More Role-play with Work Wife

My work wife and I were spending the week before Halloween at a conference in a Chicago suburb. We were both lonely and unhappy in our marriages, and had hooked up around Valentine's Day before this conference came up.

We were feeling horny, and had stopped at a thrift store on a whim and bought some vintage clothes to dress up and role play a doctor/patient in our hotel room last night. It was such an exciting and arousing game that we both felt so alive.

After showering, we slept naked in each other's arms all night, then had another brief round in the morning before we had to get ready for the day's events. Gina threw on her old clothes and was getting ready to go back to her room for a shower and clean clothes when she came up to me holding a pair of the pink granny panties we had bought last night for our role play.

"I think you should wear these under your dress clothes today, " she purred. "I want to imagine you in them all day, and maybe you can model them for me tonight."

I smiled. "Sure. I've never worn panties before, but it sounds like fun. Maybe you can wear something of mine under your clothes? I have some tighty whities or boxer shorts."

I walked over to my suitcase, and rummaged around to pull out my clean underwear. "Here, any of these interest you?"

Gina looked through my stack of underwear, and held up a pair of white boxers with little geometric shapes. "I think I'll wear these under my skirt, " she giggled. "Ok, off to shower and get dressed. I'll meet you for breakfast downstairs in an hour."

She left and I showered and shaved. I put on the pink nylon granny panties and instantly got a hardon. The silky material felt so good on my cock and balls, and didn't provide much support as I made a huge tent in the loose material. It was going to be interesting to keep my cock tucked in all day in my dress pants.

I met up with Gina for breakfast and we discussed our day's activities, as we were going to split up to attend different events. "I am so looking forward to being with you tonight," Gina told me. "We'll have to think up another game to play."

All through the morning, as I attended various presentations, my mind was wandering and fantasizing about our role play last night and what might happen tonight. Of course, my cock was throbbing as it tried to escape the nylon material, and I had to walk with my handouts in front of my crotch to hide the constant tent.

We met up for lunch, and Gina whispered to me, "I am so wet right now. Your boxers feel so open on my pussy that it almost feels like I'm not wearing anything under this skirt."

I grinned. "What do you want to do tonight?"

"Um..." she hesitated.

"What?"

"No, it's ok..."

"No really, tell me. Now I'm curious," I smiled.

Gina blushed and hesitated again. Then she seemed to make up her mind, and she leaned in to whisper to me, "I want to be a man. These boxers got me thinking. I want to dress up as a man and make love to you. Is that weird?"

I was surprised, but replied, "No. I think that is really hot, and would be fun to play with you."

"Really? I have one more idea. My husband would never want to try new things, but I always wanted to wear a strap-on. Is that too kinky?" She looked away quickly.

Wow! I didn't expect that. "Um...well, I guess not. I've never seen one personally, but they seem pretty popular." I thought it over. "Sure, let's see if we can go shopping again tonight." I grinned at her.

Gina seemed embarrassed, but laughed and said, "It's a date! You take me to the nicest places!"

We laughed, and split up for the afternoon sessions. I was harder than before thinking about Gina in a strap-on. I guess that meant I was going to explore some new adventures too. I wasn't sure how I felt about that, but everything with Gina was intimate and open, and I trusted her to be discrete and safe.

We met up again for dinner, and Gina told me she had searched an internet kiosk on break and found an adult toy store on the edge of town. We decided to drive past it on the way to find a restaurant and check it out. The store didn't look too bad, so we stopped at a restaurant for dinner and to get our courage up.

Throughout dinner we danced around the idea, and flirted quite a bit and I found myself getting very hard again.

"I am so wet, " Gina shared. "I think your boxers are soaked." She glanced around the restaurant, and since we were relatively secluded, she lifted her skirt and showed me. Gina was wearing my white boxers with little geometric designs, and I could see how the crotch area was slightly darker and glistening from all of her juices.

"I am so hard, " I whispered. "These panties keep rubbing against my cock and driving me wild!"

"You and your panties! You do know we just call them underwear, right?" she smiled.

We paid the bill and drove to the adult store. The store was brightly lit and looked relatively new. They had a lot of DVDs and magazines, as well as toys and lingerie. There were two other people browsing, a guy by the gay movies, and a woman by the bachelorette party favors.

We wandered around until we came to the strap-ons and dildos. "Wow, how about this?" Gina asked, as she pointed to a huge 16" black dildo called the Exxxtreme Dong.

"That looks like a pain in the ass, " I countered.

"I'm kidding!" she replied. "I was thinking of starting small..."

"Well if you want to put it where I think you do, I hope we can start small..."

"This was my fantasy, but are you sure you're ok with it? I don't want to hurt you. You just get me so horny and hot. If you want, we can just play around and don't have to do any penetration..." Gina trailed off.

"To be honest, I don't know what to expect. But it makes me excited seeing you get excited, so if we play slow and gently, I am up for trying new stuff with you. But I'd recommend starting small and using lots of lube, " I whispered.

Gina agreed, and we looked around until we found a 6" rubber strap-on cock that didn't look too thick. We had to find compatible lube, and weren't sure what to look for. Gina's newfound courage took over, and she asked the clerk for her advice, who recommended a brand. The clerk told Gina, "Be sure to let him know who's the boss", and gestured toward me. I blushed, and they both laughed.

We drove back to the hotel, and Gina had fun stroking the tent in my pants along the way. "I can't wait to play with this guy!"

We went back to my room, and Gina said "Let's get you ready." She undressed me, leaving on the pink nylon panties. Then she helped me put on the old-fashioned pointy white bra that she wore last night, as well as the June Cleaver dress and necklace we picked up at the thrift store. I was a little bigger than Gina, but the dress fit good enough. She took out her lipstick and put some on me, then a little other makeup and exclaimed, "You are so pretty!"

"Is that ok if I wear some of your clothes?"

"Sure, help yourself."

Gina took my dress pants and shirt, and got some clean boxers, an a-shirt and dress socks out of my suitcase. "I need some dry boxers - I'm afraid the ones I'm wearing are all wet now." She winked at me.

Gina went into the bathroom and changed clothes. She came out a little while later, smiling and walking a little funny, as I noticed a tent in the dress pants. She was wearing the strap-on under the pants.

"Hey, little lady!" Gina exclaimed. "You're looking mighty fine. Why don't you come over here and sit on my lap, and we'll talk about the first thing that comes up?"

She sat on the couch, and I laughed and walked over by her. "Yes sir, " I blushed.

I say across her lap, and she leaned in to kiss me. This was strangely arousing, and I kissed back, getting into more character.

We made out for a while, then Gina ran her hand across my breast, feeling the bra under the dress. "Those are some nice titties you have!"

I looked shyly away. "Would you like to see them?"

"Yes I would!" Gina reached around and unzipped the dress, and helped pull the top down to my waist, exposing the old-fashioned bra. She ran her hands across my breasts and sides, then slid the left strap off my shoulder and peeled the bra cup down to expose my nipple.

"Mmmmm, very nice, " she whispered as she took my nipple between her finger and thumb and tweaked it. I was surprised at how hard my nipple was, and how electric that felt. I moaned a little, as she pinched and twisted it.

Gina leaned over and took my nipple in her mouth and gently kissed it. I've been kissed there before, but it never felt this tingly. I moaned louder as she began sucking on the little nub.

She lowered the right strap and exposed that breast, then reached back and undid the bra and slowly removed it. Gina alternated between tweaking and sucking on my nipples, as I sat on her lap.

After a while, she went back to kissing me on the lips, warm and open. I felt her hand slide up along my thigh and under the dress until she reached my cock. She gently caressed my balls and shaft in the panties, rubbing the nylon material across my skin. I was so hard I almost shot a load right there.

Gina helped me stand up, and she slid the dress down around my ankles and I stepped out, wearing nothing but the necklace and pink granny panties. She led me over to the bed, as I kissed her and started undoing her necktie and unbuttoning her dress shirt. I slipped the shirt off her shoulders and down to the floor, enjoying the view of her in my a-shirt, her breasts firm and nipples visible through the ribbed cloth.

We kissed some more, and I undid her belt and opened her dress pants. I reached inside, and felt the strap-on dildo sticking through the fly in her boxer shorts, and I caressed it.

I had never been with a man before, and even though this was a rubber cock, it seemed so realistic as I stroked it and kissed Gina. I kneeled down in front of her and slid the dress pants down to her ankles and helped her step out of them. I took off each of her dark dress socks, then looked up to the hard cock sticking out of her light blue boxer shorts.

I took the rubber cock in my mouth, and began sliding it in and out, reaching around to caress her ass cheeks through the boxer material. Gina moaned and ran her hands through my hair, guiding me. It was so strange giving a blow job like this, but it was so arousing.

I reached up the boxer leg, almost expecting to find some balls, but the strap-on was high enough that Gina's wet pussy was accessible. I gently slid my fingers in and around the pussy lips, slick with her juices and so soft and swollen. Gina moaned loudly with delight.

I continued to suck her rubber cock and massage her moist pussy, working two fingers in and out. Gina started moving her body up and down in time with my thrusts. She gently pushed my head away and I pulled out my fingers. "Oh my god, that felt so good!" she exclaimed. "Your turn."

Gina led me to sit on the edge of the bed. She kneeled in front of me and kissed the head of my cock through the nylon panties. She continued to suck the tip into her mouth, getting the material wet and increasing the sensation. With one hand, she began massaging my balls through the silky material, while the other hand roamed around, searching for the waistband to pull down and free my raging hardon.

As my cock burst out of the panties, Gina deftly slid it into her mouth, sucking and running her tongue along the shaft. She continued to massage my balls through the nylon material, pulling me in and out of her mouth. The sensations were overwhelming, and I could barely contain myself.

Gina sat up and asked, "Are you ready for the next step?"

I swallowed, and replied, "Be gentle with me."

"Yes, baby."

Gina pulled down the panties and slipped them off my right leg, leaving them around my left. She guided me up to the bed and turned around on my hands and knees. "Good girl," she murmured.

She massaged my ass cheeks, then slowly spread them, and leaned in to lick my hole. I was startled, but she held on firmly and repeated the lick. Over and over, she licked and massaged me ass, relaxing me. I had never been played with down there, and the sensations were new and arousing. My cock was rock hard and throbbed along with Gina's tongue strokes.

Gina stood up and walked to the counter to get the lube. I watched as she read the directions, then liberally rubbed some on the shaft of the strap-on, still protruding from the light blue boxers. She returned to the bed, and squirted some on her fingers, and slowly rubbed it across my sensitive hole. Her fingers slid across the rim, and I felt one slip inside. She rubbed in and out, warming and relaxing me.

"Ok, baby, here I go, " Gina started. I felt her align the head of the dildo against my hole and firmly push. Slowly the pressure built up and I felt a pop as the head was inside. It hurt, but was manageable. I grimaced and tried to bear down, and she kept pushing against me, slowly inserting the 6" shaft. "Are you ok?"

"Yes," I grunted. "It hurts so good..."

"Ok, let me know if it's too much..."

Gina kept pushing, slowly stretching me, while rubbing my ass cheeks and pulling me back to her. I could not believe the flush of sensations - pain, pleasure, arousal.

"Oh yeah, fuck me!" I blurted. "Give me your seed!"

Gina was all the way inside now. I could feel her thighs against my ass. She had her hands around my waist and was pulling me back as she thrust forward. In and out.

"Take it, baby! Take my cock!"

"Oh god, yes! Fuck me!"

This roleplay was so intense. I really felt like a woman, complete with my necklace and pair of panties still around one leg, as a man fucked me doggy style with his big cock. I was not expecting this when I woke up this morning.

Gina fucked me for what seemed like forever, and I am surprised I did not shoot a load with all of the pressure. It was so intimate and vulnerable and embarrassing and sensual. I didn't know what I was missing.

Finally, she pulled out and told me, "I need you inside me - right now!"

Gina pulled off the boxer shorts and laid down next to me. I got up and started trying to insert my cock into her wet pussy. It was awkward with the strap-on, but more so to seem like I was fucking a guy. She undid the straps, and I helped to get the strap-on released, then she pulled me up and on her tightly, as I slid my engorged cock all the way inside her pussy.

We thrust in and out and in no time Gina blurted out, "I'm coming! Don't stop! Fuck me! Faster!"

I pushed in harder and faster, my cock overloading and tingling. I could feel the sperm welling up inside me.

"Aaaaaaaahhhhhhhhhhh!" Gina cried out. "Oh god! Oh, oh, oh!"

I shot my load - what seemed like gallons of cum. I don't think I ever shot that much. It kept spurting inside her, and I could feel her pussy getting slicker as I pumped.

"Oh baby!" I panted. "That was so good! You are so hot!"

We collapsed together, my cock still inside, but getting limp. She was still wearing my a-shirt and it was drenched with sweat. We laid like that for a while, catching our breath and letting our muscles relax.

"That was so wild!" Gina exclaimed. "You are so adventurous and you get me so horny!"

I could feel my cock getting ready to plop out of her gooey box.

"Eat me out, baby! Don't let that spunk go to waste. Lick me clean."

I grinned and pulled out. I quickly stuck my head between her legs and began licking up the flood of cum and pussy juice that gushed out. Gina moaned as I dipped my tongue between her swollen lips and lapped up the spunk. My cum tasted so earthy and salty as I licked her clean.

Gina started squirming and moaning louder. 'I'm gonna cum again!"

I sped up my licking, sucking on her extended lips and running my tongue across her enlarged clit. She was quaking faster now, groaning and arching her back.

Suddenly, she squealed and pushed my head away. "Aaaaaahhhh! Oh god!" I watched her pussy open and close, and another gush of cum oozed out. Gina let out an exhausted sigh and went limp.

"Come here and let me taste," Gina purred. I climbed up by her and she gave me a warm open kiss, touching her tongue to mine and sucking some of the cum back to taste for herself.

"I'm not gonna walk for a week!" Gina proclaimed.

"I'm not gonna be able to sit for a week!" I laughed.

"Then we're going to have to lie here and sleep for a while." And we did.