Tinas Play Thing

This story is Part 2 of the series.

This is a work of fiction.

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Tina invited me to a get-together at the home of one of her long-time friends. She said she had known most of the guests since middle school and they got together about once a year. "I owe most of my success to this network of friends. Tonight, I want to begin to pay them back for all that they have done for me." I wasn't sure how I could help her, but I was willing to play along.

I was finishing up when Tina stepped into the large walk-in shower. God she looked good naked. She came over to my place straight from work and was getting ready with me.

"Turn around Sissy and spread them for my inspection."

I loved it when she switched on her Dominant persona. She reached around and gripped my cock with her soapy hand while she applied pressure on my asshole with a finger from her other hand. She was sliding a soapy finger in my butt while whispering in my ear. "I have to make sure my Sissy is ready for tonight. You have to keep your pussy clean and prepared for anything, baby."

The finger slid inside and she began thrusting in and out. I bent over even more and put on a show for her. I even grabbed my buns and pulled them apart while I whimpered for her. "Such a good little Sissy. Tonight is very important to me. You're going to do everything I tell you to do. No questions, no hesitation. Just fucking do it. Got it?"

Her tone was more serious than usual and I wanted to take a moment to let her know I was willing to do anything to help her tonight. "Tina, I want you to know..."

She interrupted me, "Baby, go put on the pretty things I set out for you on the bed. I know you're going to love them, but don't get carried away in front of the mirror. I don't want to be late."

I dried off and hurried to the bedroom. I loved her special sissy gifts. She always purchased the perfect sizes, designs and colors for my body. I stood at the foot of the bed and my heart began to race. I saw a beautiful matching set of pink panties, garter belt, stockings and a lovely bralette. I had always craved a pretty thing to wear up top, but I didn't know where to begin in buying one. My chest is 44" with A cups. I'm a big V-shape. Lingerie never worked for me and bras were a mystery. I was afraid this little bralette would be another disappointment for me.

I pulled the lacy panties up my thighs and tucked my cock away. I slid the silky thigh highs up and was trying to secure the clips to the nylons. "Jesus Curt, you're the biggest PantyBoy I've ever met. How can it take you so long to do that?" She spanked my ass hard and spun me around while she hooked the back clips.

"Put on the little bra. I know it's like a dream come true for you, but we don't have time to celebrate your Sissy breakthrough. Just finish up and put on pants and a dark shirt. I don't want everyone else to know about your fetish...yet."

I held the flimsy little pink thing in my hands. There were cute little round strings that went over my shoulders and a lacy stretchy top that fit around my chest. I decided to step into it and pull it up instead of stretching it over my wide shoulders. I've popped seams in the past when I stupidly pulled a girly thing over my head. I was in heaven as the lace rubbed against my stockings and panties as it slid up. I snaked my arms through the loops and started to straighten it over my pecs and nipples. Oh my god! It was hugging me. I felt like Tina was gripping me and making me feel secure. That one little garment was amazing.

By now, my cock had completely untucked itself and was tenting in my pants as I buttoned my shirt. "Curt, I wish I got as turned on as you do just from wearing pretty things. I think it's sweet, but seriously, do something about that hard-on because we are leaving", she said as she pushed by me.

I chuckled, slid my erection under my waistband and followed her out. While I drove my pickup to the party across town, Tina filled me in on a few things. "Curt, each year someone is assigned to provide the entertainment. As we've grown older, it's become more and more competitive. We've done extravagant game nights, Monte Carlo gambling, pool parties, even a hot air balloon ride. Tonight, I'm pushing the envelope in the sexy category", she described.

"So, what do you have planned for tonight?" I asked.

"You Curt. You're the entertainment" she said as she opened the car door and we walked into the large house.

"What exactly do you mean by, 'I'm the entertainment'?" I asked.

"Oh honey, I know you're not dumb. You're wearing a complete sissy ensemble under your boy clothes. It's pretty obvious. Now when things get going, I want to impress them with your obedience and your desire to do anything kinky that I ask. Don't embarrass me, PantyBoy", she said as she stared into my eyes.

My heart began to race. "Holy shit, I'm going to get fucked again in front of an audience. They're going to see my girl clothes. Oh my god, what if there are men here? What will she make me do? What will I do? Is there anything I'll refuse to do? Fuck, I'm getting hard again!"

"Come on Sissy. I want everyone to meet you!"

We walked out onto the back deck where about 10 well-dress women and a couple of men were mingling with drinks and hors d'oeuvres. Tina introduced me as her boyfriend the firefighter to everyone as we mingled.

About half-way through the crowd, Tina leaned in close and whispered, "Baby, I've been bragging about you to my friends. Some of them know about our night at the Principal's house. I've told them all about you and they can't wait to see your little show" she said and giggled a little.

Just then, she began tapping loudly on her wine glass. "Friends, gather around. I want to tell you about tonight's entertainment! It feels like I've already told most of you about my sexy boyfriend Curt. I hope everyone has had a chance to meet him. Anyway, I know this is a little bit 'different' for this crowd, but as a gift to all of you I'm sharing him with you tonight" she said excitedly.

"You see, recently I've been describing our escapades to some of you and I think you NEED to experience what Curt and I have shared. Let's get started. It will all make sense after we begin. Curt, come and join me."

It was a lovely evening with the sun setting in the distance. Strings of tiny lights contrasted nicely against the orange glow in the sky.

I confidently stood next to Tina as she kissed my cheek. "Ladies, and gentlemen, Curt is my boyfriend. He is also my toy. All of you get to play with him tonight. Curt will do anything I ask him to do. And tonight, I'm extending that privilege to all of you. Curt, take off your shirt and pants."

With my heart racing and my hands shaking, I unbuttoned my shirt. I was very aware that each button exposed more of my cute new bralette. Everyone had big smiles as I untucked the hem of my black shirt and pulled it off my shoulders. I felt good standing with the perfect pink garment clinging to my chest.

"Oh my god. He's so cute", "Look at his nipples in that little bra", "It's so precious on him", were some of the comments I heard as I moved on to my pants. I unfastened my belt and unbuttoned the waist. Tina approached from behind me and held my chest from below my armpits. It felt wonderful to have her hands on my nipples as I lowered my zipper.

I stared into the crowd and lowered my pants. Each inch revealed more pink sexiness. The smooth garter belt was layered over my lacy panties. My cock was throbbing in them and poking straight out from my body. I began to bend over and lower my pants below the tops of my stockings. Then they fell to my feet. Tina bent down and helped me out of my shoes and removed my pants from my feet. For the second time in my life, I was standing in public in a lovely sissy outfit and loving it.

Everyone clapped politely as Tina turned me around to show off my ass. She caressed it gently then reached between my legs to fondle my balls. No one spoke. Then she pulled her hand back and spanked me, hard. I yelped and turned to face the group. "Good boy" she said.

"Before we sit down to eat, I want Charlotte to join us up here. Charlotte, come sit in this chair", she gestured to a sturdy Adirondack chair. "Now Charlotte told me she hasn't had her pussy eaten for over three years. I think that's way too long, don't you? Curt, you know what to do. Make my friend Charlotte cum in your mouth."

Now this is something I was ready for. I walked over towards the cute blonde who was trying to stand up in terror. "No, no way Tina. Not here, not now, not like this!!"

Everyone there must have known that Tina wasn't going to change her mind. This was the beginning of her "show" and she wasn't taking no for an answer. As Tina applied pressure to Charlotte's shoulders, I quickly reached up under her skirt and grabbed her string panties on her hips and pulled them right off her feet. Charlotte shrieked and recoiled. I grabbed her under her knees and pulled her legs until her pussy was at the edge of the chair. Tina leaned in and began whispering in her ear as I flipped her skirt up to her waist. She shrieked again and grabbed her naked pussy.

I wasn't taking "no" for an answer either and began licking her fingers that were hiding her little slit. She squeezed her knees together initially, but slowly began to relax as Tina calmed her and I licked. I grasped her wrists in each hand slowly pulled them away as she spread her knees for me. With her arms relaxed I moved my hands to her inner thighs and pushed them apart, wide. I spread them and lifted her ankles over the wide arms of the chair. She was spread wide open for me. I settled in for a long, slow licking.

I only tongued her very outer lips and licked a little around her taint. Finally, she let out a low moan indicating she was ready for a more focused approach. I slid the tip of a finger into her pussy and spread the slippery juice all around her opening. She moaned again and thrust her hips toward my mouth as my finger penetrated deeper. I fingered and licked and sucked as I rotated through all of my favorite techniques.

I normally get a little soft when I eat pussy, but not this time. I was on my knees, wearing an entire pink, sissy outfit as a crowd watched me eat Charlotte's pussy. I only knew her name because my girlfriend had said it five minutes earlier. And she was finally getting into it. Tina was pinching Charlotte's nipples through her little cocktail dress while I was slurping and fingering her. I curled my finger up into her G-spot and moved it around until I heard the "Oh fuck" I was listening for. Charlotte's eyes popped open and she stared at me like I had unlocked her body.

I knew she was ready for more, so I flat-tongued my way to her clit and applied pressure. With my finger on her spot inside, I sucked her clit between my lips and waited. Seconds later, she yelled "Don't stop, don't stop, don't stop!" I slipped the tip of my pinky into her ass and didn't stop eating her until she begged me to stop.

I was so happy. Tina was beaming with pride that I had helped deliver a massive orgasm to her friend. "I knew you would enjoy Curt's mouth Charlotte! Now, let's have a seat for dinner. Ladies and gentlemen, Curt will be under the table crawling around offering pleasure to anyone who wants some of what Charlotte just experienced."

Tina walked up to me and wrapped her arms around me. We hugged and then she gave me a long, deep kiss. "Mmmmm...you taste like pussy...delicious. You did a very good job PantyBoy. Take a few bites of food because I think these horny sluts are going to keep you busy during dinner."

"Thank you, Tina. I'm glad you're happy. I loved doing that for you and Charlotte. But...um...I have a question."

I was trying to find a way to ask without upsetting her or ruining this nice moment.

"So I'm very excited about crawling around eating pussy during dinner, but...there are two men here. What am I supposed to do if...? I mean, I've never done that and... I'm not saying no, but..."

I was struggling and Tina was not amused.

"What the fuck, Curt!", I thought I was perfectly clear earlier.

"I know Babe, but I need to say something", I said hesitantly.

"Go ahead Sissy. I can't wait to hear this."she spit back at me.

"Babe, here's the truth. I'm going to suck cock for you. I want to get down on my knees and give a blowjob. I do. But I want it to be special the first time. I want you to be there with me. I want you to watch and be proud and pat my head and tell me how sexy I look. I want you to call me a "cocksucker" and a "Sissy" and say it's ok. Is that alright? Can it be like that, please?" I pleaded with her.

I could see that her initial reaction was rage. She wanted to turn me around, bend me over and spank my ass until it was burning red. But then the anger left her eyes and tender smile came across her face. She hugged me for a short moment then looked in my eyes.

"Ok Curt. We can do it that way. I would also like to experience that with you. But I swear, if you pull anymore shit like this tonight you will pay. Now, you're going to make those cocks cum under the table if that's what they want. But I won't make you use your mouth...tonight."

I was so relieved. I wasn't ready to do that under a table to anonymous men. Now, I had set the ground-work for a truly exciting future experience with Tina and a guy.

As I stood there smiling, celebrating my small victory, Tina looked at me and giggled, "You're such a Sissy. Now, take off your panties and get ready for dinner. Did you bring some lube in your little purse? Of course you did. Put some on your hand and get your cock all hard and shiny. Oh, put on a cock ring! I love how you get all thick and red. Before you go to work under the table, I want you to walk around and masturbate for my friends. Pay special attention to Brenda. She told me her fantasy was for a man rub his cock for her while she watched. Brenda is in the blue dress. But don't cum yet. Save that for later, PantyBoy."

I was ready for anything at that point. I slid a black, rubber cock ring over my shaft and balls so it sat close to my body. I always shave closely down there so that it doesn't grab my hairs. I had a thicker patch of hair above my cock. I pulled out a small vial of lube from my "fuck bag" or my purse as Tina calls it. I squirted some in my hand and tucked the vial into my stockings.

With the ring tight around my package, I began slowly stroking myself as I approached the table. One woman gasped and pointed as I approached Brenda in the blue dress. My cock was so hard and throbbing as the blood was captured in the shaft. My balls were lifted forward and looked so full and round. Brenda turned a lovely shade of "embarrassment red" as we made eye contact. I walked up very close to her, my engorged tip inches from her mouth. I made an "O" with my thumb and forefinger and gently fucked my hand. I had to be careful because sometimes my orgasm sneaks up on me and I blow quickly when I'm that turned on.

I put on a good show by cupping my balls in my other hand. I switched to a reverse grip on the shaft while I pulled my balls down and covered them in lube. She was literally drooling as a dollop of yummy, clear precum gathered at the tip. I scooped it up with my finger and brought it to my lips. I sexily licked it off and sucked my finger. She let out a big sigh.

Tina approached us and said, "Jesus Curt, I thought you didn't want to suck cock tonight. You could have fooled me!" Now it was my turn to blush. I asked Tina if it was ok for me to crawl under the table and begin servicing her guests. She agreed, kissed my forehead and said, "make me proud, Sissy."

I pulled a chair out and crawled underneath. It was a very unique view of the guests. All I saw were legs with short skirts and dresses and two pairs of mens legs wearing pants. The women were all wearing cute shoes and some sexy boots. I decided I would begin at one end and move down the line. I made note of where the men were seated and gave myself some time to work up to that task.

I heard Tina's voice muffled through the tablecloth and guests legs. "Ladies, remember: my Curt is under the table ready to service you. If you want him to eat you, go ahead and pull up your dresses and remove your panties for him."

I felt like a very lucky man. Slowly, more than half of the women began to pull up their hemlines and shimmy out of their pretty panties. What a view I had of these horny women preparing their pussies to be licked.

I heard a man clear his throat and Tina said, "Don't worry Steve, Curt won't leave you out. I told him to take care of you too. Make it easy for him to get inside your pants. You and Joe will get your orgasms. I'll let Curt decide how to do it. Remember, you can play with his parts too if you're interested".

I was pleased that she set some ground-rules, but a little afraid of how she ended it. "Play with my parts too?" that left a lot to the imagination.

I decided to focus on the task at hand. I crawled over to the head of the table opposite Tina. I didn't know this woman's name, but her skirt was hiked up high and her pretty, shaved pussy was ready for me. I stuck two fingers in my mouth and got them wet up to my knuckles. I proceeded to tickle them around her hole as I exhaled into her thighs. She slumped down into her chair and spread her knees for me.

The position was a little awkward for my neck, but I stuck my tongue out as far as I could and began licking. She tasted a little salty and had a strong musky scent. I was in heaven. I figured that with all this pussy and only one mouth, I need to keep a pretty solid pace and get them off as efficiently as possible.

I overheard a woman say "Tina this is so fucking hot! Next time you have a Sissy crawing around you've got to have a glass tabletop. I'd love to watch him with his face buried between our legs. Can you imagine how hot it would be to watch him suck a guy?"

My mind wandered briefly considering how sexy that would be with an audience and Tina supporting me.

I fell into a rhythm of fingering them and licking and then adding another finger and finally clamping down on their clits until they either came or tapped out. I knew I wouldn't make them all cum, but I was committed to trying. After the fourth guest, my chin, neck and bralette were soaked in spit and girl-juice. My cock was still hard and I occasionally dropped a hand down and stroked myself. I was so hot and excited.

Then I moved over and came across my first pair of pants and shoes. "Oh shit, here we go", I thought. I decided my best approach was to jack him off like I do myself. I put my hands on his knees and slowly slid them up his inner thighs until I was caressing his balls. I wanted full access so I grabbed his belt, pants and undies and pulled them down to his knees in one shot. I suddenly felt like I was in a confined space with only a cock and balls in my face.

I pulled out the lube and dribble it into my hand. I reached up and grasped his shaft. He was ready and thankfully, so was I. I began stroking him from base to tip over and over. I cupped his balls in my other hand and played with them like Tina does to me. "Your boy is pretty good, Tina!", he shouted.

"Oh noooo", I wanted this to be private. Luckily, Tina stayed seated and simply asked what I was doing. "Oh, he's got my pants down to my knees. He's stroking me and playing with my balls just how I like it. Are you sure I can't cum in his mouth?'

"Not tonight Steve", she answered. "Unless you can convince him to let you."

"What do you say Sissy Curt? Want me to fuck your mouth? I'll give you nice mouthful of what's in those balls you're playing with."

"No thanks", I mumbled from under the table. "I'll just jack you off tonight". I sounded pretty weak and didn't like the feeling. Sure, I was on my knees servicing the sexual desires of strangers while wearing sexy, feminine lingerie. But, somehow I was linking it to my relationship with Tina. I felt OK as long as she was close. But interacting with this man felt degrading. I knew I needed to work that out if I could continue along this path.