"Oh, here's something interesting," my fiancée Angel said, browsing through the throw away paper calendar. "A local strip joint is having a Pimp 'N Ho Party Saturday night. Bikini dancers, good food, music and live entertainment and customers are encouraged to dress up as pimps and whores. Sounds like our kind of party, interested?"
"Sure, why not?" I replied. Angel and I loved to play dress up and go to fun places. We needed a break from our usual S&M club. "Which one do you want to be, the pimp or the whore?" I asked jokingly.
I checked the place out on the internet and the reviews looked good. High marks on food and good-looking dancers and it was practically around the corner.
We started working on our costumes the morning of the party and by 2pm, had them all figured out. Half the fun in doing these events was the dress up part. Stepping out of our usual appearances and assuming different roles was cool. Kind of like Halloween anytime we wanted it.
Angle looked sluttishly adorable in her black and red bustier top with a black mini skirt, fishnet hose, high heeled black suede boots, scarlet opera-length gloves, red collar choker , heavy makeup and trashy, platinum blonde wig.
I matched her red and black color scheme with my black slacks and boots, scarlet satin shirt unbutton to my chest with heavy gold chain, leather vest, black cape and black felt pimp hat complete with red band, gold studs and peacock feather plume. We take our dress up, seriously.
I teasingly ask her "What do you think is a fair price for your services, if we are approached this evening?"
"Five grand." Angel replied after careful consideration.
"Any restrictions?" I added jokingly.
"No pain, anal, bareback or gangbangs." She quipped.
"Do you do women?" I further inquired.
"Sure, why not? If they have the money."she replied.
We arrived at the club at 9pm. The host greeted us and said "Awesome costumes!"
"Costumes," I replied, "Were we suppose to wear costumes?"
He smiled at the joke and showed us to our table which was to the right of the main state. It had a good view. Several people came up to us and complimented us on our costumes. The girls who were dancing seem exceptionally beautiful and seemed quite adapt at pole dancing. Angel was thrilled with their acrobatic displays and flexibility.
I ordered the sirloin and she had the scallops. They were delicious. After a few drinks I need to pee and headed for the men's room.
While I was using the urinal, a rather distinguished gentleman approached me and said. "I couldn't help but notice that gorgeous woman you were sitting with. Is she available?"
I smiled to myself realizing that this guy really believed I was her pimp and she was a working girl. I decided to play along a little. "I'm afraid you couldn't afford her sir, she is very, very special!".
"Try me." he said.
"Well, her going price is $5000 for a couple of hours and there is no anal, pain or gangbangs allowed." I explained, knowing this would end the discussion.
"It's a deal." He said.
I was stunned. I never expected him to accept the offer. Now I had a real dilemma on my hands. "Let me discuss this with my lady, this is her night off and she may not be in the mood." I quickly replied.
I went back to the table and told Angel what had happened. She was shocked and amused. "Maybe we should play this game out?" She said. "It might be fun to see what it is like being a real hooker, besides, the two hours I spend with him, could pay for our cruise to Hawaii!"
I was shocked at her response, my sweet angel, seriously considering "pulling a trick?" She must be playing with me. "OK, I'll tell him it's a deal." Calling her bluff. She just smiled. I looked at her quizzically, "Are you serious? You aren't really going through with this, are you?"
"Oh come on. Where is your spirit of adventure? Certainly after all your talk about being turned on by cuckolding and watching me get fucked by other men, you're not going to wimp out now?"
"B...b...but that was just fantasy. It was just talk. I don't really want anybody else to have you!" I stammered.
"Remember when you told me that I could date before we got married to be sure I wanted you? Was that just talk or did you really mean it?"
"Ahhh, yeah," I replied. "But I didn't think you would really do it. Besides this is not dating, this is fucking for money!"
"Yes, and a lot of money, come on honey, two hours, let's do it, it will be fun!" She said knowing I couldn't refuse her anything.
"Fun for who?" I answered. "OK, but I drive you to the motel and wait outside. Two hours. I can't believe you want to do this. I really feel like a pimp now!"
I walked back to the table where the gentleman was sitting. "You've got a deal," I said. "But there are a few rules. Money up front, cash and I drive her to the Motel. If you hurt her or try anything, you're dead meat!"
He smiled and said, "I assure you, she will be perfectly safe. After all, it's not for me, it's for my grandson. He's eighteen and a virgin. I have been looking for just the right woman to show him the ropes, a professional, you know, but someone who has a good face and attitude. I have been observing you and her all evening. She seems so sweet, not like your regular hookers. I think she will be perfect!"
Somehow knowing that her trick was a young virgin, made this whole nightmare seem better. I had to admit that having Angel for his first lover would indeed be to his advantage. What the hell. Hawaii here we cum!
I sat in the car in the motel parking lot for what seemed like hours, contemplating the events of the evening leading up to this moment.
What started as a joke in the men's room at the club had turned into the reality of my fiancée, Angel accepting the $5000 for going to a motel with the gentleman and his eighteen year old virgin grandson for two hours of fun and games.
I couldn't stop the dirty pictures going through my mind. I could visualize my sweet Angel sucking the young boys cock while grandpa was giving words of encouragement or possibly participating. If he got any from Angel, I would have to charge extra. Oh god! I was even starting to think like a pimp.
What the hell was taking so long! They have been in there for...oh, it's only been an hour and a half. It seems like so much longer. I felt like a complete fool waiting in the parking lot of the motel while my fiancé was getting fucked in Room 24! Being a pimp, sucks.
Finally Angel emerged from the room and walked wobbly to the car. She got in and we drove home silence. I had a hundred questions to ask, but she did not seem in a talkative mood so I left well enough alone.
Went we got home, she went into the bathroom and took a long hot shower. She then crawled into bed with me and cuddled up. I held her in my arms, a loss for words. Better just to sleep on it tonight.
The next morning she seemed quite cheerful. We had coffee and breakfast, making small talk. Finally, I couldn't stand it any longer. "Well, are you going to tell me about it?" I asked.
"Actually, it was quite sweet." She replied. "He was shy and nervous but I soon made him relax. He was very handsome and very well equipped. I was surprised he had not girls standing in line, willing to give him anything he wanted. I guess his shyness prevented him from losing his virginity sooner."
"What about grandpa?" I inquired. "Did he participate or just watch?"
"Oh he left after a few minutes." She answered.
He said "A man should have some privacy on such an occasion."
She continued. "He was a real gentleman."
He told his grandson that he "It looks like your in good hands I'll be back in a couple of hours."
"So," I continued. "I'll bet he enjoyed himself, how was it for you?"
"Interesting." she explained. "Kind of like being a dance instructor but much more intimate. I enjoyed showing him the many ways a man can please a woman. He caught on real quick. I introduced him to oral, digital and penile sex and I taught him the many various positions and the advantages of each one. I explained the importance of using words to enhance sex and the rules of post-coital etiquette."
"Did you give him a certificate of achievement upon graduation?" I sarcastically injected.
"Hey, are you jealous?" She questioned.
"Yeah, I guess I am." I answered. "I don't feel threatened by a young virgin, but I don't like the idea of someone else being intimate with my girl!"
"I see." Angel said. "Maybe it's a good time to quit the business. Come here baby, there's no substitute for love or experience."