A Double Date with My Wife

"They're here!" My wife Sherry called out from the living room. I did a quick fit check and adjusted my small boobs in my bra so they popped out of the top of my thin summer dress and created a nice cleavage. I teased my long hair and checked my makeup one more time.

"Crystal, hurry the fuck up!" Sherry said impatiently. "I swear now that you're a girl, you spend so much more time in front of that damn mirror!"

A quick horn tap from outside from the guys and I rolled my eyes and sighed. I opened the bathroom door and walked towards the living room. My heels clicked on our wooden floor as I entered the room and I saw Sherry peaking out the window.

"Finally, it's about time!" Sherry said shoving a purse into my hands. "I put your ID, makeup and a few other things you might need inside."

I looked the purse over. It was one of her favorite ones that I had always admired. I started to open it to see what was in it but she grabbed my hand and pulled me out the door, locking it behind us. The cool night air swirled up my freshly shaven, stocking covered legs and up my dress and over my bra and panties. Goosebumps and chills spread over my body making my nipples harden as she led me down our sidewalk towards the waiting SUV. I gripped her hand tightly as we walked trying to to steady myself in my heels and not fall on my ass. Just as we approached the SUV, the doors opened and Paul and Terry got out.

We greeted each other and Paul led Sherry to the passenger front door while Terry guided me towards the back seat. He was a big guy and I was surprised that I actually had to look upwards when I talked to him. He opened the door for me like a gentleman and I smoothed my dress down beneath me as I climbed into the seat.

"Slide over to the middle, please." Terry said with a smile. Confused I looked over at the middle of the seat then slid over. He got in beside me and placed his big arm around my shoulder and pulled me close to him so that I was sitting up against him. His rough hand on the bare skin of my shoulder sent more chills down my spine and as I looked down, my hard nipples were clearly poking out through the fabric of my bra and dress.

The inside car light was still on as Sherry turned around in the front seat and she got a very surprised look on her face. Her beautiful eyes looked me up and down, then at Terry's big arm around me, then spent a few lingering seconds on my nipples before looking into my eyes and smiling, "Comfy?" She teasingly asked with a wink. I felt the blush burning in my reddening cheeks as I nodded yes. She turned back in her seat and started chatting with Paul.

The overhead light went off and I watched our house fade away as we drove off, making memories flash in my mind from the last two years. After years of hiding it, I had finally told Sherry everything. How I had secretly been wearing her clothes and makeup. How it had been an issue my entire life and now it had come to a point where I couldn't live the lie anymore because I didn't want to live if it meant I had to do it as a man. I felt selfish for hurting her but it was my last grasp at a reason to live.

Sherry tried her best to be understanding. She gave me some of her clothes and makeup, we went shopping together. It hurt her also, she cried, we fought, we talked about divorce. I had started hormone replacement therapy and laser hair removal when she seemed to come to terms with everything and that I was sure of what I wanted.

One night during sex, Sherry was on top of me in the missionary position, her strap on buried deep in my ass as my stocking covered legs wrapped around her waist and my ankles locked behind her back. Her heavy boobs squished into mine as she laid on top of me with her lips almost touching mine.

"Yeah baby! You like my fucking cock in your pussy, don't you slut?" Sherry teased as her hips ground into me, making her cock rotate in my ass. She kissed my lips and shoved her tongue into mouth as her hand roughly squeezed my boob. "Tell me you like getting fucked!" Her warm breath teased my wet lips as she growled. Her hips pulled back making me feel every inch of the long shaft slipping from my insides until just the bulbous head was left at me opening. She slowly rocked her hips making my tight opening twitch and squeeze at her. If you want to get fucked, you have to tell me!" She ordered again then roughly slammed back into me making me gasp and dig my long fingernails into her back.

"Yes, I love getting fucked!" I cried out into her smiling mouth as her hips began a steady thrust. My trembling hands slid down her smooth back and I grabbed handfuls of her soft ass cheeks and squeezed hard as I guided her in and out of me.

Sherry sat up straight and pulled her cock out of me, my hole gaped open a few seconds before slowly closing. She grabbed my hips and flipped me over onto my hands and knees with my ass up in the air. I smiled as she spat on my hole and the warm wetness slid down my skin.

"Damn look at your fucking tits! They look awesome!" Sherry said as she reached beneath me and grabbed my boobs and pulled at them roughly. She grabbed my long hair and pulley head back, her dildo pressed against my opening, making me push back against the big head.

"Oh wow, you really need a cock inside of you don't you girly?" She teased as she slapped my hanging breast making it burn before sitting back up straight and guiding her cock back into me. I cried out as her thick dildo ripped into me making my hole spread open.

"Geeze, you're so loud!" She said yanking my hair back as hard as she could so that her mouth was at my ear. She licked my ear lobe and bit the dangling chain on my earring making it pull on me. "We need another cock here to go in your mouth! I bet you'd look so fucking cute being spit roasted by a couple of big cocked guys!"

I got chills from hearing her say that and that made my nipples rock hard and with her hand on my boob, she noticed instantly and her fingertips pinched and pulled at my sensitive nipple. "Oh my! I think she likes it!" Sherry teased while fucking me faster. Her hand left my breast and slid down my tummy, stopping to tease my cute butterfly bellybutton piercing then down to my penis making me jump as she touched it.

"Girly's little clitty is dripping wet!" She moaned into my ear as her hand teased my penis and gathered up all of the precum. Sherry pulled my hair back again and shoved her slippery fingers into my mouth. I eagerly sucked and licked her finger clean while I thrust my ass back against her. "I want to see you get fucked! I think you need to know what it's like to get fucked by a real cock and have a real man breed you and bury his seed deep inside of your soft little body."

I thrust my hips wildly back against her as she thrust into me. My dangling little boobs jiggled beneath me as the slapping sounds of our bodies echoed in our bedroom. Sherry's slippery fingers danced firmly over the head of my penis just like she does when she's fingering her own clit, making my knees start to shake as I felt the warm tremble begin inside me.

"Tell me you want a real cock and I'll let you cum in my hand and I'll let you clean it up!" Sherry whispered in my ear as her fingers furiously flicked my head.

"Oh fuck yes, I want a real cock to fuck my pussy! I want to be creampied and used!" I cried out as the top half of me fell to the bed, my boobs squishing beneath me. My penis twitched and my body convulsed as spurts of hot clear cum pooled into the palm of my wife's hand.

Sherry pulled her dildo from my gaping ass and my trembling knees weakened and fell to the bed. Her pretty hand came to my face, her red painted fingernails glistening with cum. My heart pounded as I gasped trying to catch my breath. She tangled her free hand into my long hair and pulled my head up to her other cum filled hand. I stared into her eyes while I licked and sucked her hand and fingers clean until it was all gone. "Good girl!" Sherry said slapping my ass.

Fast forward to now and here I am, on my first double date with my wife and two strangers that she found online. I looked up between the front seats and saw Sherry lightly petting and playing with Paul's arm hair while he drove. I knew my wife very well and that was always a sign of her horniness and I could imagine her bald pussy was now dripping into her panties.

"I want you to suck my cock." I faintly thought I heard Terry say next to me, bringing me back to reality. My eyes got huge and I blushed as I looked at his crotch the up at his eyes. My mouth literally watered and I had to swallow.

"You want what?" I nervously asked, my voice so shaken I heard it trembling. I cleared my throat and shook my head, "I'm sorry what was it you wanted?" I asked leaning in closer to him.

"I said it's almost seven o'clock, we'll get there just in time." He said smiling.

"Oh... Ok..." I said blushing and realized that I was just about to go down on him in front of everyone if he told me too. His big hand squeezed my shoulder and he pulled me close to him again making me feel so small. As I settled in next to him to get comfortable I realized I didn't know where to rest my hand, so I pretended to reposition myself so that I could put my hand on his thigh without it seeming too obvious. That was when I realized his long cock was stretched out alongside his leg and two of my fingers were actually resting on it through his pants. He leaned back and stretched his leg out as much as possible giving my full access.

I looked up at Terry who just sat smiling and nodded down toward his lap. I smiled and looked down to see the long ridge going alongside his leg. In the passing street lights I could see my purple glitter nails as they slowly slid up and down the length of him. I felt the outline of his thick mushroom shaped head and had to swallow hard again. His cock was way bigger than mine had ever been and now mine had shrunk considerably because of the estrogen and testosterone blockers.

I looked up to Sherry again who was still teasing Paul's arm. I suddenly felt naughty and empowered knowing that even though my wife was clearly flirting with Paul while I was sitting behind her, I had taken it a step further by teasing the head of his cock through his pants in the darkness.

"We're here!" Paul said as the car suddenly came to a stop and turned off, the inside lights came on and blinded me so I had to squint as my eyes adjusted. As they came back in focus I saw Sherry had turned to look at me and she was staring at my hand on Terry's thigh. I quickly pulled it away embarrassed, making her laugh and we all got out of the car.

As we stood in the parking lot, Terry went over to talk to Paul. I saw them looking back as they talked and I could only imagine that he was telling Paul how I was playing with his cock on the way here.

"I put your ID in your purse." She said motioning to the purse I had nervously clutched in my hands.

"Oh wow, thanks! I hadn't even thought about it!" I giggled and opened the purse. As I looked in, I saw makeup, my wallet, condoms, lube and a few other little girly items. "You thought of everything didn't you?" I said laughing at the condoms.

"Yeah, well, I wasn't sure if you wanted condoms because I know how much you're looking forward to getting creampied!" Sherry explained very loudly making me grab her hand and shush her. I heard the guys laughing, they had to have heard her. "Oh calm down," Sherry said rolling her eyes and laughing. "I saw your little hand on his cock! I don't think it's going to shock him that you have condoms and lube." She said teasing me and laughing.

"Oh my fucking god, come on!" I said grabbing her hand in embarrassment and walking towards the entrance of the club, the guys followed closely behind us.

Once inside, Sherry and I found a table while the guys went to get drinks. "You look really pretty!" Sherry said looking me over. "I'm so proud of you! I never thought we would be happy again but I think this was the right step for us." She said taking my hand in hers and looking at me in a way she hadn't in years.

"You're absolutely beautiful!" I said looking her deep in the eyes. "I don't think I'd be alive if it weren't for your support." I said tearing up.

"Oh shut the fuck up!" Sherry said dabbing at my tears with a napkin. "You'll ruin your whore makeup!" She said making me bust out laughing. She always knew how to make me feel at ease.

Just then the guys appeared with drinks and the wild night carried on. We drank we danced, we flirted, it's was an amazing night. As the club closed, we found ourselves very drunk and standing outside in the parking lot.

"None of us should be driving." I said looking at the car.

There's a fucking hotel right there," Sherry said pointing across the road. "We'll get a room, then drive home when we're sober!" Sherry said as she wrapped her arm around Paul's waist. Terry grabbed my hand and we all walked over to the hotel.

I was so happy to get into the room. I rushed over and sat on the edge of the bed and took off my heels, my feet were killing me! Sherry sat down next to me and took hers off too. We were looking down at our feet talking about how they hurt and Sherry tapped me on the shoulder. I stopped talking and looked up to see Paul and Terry standing in front of us with their pants down around their ankles and their cocks out. My eyes got huge and I couldn't help but giggle as Terry stepped forward and his big cock bounced and swayed as it got closer and I reached out and grabbed it in my hand.

I shut my eyes and closed my lips around his shaft as my tongue flicked and swirled at his head inside my mouth just like Sherry had taught me to do with her strap on. I brought my hand up and gently lifted and squeezed Terry's heavy ballsack. His big hands went into my hair and pulled me against him as he pushed further into my mouth making me gag and relax my throat. I had spent many times with Sherry's dildo in my throat. Terry's cock was bigger, but I was still proud of how well I was doing. I could hear Sherry glucking down on Paul's cock next to me.

After a while, Terry pulled out of my mouth and went over to my purse and grabbed the lube and condoms. Paul pulled out of Sherry's mouth and she kissed me deeply, shoving her tongue into my mouth. It was such a sexy, precum slippery kiss. Sherry had me stand up and told Paul and Terry to remove the nightstand from between the two beds and push them together. I watched as they quickly did as they were told, their naked hard cocks bouncing around as they did made Sherry and I both giggle.

The two beds were becoming one as Sherry and I undressed each other. As we stood nude in front of each, Sherry looked down and smiled as she leaned forward making our nipples touch then our soft breasts slowly pushed into each other.

"I never would have imagined that I'd be this excited to share cocks with my pretty little husband!" Sherry whispered into my ear as the guys finished moving the beds. "Seriously! Feel my fucking pussy!" She said grabbing my hand and placing it against her hairless mound. I smiled as my fingers found the gooey mess she was talking about.

"Holy fuck!" I whispered looking at my hand glistening with her juices. I licked my finger than grabbed her and led her to the beds they had just finished sliding together. "I have to fucking taste you, get on top of me!" I said lying down on my back. Sherry quickly climbed on top of me in a sixty nine position and placed her swollen pussy inches above my face. I had never seen her so red and puffy before. As I stuck my tongue between her folds, her heat radiated onto me, she was literally in heat as she lowered her pussy onto my mouth and cried out when my tongue found her clit.

Paul appeared behind Sherry and above me. I watched as his cock slowly entered my wives aching pussy an inch away from my mouth sucking her swollen clit. I heard Sherry gagging and I knew she was sucking Terry's cock. I tilted my head back and Paul's big balls landed right in my mouth so I licked and sucked, making him moan and pull out of Sherry long enough to stick his cock in my mouth. Sherry's pussy juice was all over his cock and that made me enjoy it more. He put it back inside Sherry making her moan as I went back to licking her hard little clit.

I felt Terry's rough hands on the insides of my knees as he lifted my legs and spread me open. I heard Sherry gasp as he pulled his cock from her mouth then I felt his tip, soaked with my wife's spit, press against my opening. "She doesn't want you to use a condom!" I heard Sherry whisper to Terry. Sherry's hands went beneath me and she grabbed my ass cheeks and opened me up. She put my little penis in her mouth making me moan and I knew she had a good close up view of Terry's cock going into my ass.

I cried out loud into Sherry's pussy as his cock slowly impaled me. "Oh for fucks sake, now I remember why we're doing this!" Sherry said laughing as she got off of me and told me to get on my hands and knees. I did and Terry quickly put his cock back into making me yell again and Sherry grabbed Paul's cock and shoved it into my mouth. My whimpers muffled by the cock in my throat, Sherry sat back and admired the situation. "I told you you'd look fucking sexy with two cocks in you!" She said with her fingers working her pussy.

Paul pulled out of my mouth and pounced on top of Sherry and shoved his cock deep into her pussy. Her legs spread open and I could hear him sloshing in and out of her wet pussy next to me as Terry slammed into my ass over and over. After a couple of minutes, Terry began to grunt and his thrusts became more jagged, I knew he was about to cum inside of me.

In his lasts thrusts, he threw himself into me so hard he fell on top of me making me collapse beneath him. He grabbed handfuls of my hair and pulled as he grunted into my ear through clenched teeth. I felt his cock convulsing inside of me then spurt after spurt of hot sticky cum hit my insides. I laid pinned beneath him, his cock twitching inside of me, pumping every last drop into me.

I looked over at Sherry who was in the missionary position, her stockinged legs bounced in the air as Paul drove his cock into her wet pussy. Sherry looked over at me pinned beneath Terry, he was still rocking his hips into me and had me pinned down so I couldn't move. Her eyes were glossy and as Paul began to cum, her eyes rolled back into her head then shut. After he emptied himself into her, he pulled out and went to the bathroom. Sherry's used pussy was spread out, swollen and purple and I could see the cum inside her began to drip out.

I squirmed beneath Terry and begged to be let up. He rolled off of me and I scurried over to my wife and crawled up between her spread legs. She let out a soft whimper when my mouth began licking and sucking her pussy. I had never seen it so swollen before and she jumped at every touch. I began working her clit, slowly at first then faster until she was crying out loud and juices were squirting from her.

The next thing I knew, the light was turned off, Terry grabbed me and pulled me up against him so I was the little spoon, Sherry and Paul were across from us and she reached out and held my hand as we all fell asleep.