her about the new lace panties I was wearing, she told me how hot that sounded. Then she told me she was going out with a couple of her friends on Friday night and asked if I'd like to meet up with them somewhere. The idea was just to introduce me, but allow space for me to get away if the meeting seemed uncomfortable.

We talked it over for a while -- who her friends were (two other trans women), where we should meet (a trans-friendly bar), what I should wear (boy clothes on the surface, something sexy underneath), and what might happen (nothing, or everything, depending on how we all hit it off.) I agreed to meet them, and we set a rough time. They were meeting for dinner and would head for this bar later, and she'd text me when they got there.

I spent all day Thursday thinking about it. I went through my growing lingerie collection that night trying to decide what to wear. I ended up picking out a new set like the one I'd worn to Dave and Judy's, this time in black. The panties were a lacy thong, with a 2" skirtlet around the edge. The matching bra was very flat so as not to show under my male clothing. I picked out a pair of lacy black thigh-high stockings to match. After thinking about it a bit, I took the next step towards femininity, shaving everything below my neck. I was going to wear long sleeves so my hairless forearms wouldn't be obvious.

Friday I wore a white nylon thong under my office clothes. Lace on my ass felt wonderful, but I was really beginning to like the way a thong string felt creeping up between my cheeks. After work I went home and played for a little while. I put some CD porn on the computer and fucked myself with my largest dildo. If stuff happened, I wanted to be stretched. I brought myself to the pre-cum stage with my hand but didn't finish, saving myself for who knows what.....

I wasn't in a hurry -- we weren't supposed to meet until 9 or so. I took a shower and just lounged about in a robe for a while, reading news on the net and half-watching a baseball game on TV. I started getting dressed about 7:30, slipping into my bra and panties, then sliding my stockings on. It all felt so sexy.

I looked at myself in the mirror and thought about my femininization. I didn't want to let go of my male self. I was still bi, and still got horny at the idea of fucking real pussy. I especially liked licking real pussy -- the taste, the smell of female sexual excitement, smooth thighs locked against my head as I sucked on a real clit and brought on a true female orgasm.

At the same time, I had really enjoyed Dave's big male cock in my mouth and ass. The feeling of willfully giving myself to that pleasure, not in submission but as a willing partner to the sexual act. And Kim, oh God, what she did to me. That wonderful feminine body, the smells and taste of it, and her perfect cock. She just seemed to match who I seemed to have become. Plus she was sweet, and funny, and pretty, and just fucking perfect somehow. "Just be what you are today, Sandy," I thought.

I put on a long sleeve henley and jeans, and found myself humming and smiling. I was going to meet my girl, and I guess I was her girl too.

I and headed downtown about 8:30. I wanted to be nearby when Kim texted me. I found a decent parking place for a change and went into a sports bar around the corner from where we were supposed to meet. There were some handsome guys around, and I wondered what they would think if they saw what I was wearing underneath my boy clothes. Would they think I was hot? Would they want to fuck me? Would they want to compare lingerie with their own? There was one blonde guy wearing tight jeans with a big bulge in front. I tried not to stare too long.

Kim texted a little after nine, and I told her I was around the corner and would join them shortly. I finished my drink and walked over to the bar, a place called Fleetwood's. There was a DJ in the corner playing music, and looking around I quickly found Kim seated with her friends. She was seated facing the door and quickly saw me. She got up and met me near the table, greeting me by molding her body to mine and delivering a searing tongue-lashing kiss. I would have been embarrassed if it didn't make me so horny.

She introduced her friends. Charlotte was a blonde, and like Kim, highly passable. Penny was taller, and a bit gangly, with large hands and a just-noticeable adam's apple. All of them were perfectly dressed and made up. Kim was ravishing, in a classic little black dress with matching shoes. The other girls ooooh'ed and aaaah'd and teased Kim about her cute new guy, and we settled into normal bar small talk. A few people were dancing, and now and then a man or woman or trans would ask one of the girls to dance. Kim refused, but Char and Penny enjoyed the attention. There was a very tall trans girl who found Penny irresistable. She joined us for a bit, introducing herself as Jane.

The DJ found something slow to play, and Kim and I danced, her body fitting perfectly to mine.

"You've made a good impression," she whispered to me. "The girls like you."

"They're very nice," I replied. "I can tell the three of you are a tight little group."

"Yes, but I've got lots of room left for you," she said, and kissed me."

We got back to our table just in time to say good night to Penny. Jane had invited her to a party at a friend's house, and they left with their arms around each other. As they walked off, Charlotte turned to Kim and said, a little too loud, "Well, somebody's going to get Penny's big cock tonight." I laughed out loud and Char looked embarrassed.

"Don't worry," I said, there are no secrets here." With that I reached inside the collar of my shirt and brought forth a black bra strap. I winked at Charlotte, who laughed hard, leaning into Kim.

"Kim told us a little about you," she said, but now I really wanna know more."

The two of them whispered to each other for a moment, then Kim turned to me. Putting her arms around my neck, she kissed me again and said, "Would you like to go back to Char's place with us?"

I looked into her eyes and said, "I'd love to, but are you sure you want to share me?"

"Oh, baby, I know there's enough of you for two," she said. "Besides, we'll have plenty of time for just us." It was settled.

The girls had taken an Uber to dinner, so we took my car to Char's place. It wasn't that far, which was good, because Kim's hand soon had my cock about to rip through my panties.

Char's place was a rowhouse, three stories, very nice, with parking in the alley. We came in through the kitchen, where we each picked up something to drink, and Char led us to her bedroom on the second floor.

Char and Kim kicked off their shoes and flopped on the bed, while I stood at the foot.

"Now," said Char, "I need to see. I have been wondering all night what you're wearing under that junior executive casual Friday outfit. Kim promised me, and you have to back up your girlfriend."

Kim nodded up and down and smiled at me. The two of them snuggled up against the headboard.

I made a little dance out of it, throwing in all the femininity I could muster. I slowly pulled my shirt up until the bottom of my bra showed, then peeled it off over my head. Twirling it in front of me, I finally tossed it to the side. I lay down on the bottom of the bed and kicked my legs up over my head and into their laps, hinting they should remove my shoes and socks. Each took care of one foot, and Char tickled me, but they both enjoyed the black stockings they found underneath.

I got back to my feet. With my back towards them, I jerked and twerked my ass as I unbuckled my belt and unzipped my jeans. Then I slowly lowered them, allowing my ass to peek over the beltline, then dropping them to the floor. I turned around to face them as I stepped out of the jeans and kicked them away. My cock was rock hard, tenting my panties. I walked towards the bed swaying my hips side to side like a lioness stalking her prey. Getting onto the bed I crawled towards the girls, languidly moving my shoulders and hips, my head low, looking up at them from under my eyelids, my hair hanging in my face.

I kept the lioness act up until my face was almost touching Kim's. Reaching out, I took her lower lip between my teeth, then kissed her, pressing my tongue into her mouth. I stopped and looked over at Char, just offering the same treatment, and she came and bit my lip, then mashed her lips into mine.

Kim pushed me hard, rolling me onto my back, and attacked my cock. She grabbed it through the panties, stroking it up and down with the cloth. Char leaned over and continued kissing me, pushing her tongue into my mouth. She shaped her tongue like a spear and fucked my lips with it, while I played along, sucking it just like I planned to suck her cock.

Down below Kim pulled my whole package out around the side of my panties. She held my balls in one hand, stroking my cock with the other. I felt her tongue swirling around the top for a few moments, then felt the mattress shift as she got off the bed.

Char took over playing with my cock. "What a perfect prick," she said. "I think I might want to sit on this later." She took her tongue out of my mouth as I felt the bed shift again.

Here was Kim walking to my head on her knees, naked, her cock proceeding her hips. She spread her knees on either side of my head. Grabbing a pillow, she stuffed it under my shoulders, bending my neck back. She leaned forward and stuffed her cock down into my mouth. She put her hands on my chest and began squeezing my nipples. Then her hips started to move and she was fucking my mouth.

I felt Char get off the bed and concentrated on my girlfriend's cock in my mouth. I'd really come to love the way Kim tasted. There was already a hint of pre-cum in my mouth as she fucked it. The tip pushed back to the opening of my throat. I bent my neck further, trying to open up and take all of her. My upper lip was close to her balls and I was greedy for every bit of her cock. I held Kim's hips and followed her fucking motion. Reaching behind her I cupped the cheeks of her ass and pulled her towards me with every stroke she took.

I felt Char getting back on the bed and cooperated as she lifted my legs and hips. She put a pillow underneath my hips and pressed my legs up and outwards. Kip put her hands on my calves and held me bent in half as she fucked my mouth.

Char stripped my panties down below my ass onto my thighs, pulling my hard cock out behind them. She bent over and hummed as she took my balls into her mouth, then licked from there down to the tip of my cock. She stopped and I heard the click of a plastic cap. I knew what was coming and waited to feel the cool drip of lube on my asshole -- or was it my pussy now?