AUTHOR's NOTE: You may think this chapter starts a bit slow, but stick with it, you'll be happy you did. And then, because you liked it so much, you'll hit the Nifty Donate button, because that's what happy gracious people do.
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 irresistible. 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. Kim 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?
I didn't have to wait long. Char held the bottle above my balls and dripped lube up onto my cock, then down between my cheeks. With one hand she stroked my slippery cock while the other spread lube around my hole. I felt one, then two fingers invading my ass, and moaned around Kim's dick as it fucked my mouth.
"Here we go, baby," Char whispered, and I felt the head of her cock on my opening. She eased it in at first, then just kept going. My hole was loose enough to absorb her whole cock in one push. She was a tiny bit thicker than me and Kim, but shorter. It felt wonderful inside me.
Char fucked my hole and stroked my cock while I concentrated on the organ in my mouth. After trying different ways to open, I learned the trick -- you open your throat by pulling back on the muscles at the back of the throat. I was still holding Kim's hips, and I pulled back inside, then pulled her hips forward. The head of her cock pushed right into my throat. I held her there for a moment, then started to gag. I needed more practice.
"I felt that, lover," Kim said, "Keep doing that. I want my whole cock inside you."
I pulled her forward and opened again. I lasted a little longer this time before my gag reflex kicked in. I tried again and again until I was completely used to it.
I was unwilling to let Kim's cock go long enough to talk to her, so I just encouraged her with my hands on her hips. I pulled her forward, her cock went into my throat, and I felt my lips against her balls and her belly. I sped up the motion of her hips, encouraging her to roughly fuck my mouth and throat.
Kim moaned out, "Oh, my god, Char, he's got me in his throat. I'm fucking him there, and it's amazing!" She took over setting the speed, holding my hands against her hips and fucking my mouth.
Char answered back, "Why didn't you tell me how tight her ass is? I could fuck this end all night long."
I heard "him" and "her", and I guess that's where I was. I was too busy to think on it too much though, as the sensations in my holes, and the friction of Char's hand on my cock were driving me right out of my mind.
I moaned loudly, my hips bucked. I squeezed Charlotte's cock with my ass. I wanted to feel the cum spurting out of me, and the cum spurting into me at both ends.
"Oh, Sandy, Sandy, you never cease to surprise me," Kim moaned, "I'm going to cum right down your throat, baby. Are you ready for it?"
All I could do was nod with my throat full of cock. I wrapped my lips tight around Kim's rod and practiced breathing through my nose on her outstrokes. At the other end I squeezed Char's cock as hard as I could with my sphincter on each in stroke. Char pulled my hips up to meet hers as she started power-fucking my hole. I'd adjusted to her girth, and she knew I could take it.
I felt both pricks stiffening as they got closer to climax. Char came first, slamming into my ass with each spurt of semen from her cock. She squeezed my rod as she came, and that was all I could stand. My cum spurted into the air and up onto my belly and my bra.
It took Kim a little longer, a few more strokes. She grabbed my shoulders and pulled my head into her crotch, driving her cock deep in my throat. I couldn't taste anything there, but I could feel her cock pumping cum right towards my stomach. I didn't even need to swallow. Her balls were against my lips, separated by my nose.
Fortunately Kim fell off to the side and pulled her cock out of my throat before I suffocated. Char fell onto my chest and kissed me as her cock slid out of my boy pussy. Both of our slimy cocks were trapped between our bodies, and we kissed and caressed as we regained our breath (Hmm, that's poetry.)
"Hey, you, that's my boyfriend," Kim protested, pushing playfully at Char's shoulder. Char laughed and said, "Then get over here and kiss her!"
Kim turned around as Char slid to the side. They took up places under my arms and took turns kissing me and each other.
"We're not done with you, sweetie," Kim whispered. "Can you stay the night?"
"I planned on it," I said, smiling up at her. "I want to make love with my girlfriend (kissing Kim) and her girlfriend (Kissing Char), then fall asleep feeling your heart beat near mine."
"Awww, she's so cute!" teased Char. "I think we'll keep him."
That brought a round of giggles.
Char pointed to the bathroom and sent me off for hot washcloths. Kim got up and padded off to the kitchen to fetch cold drinks. We reconvened on the bed and chattered like a bunch of teenage girls.
We stayed that way until Charlotte noticed my cock starting to swell......
AUTHOR'S POSTSCRIPT:
And there's Chapter 9, and we're not even through this night. There's a lot more to do here. There will be several 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.