The Date

(This is a true story of my wife's and my adventures over the past summer. Even though it is true we have changed the names and the names of places to protect those involved. For those readers who have not read the other two installments, they are entitled; Oh No! and Routine Duties. Both stories detail the results of Jan's adventures in sex-role playing and how she got caught by one of the upper management personnel from where she worked. We have enjoyed reading all of the comments that have been sent to us by the readers but we want to remind you that what we have written really happened and we have attempted to tell it as close to how it happened as possible. Thank you for waiting patiently for each installment.)

I was having a hard time concentrating on the television, so I tried reading a book, which also didn't work, so I tried a magazine. When reading a magazine became impossible I decided to go into my bedroom and find something else to amuse myself. I started by looking through a drawer in my nightstand where we keep our sex toys and Jan's vibrators. I also have a small album of photos of Jan in nude poses and scantily clad in lingerie or other sexy attire. I pulled out the photo album and began looking at Jan's poses in the nude while vacationing in the Bahamas last winter. This gave me an immediate hard-on as she is probably the most sexually exciting woman I have ever seen and she looked great exposing her breasts and buns for the world to see. But this sure didn't help me pass the time while Jan was out on a date with Chuck Hassek, her john, so I closed the book and took out my cock.

I lay on the bed fantasizing about Jan and what she was doing on her date. I envisioned her riding his fat cock and this helped me to masturbate and cum all over my stomach and cock. I cleaned myself up and looked again at the clock. Damn, it was only 9:30, her date had started at 7:00 and I didn't expect her home for a couple more hours. I then went to my computer and began surfing the internet looking for hotwife sites to take my mind off from the clock and Jan's activities. It helped and finally I began to tire so I got ready and went to bed, it was 11:00. I tossed and turned and finally settled into a fitful sleep. Around 2:00 I heard Jan make her way into the bedroom and I immediately was wide awake.

"Honey? Are you awake?" She quietly called as she approached the bed. I could see her silhouette from the light outside through the curtain.

"I sure am awake, wide awake. How was your date?"

I didn't want to beat around the bush; I wanted to hear all of the nasty details. Jan climbed on top of me wearing all of her clothes. I could smell her wonderful scent; her cologne, her hair, her arousal and something different, the scent of another man. His smell was all over her. I could smell his cologne in her hair, on her skin. I was able to get my arms out from under the bedcovers and around her. I held her and she snuggled against me. My hands slid down her body and settled on her butt. I groped and squeezed her ass cheeks through the silky material of her dress. I could not feel any panty lines under her dress and this caused my stirring cock to spring immediately to hardness. Jan could feel this and giggled. We held each other for a few more minutes and then I broke the stillness.

"So, tell me everything. Did you have fun?" My voice sounded quite strained to me and I was surprised by it. Jan wiggled and squirmed for a moment rubbing against the lump that was between us.

"Oh, honey, I love you so much. Do you love me still?" She asked softly into my ear.

"Jan, I love you so much. You are my sexy, naughty little wife and I love you to pieces." I replied while trying to reach below her dress and pull the material up so I could feel her skin with my hands. She lifted up and I pulled her dress up over her butt and bunched it at her waist.

"Good because, you know I wouldn't do these things if I thought it would hurt you or us." She then lifted herself up enough to pull the blankets off from me so that she could lie down onto my naked body. My cock felt good nestled between us.

"Honey, if you don't ever want to do anything, you don't have to. I only ask you to do this stuff for our pleasure and for fun. Now tell me everything!" I demanded with a chuckle.

"Okay, you asked for it. But if you can't handle it, stop me." She warned as she began to rub her hands on my chest and then she began her tale of her night's activities.

"I left work early today, after lunch, to have my hair and my nails done special for the date. I had also had a facial while I was at it. I stopped at Victoria's Secret and purchased a lacy blue bra and G-string to look and feel extra special. I also bought a pair of dark, thigh high stockings with the lacy elastic at the top that you find so hot. I then went home to prepare for tonight. I showered, shaved my legs and trimmed my pussy hair into a sexy little tuft. I got ready and put on the slinky black dress that you picked out for me and a matching pair of high heeled pumps; you know the "fuck-me-pumps" that you like. I wore my diamond earrings and the rest of the matching jewelry and when I was finished I looked good enough for a date with any man.

When I looked at my reflection in the mirror and I had to admit that I looked like a high-class escort, not a hooker and I knew you would be pleased. I was feeling kind of horny and I was afraid that I would soak my new g-string through too soon. I took it off and put on a pair of regular panties but there was a VPL so I took them off too. I was debating whether or not to go without them. I finally decided to put the g-string back on and accept the fact that they may get wet from my arousal.

I left the house at 6:30 and I was so nervous that I was shaking. I was afraid of what might happen and anxious. I felt like I was going on a blind date, or to a court hearing. I was ready to call the whole thing off but I was so aroused and I didn't want to disappoint you that I drove down to the Black Swan. I also thought of Chuck and what would happen if I didn't show up, so I kept driving to the date. I was kind of distracted and almost ran a red light but I stopped in time. I parked in the large ramp and walked through the pedestrian bridge to the hotel where the restaurant was located on the top floor. My legs were shaking and I almost couldn't walk on the high heels. I saw no one but I was afraid I would run into someone we knew. My stomach was doing flips and I really needed a drink. I finally took the elevator up to the top of the hotel and checked my reflection in the mirrored walls of the elevator as I rode it upwards. My hair looked good but my face appeared strange to me. Then I realized that I didn't look like myself, I looked just like some high-paid prostitute. Then I realized that $200 was not really high paying so I felt almost ashamed about what I was doing.

I exited the elevator and walked unsteadily towards the two large glass doors at the entrance to the Black Swan. The image of a large swan is etched into each of the doors and the lights of the restaurant behind them causes the swans to sparkle. I almost didn't reach for the handle to open the door. I felt dread and fear creep into me. Then I straightened up, thought of coming home and telling you about my date and the hot love we would make afterwards and I went for it."

I stopped Jan's story at this point by taking off her dress. I could not keep my hands off from her hot little body and I wanted access to all of it. When she was clad only in her g-string panties, lacy bra and thigh highs she resumed her story. I began to caress her breasts through the lacy material as she sighed and then continued.

"I opened the door and was greeted by a young woman who took me to Chuck's table. As I approached it he arose and smiled broadly. He took my hand and then pulled out my chair for me and guided me to it. He then pushed it in for me and we began our date.

We had drinks and talked. Chuck is a very interesting man and he told wonderful stories that kept me entertained for hours. I laughed often and he had me feeling so relaxed I forgot my fears and anxieties. We talked about the people we knew at work and I had a great time with him. He held my hand often and at times would look into my eyes like a lover. His hands are large and strong and my hand felt tiny in his. At times he would caress my thigh or touch my knee as he looked into my eyes and talked with me.

Dinner was excellent and Chuck ordered a very expensive wine with dinner that was the best I have ever drunk. Chuck complimented me all through dinner about my work, my dress and especially about my body and looks. He even talked about my breasts at dinner when the waiter wasn't around. He said that he liked how soft and pert they were and he liked the color of my nipples. I blushed about a hundred shades of red and this made him smile at me. He was quite bold with me and often would steer the conversation around to sex. After a few glasses of wine I felt myself losing all my inhibitions and when he asked me questions about our sex life I was able to answer his questions quite honestly and openly.

"So Jan, how long have you and your husband been married?" Chuck asked while holding my gaze with his.

"Justin and I have been married 3 years." I answered him while looking right back into his eyes.

"He knows that you are out with me?" He asked his fingertips making little stroking motions on my hand.

"Yes, I told him all about our date." I was feeling a bit uncomfortable but his movements helped me relax.

"You told him about yesterday's blowjob in my office?" He asked with just a hint of dominance in his voice.

"Yes." I answered feeling a little tingle between my legs.

"He got excited hearing about it didn't he?" Chuck continued with his interrogation.

"Yes, very excited." I admitted and Chuck's fingertips caresses were making me feel more and more tingly.

"What did you tell him? Tell me what you said to him." Chuck pressed me for details.

"I told him that you called me up on the phone in my office and made me come down to your office and suck your cock." I could not believe I was telling him this at dinner. I looked around and though the room was filled with other diners no one appeared to be able to overhear our conversation. My face by this time was coloring more and more due to embarrassment and arousal.

"Did you tell him that you showed me your breasts? That you allowed me to finger you? That you came for me, like the nasty little slut that you are?" He continued to caress me as he looked straight into my eyes and asked me these questions. I was feeling myself almost panting as I spoke to him.

"Yes, I told him how I was almost naked in your office. I told him that you had your fingers in me and I told him how you made me come for you." I admitted.

"Were you having sex when you told him about this? Did it make him cum? Did you fuck him as you told him?" Chuck had a funny glint in his eyes as he asked me these questions.

"We were touching each other. No we didn't fuck, I wanted to be clean for our date. I gave him a blowjob and he came very quickly after I started." I could not believe I admitted that to him. Chuck kind of chuckled and then asked.

"It really turns him on to think of you sucking me off doesn't it? He gets off on you being with me. He will really be excited after I sleep with you tonight." Before I could answer the question, the waiter appeared with our salads. This however didn't faze Chuck and he pressed me for an answer.

"Well, Jan, won't he?"

"Yes he will." I admitted and looked away from him towards the fresh salad which had been placed in front of me.

The conversation changed during dinner and we continued to talk about Chuck's past businesses and experiences. I learned that he was a very wealthy man and had operated several large businesses in town but had changed his career after his wife got sick with cancer. She had died four years ago. He had not dated since her death as he didn't feel ready for another relationship.

We left the restaurant, arm in arm, around 9:30 and walked to the elevator to take us to his room on the 15th floor. In the elevator Chuck held me close and kissed me for the very first time. His kiss was electric and I opened my mouth and readily accepted his tongue into it. He felt so strong as he held me and his hands began to gently stroke my buns through my dress as we rode downward. He broke off the kiss when the door opened onto his floor. We walked to his room with his arm around my waist. His hand would slip down and he would gentle pat and caress my butt as we walked. I was feeling almost breathless from the sexual energy I was feeling. I don't know if it was the wine or the situation but I wanted this man badly.

I could feel my body reacting to him as we walked down the hall together. My nipples were tingling from the stimulation of the lace on the bra. My pussy was starting to moisten again and I could feel my face and chest beginning to flush bright pink from excitement. I could feel the emotional thrill of the situation throughout my body and I enjoyed the feeling.

Chuck opened the door to the room and we slipped inside where he once again pulled me into his arms. We kissed and touched one another and I could feel the growing hardness of his cock against my tummy. He felt my breasts through my dress and I could feel my arousal grow as he felt me up. We were practically dry-humping standing up when Chuck broke off the kisses and guided me toward the bed. He pushed me and sat me on the bed and he stood up and reached for his wallet.

"Chuck, I don't …" I started to protest, to tell him I was enjoying myself so much that he didn't need to pay me when he cut me right off.

"Jan, before you say it, let me say that I agree. A complete date with you is not like a quick fuck in the car. I will pay you $400 for tonight and maybe more." He smiled and handed me 4-one hundred dollar bills. I didn't reach for them right away but instead tried to finish my sentence.

"What I meant to say Chuck was that you don't need to pay me for tonight. That this can be a real date." I was hoping that he would I understand that I wanted to have sex with him, not as a whore but as a friend.

"No Jan, let's keep this strictly business. A deal is a deal and you should remember that sex with you is a business relationship." Chuck lectured me and I felt that there might be a hidden message in his words. I took the money from his hand feeling like a real whore and placed it inside of the small purse I had carried with me. I closed the purse and set it on the night stand beside the bed.

"Jan, I want you to be completely honest with me." Chuck said as he stood in front of me as I sat on his bed.

"Okay Chuck, I have always been completely honest with you." I felt strange like I was defending myself.

"How many other men have you had sex with for money? As a paid escort?"

"Just you the other night Chuck, no one else. It is just like I told you before, I was role-playing." I explained to him as he approached me closer. My sitting knees were now touching his standing knees.

"Jan, have you and Justin ever tried swinging or swapping?" He asked while placing both of his warm hands on my shoulders.

"Yes Chuck, several times." I answered while I enjoyed his touching which turned to gentle squeezes.

"I figured that. It was Justin's idea, wasn't it?" He continued.

"Yes, Chuck. I told him I wasn't interested at first but he talked me into it." He was now rubbing and squeezing me. I was really getting into the eroticism of answering his questions and could not wait for the next one.

"And now you enjoy it just as much, don't you?" He said almost accusingly.

"Yes I do, in fact I will initiate it now." I was staring to get really excited by his questions and felt good about answering them for the man who paid me.

"When you have sex with other men is Justin there watching?" He asked as he started moving his hands down to my breasts. He grabbed each one and held them up from underneath as if he were holding a piece of fruit in each hand.

"No, not anymore. He was at first but now he just waits for me at home to return and tell him everything that happened." I was starting to feel really warm and wanted him to remove my dress.

"He gets really turned on by what you tell him doesn't he? He likes to fuck you as you tell him too. He probably eats you afterwards doesn't he?" Chuck appeared to know a lot about Justin and my behavior and while this was initially exciting it began to trouble me.

"Yes he gets extremely turned on and he wants to see if there are any signs of another man anywhere on my body. He will often eat me as I tell him what we did and if the other man didn't wear a condom he loves to clean me out with his tongue. Then we will often fuck as I tell him what happened." I admitted everything to Chuck and I wondered where this was going.

"This really turns you on too doesn't it my little whore?" He asked as his fingers found my nipples through the material covering them and he began to pinch them lightly.

"Yes Chuck it does. It makes me incredibly hot." I was lost in the moment and started to sigh from his actions with my breasts.

"I knew that too, you are such a slut! Now stand up and strip for me." He ordered. I swallowed hard at his stinging words. God, I was so hot, so horny. I stood up and turned around so that he could unzip the zipper at the back of my dress. He unzipped it and stepped back. I noticed that there was a large tent at the front of his slacks.

I slipped the material of the dress from my shoulders and let the dress drop to the floor. It puddled at my feet and I stepped out of it. I was now clad only in my lacy blue bra, lacy blue g-string panties, my thigh high stockings and my heels. I unclasped the clasp on the front of the bra and pulled it from my breasts. I was now feeling the part of a paid prostitute and wanted to get down to business and get home.

Chuck was watching my face intently as I stripped for him but I also noticed that he liked to watch as the removal of each item revealed more of my body to him. I kind of shivered as I stood before him, not from cold but from the excitement of the situation. I held both of my breasts in my hands and my touch felt good as I cupped both of my boobs.

"You have nice little titties Jan, I like them. Keep going."

I uncupped my boobs and reached down to the small elastic string that encircled my hips. My fingers found it and pulled it from me so that I could pull my g-string down. It slowly slid downward and I could feel the stickiness of my secretions hold it to my pussy for a few seconds before it pulled free. I pulled them down to my feet and over my shoes. I was standing in front of my customer, my first real john, my superior from work showing parts of my body that I had not shown him before. My pussy was shaved almost entirely, save for a small little patch right above my slit. I stood before Chuck; my legs slightly parted and tossed my g-string onto the bed. I was so aroused that my hand went down to my pussy to touch myself and feel the wetness.

"Jan, your body is marvelous. I am so glad that I bought that cute little pussy of yours. Now lie back on the bed and spread your legs for me. Show me my prize." Chuck ordered me. I complied and slid back onto the bed. My head reached the pillows and I spread my thigh open for him revealing my wet and ready pussy to his eyes.

"No, use your hands. Spread yourself wide open for me."

I used my hands and spread my thighs as wide apart as I could. I was as open to this man as I had ever been to my husband. I felt wicked as I displayed myself to him.