Introduction: This is the third installment of the Misadventures of Calamity Callahan. Jennifer Callahan is a luscious blond nymphet that stumbles happily into sexual situations. This story takes place after she and her mother's best friend Trish shared a night of passion in Las Vegas. This story takes place before Jen offers herself to John and Steve before her roommate's wedding. Please read the other two stories to get a more complete picture of Jen's character.
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After that night in Las Vegas, I masturbated like a wild woman. My ass fetish was out of control. When I returned home on break, I would go to my room early each evening, and jerk off like crazy. I was now a two hander; a couple of fingers in my snatch with one hand while the other was under me with a finger going in and out of my butt hole. I would dream for hours about the sex message from that little Pilipino girl and the bed I shared with Trish. And Jim, Ohh Jim, jerking off his monster cock, watching us from the closet.
About a month after Vegas, Trish and Jim stopped by, unannounced. They knew I was home on break they had been drinking and were very playful. Trish threw several double entrées my way. Mom and Dad suspected something. They probably guessed it was secret that Trish and I shared about my boyfriend Tom who also made the trip.
I gasped slightly when I first caught Jim's eye.
"Jen, Hun would you mind freshening Jim's drink," Mom asked?
"Huh, ohh sure Mom." I nervously took the drink from Jim's hand. He gave me a knowing alpha male smile. I hope my parents didn't see that or my embarrassment as I turned away from Jim to grab the bourbon. Ohh shit I hope he wasn't admiring my ass.
"You know Bill," Jim said, "I always enjoy Las Vegas. We should plan another trip. The girls love to shop and maybe we can get in a couple of rounds of golf"
"Too busy right now Jim," Dad countered. "Jen has to go back to college and I have several cases hanging over me right now. Maybe after the first of the year."
"Sure Bill," Jim said, "whenever you guys are available let me know?"
"Well, we have to run," Trish announced. "Ohh and I almost forgot why we stopped by. Jen, sweetie, I left a package for you in the car. We need to give you that bracelet you bought in Vegas. It must have become mixed in with our bags. Would you mind running out to the car with us and grabbing it?"
"Sure, just give me a minute to get some shoes. I will meet you outside." I had not bought a bracelet in Las Vegas. Jim and Trish wanted to talk to me away from my parents. I felt a rush thinking of what they were planning next. By now, Trish must have told Jim that I knew he was in the closet watching us and I that I got off on him looking at my naked ass.
They were standing in front of Jim's black Jag when I caught up with them. Trish gently placed her hand on my shoulder "Hun , I know how awkward this must seem for you as it is for us. Your parents have known us for 30 years and never suspected we were swingers. This is something we have respectfully kept from them. Your choices that night were entirely yours and I don't want you to feel any pressure now."
She then handed me a business card, and said, "We have a group. We are always looking for new members. You might be interested in seeing what we do. We are having a costume get together for Halloween. Part of the fun is the anonymity. If you decide to come, I will send you something to wear, book your flights and arrange for a hotel room. Obviously, I would prefer we keep this to ourselves."
I fingered the card while she continued, "First timers come as the wait staff. In that way you can walk around, serve some drinks and enjoy the show. You will get paid very well. You can always use the extra cash for school."
She then reached in her purse and produced a little jewel box. It contained a gorgeous diamond tennis bracelet. Jim and I wanted you to have this." Jim had stood a respectful distance away during the conversation. Trish hugged me and gave me a soft sensual kiss on the cheek.
Jim approached and I thought of Trish and I together on our knees worshipping his cock. He bent down and wrapped one beefy arm around my waist practically lifting me off the ground. He kissed me on the neck. He didn't say a word. Just his alpha smile.
When I was back at school, I couldn't figure out the logistics of a coed going into town to purchase a Big Jim Dildo, so I had to content with my fingers. I called Trish around mid October and started asking questions. She ways coy, but I had enough information to know that I would be attending my first orgy. I was free to watch or participate in any way I wanted. She assured me that I would not be forced into anything that I did not want to do.
"It is important that you try the costume on before you get there," Trish advised. "Well, Jen what is it going to be?"
"Just one more question, You and Jim, how do feel about being with other people? I mean jealously. That night, you would not have minded him taking me?"
"Jen, please don't you feel any guilt. Jim and I are completely open. As you can imagine, he is absolutely wonderful sexually. I would love to share him with you. We have no jealousy. If you want to understand our world, you have to understand that freedom. Please come and enjoy the experience."
Next day, a naughty girl little bow peep costume arrived in the express mail. Inside the note read " Try everything on. You will have to come home a day early for your final fitting and to pick up your staff. Everything else is included."
I took inventory. There were a pair of white pumps with pretty powder blue bows. The heels were at least 5 inches. How would I serve drinks in these without falling over? There were white lace gloves with the fingers cut out with bows. Next were wonderful silky white stockings with delicate matching little blue bows attached at the thigh. The bows clipped into a lacy garter belt attachment . No panties. Hmm.
The white push up bra was equally beautiful. My 36D's cradled comfortably in the silky material. It felt terrific just trying it on. I looked in the mirror at my boobies. I held them up and started fondling, kissing and licking them in the bra. "Jim would you like to put your dick between by tits? Trish would it be ok if your husband put his big fat delicious dick between my tits?" I scooped my tits out and sucked on each nipple while watching myself in the mirror. Oh gawd I hope my roommate is still in the library.
The workmanship on the dress was obvious. Thin lacy material billowed delicately under the skirt. It was high enough so that if I bent slightly my nether regions would be available. I took some time to admire my ass in the mirror. If I was to be exposed like this I wanted the view to be perfect. I decided to be completely shaved, lotioned and slightly perfumed for my debut. A big blue bow was attached to the back of the dress and the front was trimmed in the same powder blue suggesting a layered apron. A blond wig, a beaded white mask and a big white hat with a blue bow finished the ensemble.
I arrived at the designated house for my final fitting. I had changed into my outfit before arriving for a more dramatic entrance. The added height of the heels, and the mask gave me a feeling of power and authority. I walked slowly to the house already loosing myself to the character.
The door of the mansion flew open revealing a swirl of activity like a dress rehearsal for a Broadway play. There was catered food and several seamstresses working on girls in various stages of dress and undress. A flaming gay in a white tuxedo and a white hat not that much different than mine, ushered me to a makeshift fitting room lined with mirrors. The tailor, bald, fat, extremely short, ugly and equally flaming gave me the once over and nodded.....
"Good choice...good choice..." He stood on a carpeted box to adjust my hat and play with the wig. " Wonderful you will make a fine addition to our little cast of characters." He then hopped off the box. One other thing dear would you mind turning around. His face was now ass high and flipped the back of my dress up to check out my ass and pussy. He grabbed my butt with both hands and parted my back end with his little thumbs. " Ohhh wonderful" he said, and actually heard him inhale. The little perv sniffed my ass.
At that point I was ushered into another room where I was given a gold staff and last minute instructions. I would be staying at the best hotel in Hollywood. I was to be picked up 6:00pm and dropped off at 3:00am the next morning. You will be picked up again at 9:00am for your flight back east. The room and any meals or incidentals have been taken care of. I was to be given a base salary of $1,000 cash. I was free to earn any additional tips based on my skills and performance. My combined earnings for the night were to be given to me at 3:00am.
I was then greeted and spot checked by two middle aged women that appeared to be the "producer" and the "director" of the event. They asked me several questions including if I understood what was going to happen here and if I was ready. It was all so professional and organized that I could only imagine how the next night would be.
I was given final node of approval and ushered out. As I left I noticed the detail of the decoration. In the center of the reception hall a large very well detailed fountain in the shape of a giant phallus was being assembled. It had be 15 feet in height with an extremely intricate vein structure. Two workman were screwing the cap or dick head on the shaft. They paused to look at me looking at them. The filthier of the two winked at me. Water would flow from the top of the fountain and be caught in a bowl at the bottom and then recalculated. It was a very impressive center piece.
Two curving staircases up to the second floor would provide the visual framing for the big dick when the guests arrived. Large pillows and staging platforms were being organized in circles around the edges of the room. An open space was kept in the center would be for dancing. Lights and DJ equipment was being set up at the top of the stairs on the second floor landing. There appeared to either a fog machine on the second floor as well.
I went back to the hotel and ordered up some gang bang porn and, of course, masturbated. I then took a long shower, grabbed room service and got some rest. The limo arrived on time and I was taken to the back of the mansion through the servants' entrance.
I changed into my costume and was given a large silver serving tray with condoms, lubricants and various sexual toys. The door would fling open and the sound of sexual excitement and pounding music would explode into kitchen. People were running in and out taking drink; food and whatever else orders. It was organized like a five star restaurant.
One of the cast members, sweet face, thin, dressed like school girl, plaid skirt, argyle socks, starched white blouse, stopped me in the kitchen. "Hey, hey little bow peep...little bow peep.. watch out for that fucking little gnome. I was little bow peep last year. He tried to lock me into a dog cage with him."
She spun around quickly lifted her tray up high in the air and kicked open the kitchen door. I noticed a little candy stripped plug in her butt with a ring attached looking much like a baby's pacifier....humm...interesting people, with shared interests.
I took a deep breath, turned my back to open the door, and pushed through. Even with seeing the prep, I was overwhelmed. At least 150 to 200 very beautiful people: fucking, sucking, jerking off, jerking each other off; laughing, eating; drinking; all in elaborate expenses looking costumes. Girls with incredible bodies glistening and gyrating in the stage light. The platforms were built into large elaborate looking stages some were enormous beds others very detailed looking dungeons or makeshift jail cells still others were designed as showers and bath tubs.
