Category: Transgender/TV Story Codes: CD, M, F, oral, anal
AUTHOR'S NOTE:
Here we have Chapter 6 in Sandy's adventures. It may be the climax (well several of them, actually.) I have a few more ideas for our hero and his new friends, so there will be at least one more chapter. 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, not necessarily in that order.
CHAPTER 6: Dinner and Dessert
Friday came. I took a few hours off at the end of the day to dress for the dinner party. I think I was doing it more for myself than for my hosts. They knew I had a fetish for wearing panties. They didn't know how far it had gone. They didn't know how femme I'd become in my fantasies. They didn't know that I really wanted to feel a cock, suck a cock, get fucked by a cock. I rushed home, hoping to find some packages. There was only one, from the lingerie site. No toys yet. I opened it as soon as I got inside. The red bra and panty set was wonderful, and fit perfectly, as did the thigh-high stockings. As Judy had requested, I'd be there in pretty things.
I jumped in the shower to get totally clean and fresh. It was time for another first. I had an electric beard trimmer and my shaving razor, and I used them to remove all the hair from my belly and genitals. On a whim, I went a bit further, shaving off the hair between my butt cheeks. I wasn't ready to shave my whole body, but I didn't want a bush sticking out around my panties.
I guess I considered this kind of a coming-out party. It seemed my hosts were interested and discreet. I was going to show them how femme I was underneath the button-down shirt of my professional appearance. It really was for me.
Emerging from the shower, I dried myself off. Shaving had made my balls sting a tiny bit. I eased it with some skin lotion, then went into the bedroom to dress. I slipped into the red panties and bra, then pulled the thigh-highs on. They came up to just below my crotch. I checked my look in the mirror. I was hot. Yes, I had my male haircut and a few other patches of hair. I wasn't a girl, but then I didn't know if I was ready to be a girl. I just wanted to play as one. Looking in the mirror, I saw a CD that I'd be happy to play with. I finished dressing. The socks and casual slacks hid a lot. I added a polo shirt and light sweater to hide my bra. It was very sexy feeling the lingerie underneath what the mirror showed to be a young business professional.
I didn't want to be too early or too late. Judy had said 6, so a few minutes after that was my goal. I let the car's nav system plot the route and watched the time, pulling into their driveway at 6:05. I'd picked up a decent bottle of mid-price wine the night before. I didn't want to look cheap, nor did I want to look like I was trying hard to impress. Momma said never show up empty-handed.
I rang the doorbell, and Dave answered within a minute. He was dressed much like I was, casual dressy. He shook my hand and welcomed me. He had a drink in his hand, entailing a bit of juggling while I tried to pass on my gift. We both laughed and he said, "You need to give that to Judy anyway. She's in the kitchen." He pointed the way, and said, "Can I get you a drink?"
"Whatever you have there is fine," I answered. I went tentatively off in the direction he'd pointed and found the kitchen at just the right moment. There was Judy, bent at the waist in front of me, getting something out of a low cabinet. Her ass was barely covered by a tight red dress. I savored the sight for only a second, then said "Hello."
Judy jumped, then laughed. "Hello, Sandy, come in. We almost got ahead of schedule there." I didn't know what that meant, but apparently there was some plan for later, something to look forward to. I delivered the wine, and then Dave came in with our drinks. We sat at the counter while Judy bustled around finishing dinner. With just the three of us, she said we'd skip the formal dining room and just use the breakfast area off the kitchen.
Judy's dress was astonishing - bright red and hugging every curve of her body. The fabric was just thick enough, and her body taut enough, that no lingerie lines showed. I found myself slightly distracted, wondering what was underneath it. At one point Dave slapped me on the back just to get my attention. His hand lingered there, and I wondered if he'd found my bra strap.
I won't bore you with dinner. It was very pleasant. The conversation was smart and amusing. Enough wine was consumed to ease all tensions. The food was excellent.
All three of us were on clean-up duty when Dave's phone rang. He looked at it for a moment, then apologized and said he had to take it. He wandered off towards the living room while Judy and I finished up.
She made coffee, and we settled into the living room to talk. Dave was nowhere in sight. "He gets business calls at all hours," Judy explained. "I hope he'll be able to rejoin us soon." Then she smiled and said, "I'd hate to start without him." She followed with a devilish grin. She lowered her head to take a sip of her coffee, and her eyes locked on mine. As I watched, her gaze lowered, and I could see it was directly on my crotch.
A moment later Dave came back in. "I'm sorry, honey, this is going to take a few more minutes. I have a little paperwork to do. Kim is coming over to pick up the final version."
"How nice," Judy replied. "Do you think she might stay for dessert?" A smile passed between them and Dave replied, "I hope so."
Dave went back towards what must be a home office. Judy put her coffee down. She stood up and walked towards me. I started to get up, and she signaled me to stay seated.
She stopped just a foot or so in front of me. Looking down at me, she said, "Well, Sandy, you're all mine for a little while. I've always thought you were a very nice and very talented young man, but when Dave told me about your lovely panties, it added a whole new dimension."
She put her hands on her hips and began to swivel them. She moved her feet apart. "This new part of you interested me very much."
My eyes didn't know where to look. Hers bored into my face, but those hips wriggling hypnotically drew my eyes.
She stepped forward, one leg between mine. Her hands moved around her hips, up to under her breasts, then to her thighs. "I think, for starters," she said, "We'll play I'll show you mine and you show me yours."
Her hips continued to move as her hands took hold of the hem of her dress and started to pull it up. It really didn't have that far to go anyway, but very quickly the bottom of her panties came into view. Now my eyes were locked there. Her hips continued their rhythmic motion as the dress rose all the way to her waist. Her panties were just a wisp of lace, almost completely sheer. As close as she stood to me, I could see her shaved pussy underneath it.
"Feel that fabric and tell me what you think," she said. Her hips came to a stop, and she spread her feet wider than her shoulders. I reached out tentatively. They were the sexiest panties I'd ever seen. I touched them with one finger just at their top, then traced my way down. She moaned softly, and I cupped her pussy in my hand.
"That's magnificent," I said. I tore my eyes away to look up into hers, and she smiled at me.
"I'm glad you like them," she said. With a little singing voice, she added, "Your turn." She took a step back. The dress was tight enough to stay in place. She took my hands and raised me to standing. Then she turned her back to me. Her panties were a thong. Her luscious, perfectly tight little ass greeted me. She took two steps, then turned to face me again.
"Now, what do you have to show me?" she said. She cocked her hips to one side. One hand idly stroked her pussy through the lace.
I decided to go with the bottoms as she had. I loosened my belt and undid my trousers. I slowly started pulling my zipper down. I wriggled my hips seductively as she had, which brought a laugh from those beautiful lips. My pants fell down around my ankles.
My panties were a more full-cut, in red, with red lace panels on the sides. By now they were a tent, as my cock had gone to full attention while stroking Judy's pussy. "You can check out the fabric if you like," I said, pressing my hips slightly towards her.
Judy stepped towards me. Avoiding my hard cock, she stroked the lace panels, then grabbed both cheeks of my ass. "Oh, that's wonderful," she growled, her face close to mine. "Is there more?" I nodded. Taking the hem of my sweater and shirt together, she pulled them up over my head and dropped them to the floor. "Oh, you are so pretty," she said. "Just stand there."
She walked around me, her hands stroking different parts of my body as she moved. She was there at my hip, then sliding her hand across my stomach. She was behind me, her hands around the tops of my stockings. She stepped back for a moment and the red dress flew over my shoulder and landed at my feet. I felt her bra against my back, the same sheer light fabric as her panties. Her hands slid down from my shoulders to my belly. She kissed the back of my head, then each shoulder. Her hands slid towards my cock.
At that moment I heard the front door open. Very quickly a young blonde woman walked past me. "Very pretty! I'll be back!" she said with a wave, and walked quickly towards Dave's office.
"That was Kim. She'll be back," Judy said. Her progress towards my prick halted by the interruption, Judy came back around me. We stood toe-to-toe. Her breasts were as perfect as the rest of her. She brought her hands up to gently pinch my nipples through my bra, and I returned the favor. Her eyes closed for a moment as her breath caught in her throat.
"So far you are perfect," she said, "but now it's time for the skills test." Taking me by the hands, she backed towards the sofa. I fumbled out of my shoes, socks and trousers on the way, and she giggled. "Please, Sandy," she said with a smile, "make me cum." She traced my lips with a finger, then pushed it into my mouth. Hooking her finger behind my teeth, she sat down and pulled my mouth towards her hips until I was forced to kneel. She spread her legs and leaned back.
I reached for her tits again, caressing and molding them with my hands. I caught her nipples between my fingertips and softly squeezed them. She moaned softly, then took my head in her hands and pressed down towards her cunt. "Girls use their mouth, Sandy," she said softly, "Now make me cum."
I kissed just above her panty line, then slid my fingers inside them and pressed the gossamer fabric aside. Cupping her taut ass cheeks in my hands I pulled her pussy to my mouth like a starving man. My tongue slid instantly between her lips. She was very wet and hot inside. She tasted wonderful. I tongued her lips, pressed hard in between them, then went in search of her clit. There it stood, bare and proud. I took in very gently into my mouth. I pressed it up against my teeth with my tongue, rolling it back and forth. Then I went back down, seeing how deep inside her I could get my tongue. My nose was near her clit, and I rubbed it as I licked the juices from inside her cunt into my mouth.
Judy was in charge. She had told me what she wanted and I'd quietly obeyed. I stuck my tongue out and licked from her perineum up all the way to her clit. Taking it in my mouth again I closed my lips around it and sucked hard. Judy's hips spasmed in pleasure. I changed it up, spreading her lips with my fingertips to completely expose her clit, and flicked it back and forth with my tongue, then sucked it into my mouth again. While I concentrated there, I pressed one of my middle fingers deep inside her, curling it to stroke the upper wall of her cunt.
Judy moaned. Looking up, I could see she was pinching her nipples. I felt a slight tremble in her thighs, and she spread them wider, then pressed my head deep into her pussy. I added a second finger to the first inside her, flicking her clit harder with my tongue. I held my fingers stiff and fucked her juicy cunt. Her breathing quickened. Her hips undulated, rising to meet my penetrating fingers. Her cunt started squeezing rhythmically. I wrapped my lips around her clit again and sucked it into my mouth, rubbing my teeth across it, then licking the tip.
Her moans got louder, and she called out my name. "Sandy, ohhhhh, Sandy, you wonderful cunt-licking girl! You're making me crazy! Suck on my clit some more!"
I fucked her harder with my fingers, then withdrew my middle finger. Covered with her juices, it slid right between her nether cheeks to her asshole, and penetrated easily to the first knuckle. I just had to change the angle of my hand a little, then started finger-fucking both her holes while I licked and sucked her clit. I still had one free hand, and I slid that up her belly to her tits, squeezing each nipple in turn.
I was breathing as hard as she was. My cock was rock-stiff, still rubbing the walls of its satin prison. Judy began to tremble. It started in her hips. Her holes clenched at my fingers, and I fucked her harder. Her legs trembled, her breath caught in her throat, then she roared out, "OHHHMMMYYYGOODDDD!" and soaked my hand and face with her squirted juices as she came.
I didn't stop. I kept going with all my energy. I wanted to make her cum until she couldn't take anymore. Her thighs slammed onto the sides of my head, and she kept moaning and screaming my name. "Fuck, fuck FUCK, SANDY! So good, so GOOD!"
Finally she went completely limp, and pushed my head away from her dripping cunt.
She lay back on the couch, breathing heavily. Looking up behind me, she said, "Oh, Dave, she's goooooooodddd."
I'd been a little busy and hadn't noticed we'd drawn an audience. Looking around, I found Dave and Kim standing there smiling at me. Dave was naked, and Kim lazily stroked his cock. Kim was fully dressed, a folder under her arm.
"Kim, you're not staying for dessert?" Judy asked.
"I'd love to, but I have to deliver these in person," Kim replied, "I hope to see more of Sandy some time soon. Love her outfit, and I can see she has talent."
Kim leaned in and kissed Dave on the lips, then stepped over to kiss Judy. She ran a fingertip through Judy's dripping pussy lips and stuck it in her mouth. "Mmmm," she smiled. Bending over me she tilted my head up and pressed her lips to mine. Her tongue pushed through my lips and danced with my own for a few seconds. "Next time we'll compare panties," she said, and headed for the door.
"Sorry you have to run," Dave said as she left. Turning to the two of us he said, "Shall we have some refreshment before I have my dessert? We nodded and he led the way back to the kitchen. He brought out some brandy and poured three small snifters. "Something to give us a little strength."
Judy excused herself to clean up a little, taking her drink with her. Dave took a sip of his, then said, "What do you think, Sandy?"
I sat still for a moment. "I don't know, Dave. I'm in a world that's entirely new to me. A few weeks ago I was just another straight schlub. Now I'm sitting here in lingerie, sipping good brandy, having just finished ravaging a beautiful woman I've always admired, and wondering how her husband's cock will taste. And by the way, he's one of my superiors at work."
"Don't worry about that last thing, Sandy. Judy and I may bring people from our work lives into our private life, but we never let the two mix. Whatever happens behind closed doors is completely separate from our work together. Whatever happens here is completely up to you. You can say no more at any point, and we'll still get along just fine."
"I'm glad to hear that, and I am really very interested in sucking your cock," I said.
"Let's see what we can do about that," said Judy, coming back into the kitchen. She walked around the counter, put her arm around her husband, and kissed him. She was completely nude, and the they made an extremely handsome couple.
The two of them smiled at me. I raised my glass to them, saying "Then let the games continue!" They touched their glasses to mine and we all drank. Taking my hand, Judy led me across the living room and down a long hallway. There was a soft light coming from a room at the end. Stepping into the room, I could see it was dimly lit by small lamps placed on random tables. In the center of the room was the largest bed I've ever seen. On and around it were pillows of large and small sizes. Dave and Judy dove into the center of it as I stood taking it all in.
Judy whispered to Dave, and they moved into a 69 with her on top. She sat down, pressing her pussy against his mouth. Leaning forward, she took his cock in her mouth. She kept her head tilted up, looking me in the eye as she sucked her husband. I got onto the bed, walking to them on hands and knees. I could hear slurping sounds as Dave's tongue dug into Judy's cunt. I remembered how wet it had been, and how wonderful it tasted. I got up between Dave's knees. Judy put her hands on Dave's thighs and spread them wide. Then she held his balls with one hand. The other stroked his shaft as her tongue circled the helmet on top.
It was an average cock, about 6" long, no thicker than my own, and in general not much bigger than the dildo I'd been playing with. It wasn't some giant porn cock, it had no magical powers, and yet it was the thing I wanted most in my life at that moment.
Judy sat up a little. She stroked Dave's prick with one hand. She smiled at me and pushed it so that it was pointed at me. Perhaps I looked a little nervous, because she nodded her head in encouragement. I moved closer. She took my hand and placed it around his cock, putting her own hand over mine and starting a stroking motion. She removed her hand and made an O with her lips, and just watched me.
Reaching down, I cupped Dave's balls in my hand. His sack was a bit bigger than my own, and I had a fleeting thought that it was full of cum that I would soon taste. I leaned forward and opened my mouth, and slowly pushed down, taking the rod in my mouth.
The taste was even better than I dreamed, and there was a little something more, obviously precum. I liked it. I sucked hard, pulling on his prick with my mouth, then descended further. The head poked at the back of my mouth, at the edge of my throat. Pulling off, I licked it from bottom to top, wrapping my tongue around the edges, then holding the head in my mouth while my tongue licked the frenum just below.
I wanted to check out his balls. I held his cock against his belly, stroking it with my hand. I licked his shaved balls and tried to get them in my mouth. The whole sack wouldn't fit, so I gently mouthed each ball separately, then pushed them up and licked across his perineum. I must have been doing good, because I could hear Dave moaning softly into Judy's cunt.
Judy got up off of Dave. Moving around, she grabbed a large pillow. Getting Dave to sit up, she put it behind his back so he could watch me suck his prick. Then she kissed him and moved down beside me. "Good girl," she whispered to me, kissing me on the cheek. Then she moved down behind me.
I stuck Dave's cock back in my mouth. I used my hand and mouth together, fucking his cock like they were a pussy. My other hand massaged his balls, pulling gently, holding, squeezing, then teasing his perineum with the tips of my fingers.
I felt Judy's hands on my hips, softly caressing. She stroked my back, my shoulders, and my waist, then came back to my ass. She used her palms and her fingertips, tracing and caressing my muscles as her husband's favorite muscle was massaged by my mouth.
Her fingertips found the waistband of my panties, and she began slowly sliding them off me. She had to reach inside the front to keep the tip of my hard cock from catching. Her fingertips on my cock felt like an icy fire, cool to the touch but promising fireworks. It was the first time either of them had touched my genitals.
I varied the use of my mouth and hands on Dave. I looked up at him. He had his hands behind his head and he smiled as I inhaled his prick.
Judy got my panties down over my ass, and I lifted my knees so she could remove them completely. She tossed them aside and started caressing my ass cheeks. She dragged her hand between my thighs and I spread my legs farther apart. The back of her hand ran across my balls, and I moaned at the contact. She spread my cheeks, and I felt her hot breath on my boyhole. Then I heard a plastic cap.
I knew what was coming and I smiled. I renewed my assault on the spear in my mouth, pushing deep to get more inside me. I couldn't quite open my throat, and I knew that was a skill I'd have to figure out if I was going to continue sucking cocks. I felt the cool liquid drizzle between my cheeks and run down to my asshole. I felt Judy's fingertips stop the flow, and then I felt the most amazing thing yet -- her fingers rubbing lube into my asshole.
She rubbed around the edges, lubing the whole ring. Then a fingertip pushed tentatively at the opening. In a moment it popped through and began sliding up inside me.
"She's a tight little girl, Dave, absolutely virgin. I think you'll be very happy." She said.
Dave moaned softly. I moaned louder as her finger started fucking in and out of my hole. Then her other hand reached between my legs and grabbed my cock. I opened my legs even wider, and fought to keep my attention on what I was doing with my mouth. It's hard to suck cock and moan at the same time.
Judy added a second finger to the first, squeezing it into the tight opening and finger-fucking me just as I'd done to her pussy.
I didn't know how long I could hold out, but I was determined to make Dave cum before I did. Judy's fingers ranged deep inside me. Her hand on my rod was maddeningly sexy.
Then she stopped. Her hands left me and she backed away for a minute. I soon knew why. I felt the tip of a prick sliding between my cheeks. I guessed a toy from some stash near the bed. It felt so good, sliding up and down, fucking my cheeks. Then two hands held my cheeks apart, and the cock was pressed against my hole. As it started to slide into me, two more hands held my hips. Wait.....what?
I pulled off of Dave's cock and turned my head. Kim! She was nude, her hands on my waist, while Judy held my cheeks apart. But the cock?
A quick look confirmed it was Kim's. She was like me, but obviously much, much more advanced.
"I told you I'd be back," she said, and giggled at me. "Now finish showing Dave what you can do with your mouth while I make your ass very happy."
With that she slowly sank her cock into me. It was perfect for me, just the right length and thickness. Soon I felt her balls against mine, and I went to town on Dave's cock. I fucked it with my mouth and hand. I played with his balls, I caressed his belly, even reached up to pinch his nipples.
Kim's cock was like, the last and best miracle of the night. It felt amazing sliding in and out of me. Judy's hands were everywhere -- exploring the junction where Kim's cock entered me, then stroking my balls with just her fingernails. She came up beside me for a moment, and taking my head in her hands, pushed it up and down on her husband's prick.
"Your ass feels wonderful, Sandy," Kim said, "I think we're going to be friends."
She spread my cheeks wide with her hands, trying to get every last tiny bit of her wonderful cock into me. Then she reached around and began masturbating me in time with her strokes. Every time she pushed in, her hand ran down my cock, like I was being pushed from both sides. It was magnificent.
Judy moved back up to Dave. Sliding the pillow back, she crouched over him and once again pushed her cunt down on his mouth. Then she laid her head on his belly and watched me suck his cock from inches away.
She was still in charge. "Kimmie, fuck her good. Show her what that hole is for." She said.
Then, "Oh, Dave, your tongue is wonderful. Would you lick my ass?" And, "Sandy, your mouth should be a registered landmark. What you did to my pussy, and what you're doing to Dave's cock. You know he's going to fill your mouth with cum, right. And you'll love it. And you'll share it with me and Kim.
Kim continued to pound my ass. You could hear the sound when her hips slapped against my ass. It felt amazing -- just enough friction, just enough lube. I tightened my sphincter as she drove into me, generating an "Ohhhhhhhh" from her mouth each time I squeezed her cock. Dave began to moan, and I felt his thighs tense. It really wouldn't be long before another fantasy was fulfilled.
I could see Judy's face tighten as Dave ate her ass and pussy to a frenzy. Simultaneous orgasms are a myth, right?
Not tonight.
Dave grabbed my head and forced it down on his prick, and I felt his hot cum hit the back of my throat. Pulse after pulse, filling my mouth. God, how much would there be?
Judy screamed, and at that moment Kim drove hard into me, and lay over my back. I could feel the spasms of her cock as it spit a load inside my ass. I could feel her small breasts on my back as they heaved, trying to catch her breath.
Dave's cock finally quit, and I had a mouthful. Judy had rolled off, laying on her back with her head on Dave's belly. Pulling off my first cock, I pressed my lips against hers. She opened her eyes in surprise, then opened her lips as I shared part of her husband's load.
Kim pulled her softening cock out of my ass, Even that felt amazing, with her cum dripping from my hole. She put her face near mine, brushing her blonde hair out of her eyes. She opened her mouth and I dribbled the rest of Dave's cum into it.
What was left in my mouth I swallowed. Not bad, I thought. I've tasted better things, but getting it was so much fun, and that makes it taste better.
I didn't want to add to the load of bodies, so I rolled off to Dave's other side, lying there on my back by myself. The only sound in the room was heavy breathing, as we each calmed our heart rates and got our breath back.
In a very few moments I fell asleep.