Halloween Role-play with Work Wifebyhermes25©
Several years ago I had an opportunity to go out of town with my 'work wife' over the Valentine's Day week. Both of us had been experiencing rough times with our spouses, despite our best efforts, and neither of us had sex in many months.
When we arrived in Minnesota for our class, I realized I had forgotten to pack underwear. Gina was delighted to help me shop for some boxer shorts, and we also wound up buying each other some fun Valentine's Day underwear. A little modelling for each other led to some hot and passionate sex for the rest of the week.
We discarded the evidence of the holiday underwear and went back to our separate lives. We still worked closely together, and we tried to live by 'what happens out of town, stays out of town'. But every time I saw Gina, I was reliving our sexy week together, and from her sly comments and glances, I knew she was too.
Now, eight months later, Gina needed to go to a conference in a Chicago suburb the week before Halloween. She brought it up to me, smiling and suggesting I might want to attend as well. I thought it over a lot. The conference was about things that were my responsibility at work, and I had attended a similar one five years ago. I mentioned it to my boss, and he agreed it would be good for me to attend too.
We rented a car and drove to the conference on Sunday afternoon. The air was full of sexual tension, with neither of us coming right out and saying anything about sex. It was a long ride.
We got to the hotel and went to our rooms. I did remember to pack underwear this time, and brought along the boxers that Gina had helped me pick out. We met up a few minutes later to go out to dinner. We found a nice place for dinner, and along with some wine, loosened up quite a bit. We reminisced about our last trip out of town together.
"I'm wearing boxers you helped me pick out last time. Guess which ones."
"Hmmm, the white with green stripes?"
"Lucky guess! What are you wearing underneath?"
"You'll just have to be a good boy tonight and maybe you'll find out...", she replied coyly.
We had intended to see a movie after dinner, as the 'date nights' that we had done in February. However, the week before Halloween, all that was playing were slasher flicks or children's movies. As we left the restaurant, we drove past a used clothing thrift store, with a big sign, 'Your Halloween Headquarters'.
"Hey, do you want to stop here and walk around? I like looking through the costumes around Halloween."
"Sure, sounds like fun."
We pulled into the parking lot and went inside. They had several long rows of wild clothes, some official costumes, and others just weird donated clothes. We had fun walking around and pointing out different costumes.
I held up a doctor's long white coat and leered, "Hey, want to play doctor?"
Gina laughed, and replied, "Are you a full-service doctor? It's been a long time since I've had a thorough examination."
"Why, yes, Mrs. Wilson, I'd be glad to offer my services."
"Well then, Dr. Miller, I had better find a nice outfit to wear to my appointment."
I kept the doctor coat, and we walked around looking at the other clothes. I added a patterened hospital gown, and Gina found a 1950's-era floral house dress. "This looks just like something June Cleaver would wear!" It was bluish, with a collar and buttons on top, down to a pleated skirt on the botton. June would wear this with pearls while preparing dinner for Wally and the Beaver. "I think I'll take it. I better find some accessories."
Gina found some a cheap necklace with big blue plastic beads. "How retro is this? Let's see what else will complete the outfit."
We walked around the store, and Gina found some matching shoes, then stopped by the lingerie section. There were lots of old-fashioned bras. She picked up a big one with stiff material and pointed breast cups, and laughed, "I'll bet this is what the well-dressed woman wore in the 50's."
I always thought that old-fashioned lingerie was unattractive, but with the 50's role-play we were starting, it suddenly seemed sexy. "Don't forget the granny panties", I joked.
"Always the panties with you. You know, women just call them underwear."
The store had several individual panties hanging from the racks, but nothing that wasn't too used, or in her size. On the end of the aisle, I spotted several packages of clearance panties, and pointed them out to Gina. She came over and found a three-pack of nylon full-cut underwear, in light blue, pink and yellow. "I can just imagine June wearing these too! Now, Dr. Miller, we need to find the rest of your outfit."
"What do you mean, men wear almost the same styles today."
"Oh, you guys don't know anything! If we are going to look the part, we have to find the right clothes."
Gina walked me through the mens section and found some ugly tan polyester pants. "Now these look like 50's style pants!" After a little more searching, she found an old white long-sleeve dress shirt and an old-fashioned tie. "There, Dr. Miller, you'll look like a proper 1950's doctor. Now for the final touches."
Gina walked over to a small section of men's underwear, and held up a pair of red and white striped boxer shorts with a yoke front and grippers. "My dad used to wear underwear just like these. Are they your size?" They were, so I added them to my pile of clothes. We couldn't find any vintage a-shirts, but Gina agreed that my a-shirts and socks would have to do.
We checked out and drove back to the hotel. "That was really fun! I've never shopped for vintage clothes like that before."
"Yeah, Dr. Miller, you're fun to shop with. Now we have to get into character for my appointment."
We went to our separate rooms to change into our costumes. I pulled off all of the store tags and took off my clothes. I left on my a-shirt and black dress socks, but swapped my boxers with the retro yoke boxers. I put on the tan pants, white shirt and vintage necktie. My black dress shoes and the long white doctor coat completed my outfit.
I cleaned up the room a bit and brushed my teeth, waiting for my next 'appointment'.
A short while later, there was a knock on my door. I opened it to see Gina looking stunning in her floral dress, matching shoes and blue bead necklace.
"Hello, Mrs. Wilson, come on in."
"Hello Dr. Miller. I'm sorry I'm a little late." Gina walked into the room.
"Not at all, Mrs. Wilson. You are my last appointment for the day, and I'm afraid my nurse had to leave early. But I have plenty of time to spend with you."
I admired how naturally she flowed into the room, as if she wore dresses like that all the time.
"If you could please remove your dress and put on the gown. You may leave on your underclothing. I'll leave you alone for a few minutes."
"Thank you, Doctor."
I walked to the room's bathroom, and listened as I heard Gina taking off her dress. I waited a few minutes, and lightly knocked on the wall.
"Are you ready, Mrs. Wilson?"
"Oh, yes, thank you."
I talked back into the room, to see Gina sitting on the edge of the bed, wearing her necklace and hospital gown. Her dress was neatly laid across the couch.
"Now, Mrs. Wilson, what seems to be the problem?"
"Well, Doctor, I just don't seem to be feeling very energetic. I haven't felt very amorous to my husband in months."
"Do you have any pains or aches?"
"No, just feeling overall blah and unappreciated."
I took my hands and gently laid them across her neck, feeling her warm soft curves. "No swollen glands"
I ran my hands inside the neck of the gown. "My stethescope isn't working. Do you mind if I listen to your heart with my ear?"
"Not at all, Doctor."
I untied the top of the gown and let it slide off her shoulder, exposing the vintage bra. It was strangely erotic, seeing such old-fashioned lingerie. I placed my ear over her heart, adjusting the bra cup a bit to expose more skin. Her heart was beating fast, and I could hear her breathing speed up.
"Everything seems to be ok here, Mrs. Wilson. Your heart rate is a little fast."
"It just may be the situation, Doctor. It's been a very long time since any man has seen me undressed, especially my husband."
"I understand. I'll continue with the examination." I bent down and picked up her leg, flexing the knee. "Any joint pain or problems walking?"
I did the same with the other leg, moving my hands up Gina's thigh. "Any hip pain or issues?"
As I raised her leg, the gown fell back, revealing the light blue nylon granny panties Gina was wearing. I could not believe how hot she looked! I immediately felt my cock harden in agreement. I had always been turned on my skimpy lingerie, and thought old-fashioned underwear was ugly. However, the role-play opened up new avenues for me. The crotch of the panties was a darker blue, wet from her pussy juices.
I rubbed my hands slowly along her thighs, first on top, then inside, moving them slowly closed to her pussy. "Any tightness of the muscles here?"
Gina was starting a low moan and replied, "No Doctor. That feels really good. I'm starting to feel some of the dullness wearing away."
"That's really good. Maybe all you needed was some increased circulation and muscle relaxation."
"That sounds wonderful, Doctor."
I continued the slow massage of Gina's thighs, lifting the gown so I could see more. I brushed a hand against her crotch and felt the dampness. Gina moaned.
"I will need to examine your pelvic area to make sure everything is healthy. Could you raise your bottom so I can remove your panties?"
"Of course, Doctor."
Gina sat back on the bed and pulled up her feet, placing them on the bed as well. Then she lifted her bottom. I reached up to her waist and pulled down the granny panties, then worked them over each leg.
"Please put your legs here so I can continue the examination." I helped place her feet on the edge of the bed, parting her legs so I had an open view of her magnificant pussy. I could see the lips glistening with wetness.
"You may think this is strange, but I can usually detect conditions such as a yeast infection just by smelling." I raised her damp panties to my nose and took a deep breath. Her musky aroma lingered and I felt my cock twitch again with arousal.
"So far, things smell normal. But to make sure, I will also use my sense of taste." I ran my tongue across the damp crotch of her panties, tasting the salty wetness.
"Is that really accurate Doctor? I would think you would have to examine the real thing to be certain?"
"That was just a preliminary test, Mrs. Wilson. Of course, I will need to do a thorough examination to make doubly sure. Your well-being is my top concern."
I dropped her panties to the floor, and bent down to look at her open pussy. I brought my face closer, reveling in the hot sex smell. I lightly licked her wet pussy lips and Gina groaned out loud.
"Oh Dr. Miller! That feels so good!"
I kissed her wet pussy, moving my lips around for more contact. I alternated licking, kissing, and sucking on each swollen pussy lip. My tongue darted inside her relaxing pussy, as more of her juices leaked out.
I moved my tongue up the lips and encountered her hard little button of a clit. Gina jumped a little and let out a low groan. "Oh, Dr. Miller! What are you doing down there? I feel so tingly!"
I lightly sucked on Gina's clit, running my tongue in tiny circles around it, first fast then slow. I could feel her thighs starting to tremble.
Sudenly I felt hands around my head, pulling me up. Gine grabbed my necktie and pulled me up to look in her face. "I think I want you to fuck me, Dr. Miller! Fuck me with your big cock!"
Gina reached down and undid my belt. I felt my polyester pants slide down my legs. She grabbed my hard cock through my boxers and gave a squeeze. "You are so big and hard, Doctor. I want you to fuck me with this!"
Grabbing the waist of my yoke boxers, Gina pulled and the grippers opened, the boxers sliding to the floor too. She grabbed my cock and pulled it toward her waiting pussy. My shirt tails got in the way, and Gina grabbed the front of the shirt, tearing it open and sending buttons flying. "I've always wanted to do that!"
I pulled up the rest of her hospital gown as Gina guided my cock into her pussy, the hot wet lips parting easily as I slid inside.
"Oh, yes, Dr. Miller! Your cock feels so good inside me! Fuck me!"
I slid my cock in and out, slowly, then picking up speed. She was so wet and warm. I could feel her muscles clamping around me as I pumped.
"Mrs. Wilson! You are such a sexy woman!"
After a while, my legs began getting cramped from the awkward position. "I think we need to change positions."
I withdrew and helped Gina stand up. I turned her around to face the bed, then undid her gown, letting it drop to the floor. She stood there, in her vintage bra and blue bead necklace.
I took off my doctor coat and torn short, and kicked off my shoes and pants around my ankles. I kicked off the open boxers and stood there with just my a-shirt on.
I helped Gina raise her right foot on top of the bed, opening up a clear path to her wet pussy from behind. I could see drops of her juice clinging to the fine hairs of her pussy. I approached Gina from behind, guiding my hard cock into her pussy.
Gina groaned, "Oh God, Dr. Miller! Yes, fuck me!"
I grabbed Gina's waist and pulled her toward me as I pumped. She bent forward and put her hands on the bed for balance. It was so sexy watching her in that vintage bra and necklace. From this angle, I could penetrate deep into her pussy.
Reaching up Gina's back, I found where the bra was fastened. I struggled while trying to unclasp the three hooks. "Yeah, I had a hard time getting that connected myself! How did teen boys in the 50's ever learn how to unhook these?" Gina broke character and laughed.
Eventually I opened the bra and helped it off her. I reached my hands around and stroked her unsupported breasts. Gina's nipples were hard little balls, and I tweaked them as I continued fucking her from behind.
"Dr. Miller! I'm going to cum soon! I want to feel your hot sperm. Shoot your load in me, please!"
I couldn't hold it much more myself, and pumped a few more minutes until I felt her legs trembling and I let loose.
"Oh God! Aaaaaaaaaaaaaaaaaahhhh! Yes! Fuck me!"
I pumped as the cum spurted out of my cock into Gina's hot pussy. Thrust after thrust, the cum shot out of my throbbing cock. Her lips got so slick as I slid in and out. I felt our combined juices starting to leak over my balls.
I pulled out and we collapsed to the bed, laughing.
"That was so hot! I don't think I'll be able to walk for a week! I don't think I was ever fucked like that before!"
"That was so wild, with the costume play. Much easier to try new things by being someone else. And I can't believe how sexy you looked in that old bra and granny panties!"
"Those panties were actually very comfortable. I may decide to keep them, even if we don't take the rest of the clothes home."
"What will your husband say if he sees them?"
"I don't care. Besides, he isn't interested in seeing me partially or completely undressed. He'll probably never even notice."
"Well, he's an idiot. I'd enjoy seeing you in whatever you were wearing."
"Then maybe we should go back to the Thrift Store tomorrow and find some other costumes? We've got the rest of the week before Halloween and my imagination is running wild."