Joanns First Time Part 1
- 3 years ago
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Joann's Big Dream Is Taking Shape free porn video
My dream was beginning to take shape. Joe, from the bank, called and wanted us to come down to meet with him to discuss the finances of the vacant motel. I called Chrissy to see if she wanted to join us. She was excited and volunteered her SUV, again. I arranged a meeting for the following Monday so we could drive down on a Sunday. I began to print my calculations and drawings of my proposed “Joann’s Club Paradise” in preparation for our meeting.
That Friday, the four of us sat to discuss the plans. I told them we needed to dress to impress. We had to look professional, yet hot. I suspected that Joe had some hidden personal agenda, given his unexpected interest and cooperation. I was also pleasantly surprised at the money available between the four of us. Both Chrissy and Michelle had decent nest eggs between them. Sis and I had substantial funds, as well as the entire equity in the house since Mom signed it over to us when she moved away. I made up a dozen packets with drawings, prints, financial statements, and an operating plan for the first year.
Saturday, Chrissy and Michelle went to their homes to get their clothes for the trip while Sis and I looked through ours. It reminded me of old times as we took turns trying on various outfits, helping each other hooking our bras, zipping and unzipping dresses, and modeling in front of each other. Sis commented that I came a long way from wearing her panties on the weekend, to having a wardrobe as big as hers and a real set of tits. I gave her a big hug and thanked her for helping me every step of the way.
Chrissy and Michelle brought back Chinese food for dinner. We all ate and then changed to watch some television. Chrissy, Sis, and I put on a nightshirt and panties. We all lay on the floor in front of the television. Michelle came out a few minutes later with a sheer negligee with nothing under it. She stood in front of the television and said, “Let’s have some fun before our long ride tomorrow.” She must have planned this with Chrissy while they were out. She rolled Sis on her back spreading her legs. Then Michelle lay on her stomach on the floor with her face in Sis’s pussy after saying, “Climb on Joann.”
Chrissy urged me on top of Michelle where I pushed my little dick into her ass as she spread her legs a little. Before I knew it, Chrissy was straddling the two of us with her dick pushing against my ass. I could feel the pre-cum on its tip providing some lubrication. Slowly she pushed her dick into my asshole. Her forward pressure pushed me into Michelle’s ass, which in turn, prompted her to lick Sis’s pussy harder. I wish we could have had a video of it. As Chrissy moved in and out in my ass, we all moved with her rhythm. All four of us were moaning.
It was my first sandwich, and I loved it. The excitement in my ass was radiating through my little dick, and apparently, into Michelle’s ass. My tits were pushed into her back and I could feel Chrissy’s tits against my back. Sis had her knees up, so I gripped them with my hands. When Chrissy thrust forward in my ass, I would pull on Sis’s knees. This intensified Michelle’s muff diving. I could see the expression of satisfaction on Sis’s face as she moaned in sync with us.
I was surprised when Chrissy was the first to cum. She cried out a strangely convoluted groan as she gave one long push in my ass. We were all still, as Chrissy finished unloading her cum deep inside me. I could feel her dick pulsing in me, before it calmed down and she pulled it from ass. Then she put her hands on my ass cheeks and started pushing me into Michelle. I was still watching Sis’s face as it started to contort and she began to pant and moan at a higher volume. I think I was as excited as her. When she let out a final moan, I came in Michelle’s ass seconds afterward.
After I pulled out of Michelle, she said, “What about me?” Chrissy rolled her over on her back, spread her legs, and began licking her pussy in earnest. I pushed her teddy up over her head and started sucking her right nipple. Within seconds, Sis started sucking her left nipple. Michelle put her right arm around my head and her left arm around Sis’s head pulling us tight into her two tits. I could feel her body bucking as she squeezed our heads arching her back to push her pussy upward. She was, by far, the loudest when she reached her orgasm. We were all lying on our backs next to each other when we finished off Michelle. Chrissy and I eventually got up and showered before going to bed together.
In the morning, we got up and dressed casually for the twelve-hour trip. Chrissy drove halfway and I drove the other half, stopping for lunch and gas once. We arrived at the hotel around 9:00 pm, eating a late snack before going to bed.
We met Joe, from the bank, for breakfast to talk about the meeting later in the morning with the other lending officers. He looked through one of the packets I made up. He said the reason for the meeting was to plan our presentation, but after looking through my packet he felt we were better prepared than he could possibly plan.
We went to the bank and met with Joe, three other men, and Joe’s boss, before sitting down with Joe and his boss in a conference room. After over an hour of questions, Joe’s boss, Al, stood up and said he was impressed with my presentation before asking, “But, do you think four women are going to be able to handle this? And how did four women get such an idea?”
I stood up, walked over to him, took his hands with my hands and put them on my butt cheeks. Then I put my arms around his shoulders and said loudly enough for everyone in the room to hear, “Only two of us are women, want to guess which ones?” While he turned a little red, he didn’t let up his grip on my ass. I continued, “We’ll give you a chance at that later.” Then I stepped back and said, “This property is perfect for our plan, but is worthless to anyone else. This is a win-win-win. The bank recovers a bad loan, we get the perfect property, and you get a lifetime membership to Joann’s Club Paradise.” I finished by giving him my best sexy wink.
After a minute, Al said, “Well, young lady, you make some very good points. You have made a thorough and persuasive presentation. I’m going to do everything in my power to accept your offer.” Then, he gave me a wink. “You will hear from me in a few weeks. Joseph will finish up the preliminary paperwork with you.”
After Al left, Joseph said, “Wow that went well. We may pull this off. Let me get my folder. We still have a lot of paperwork to fill out and sign.” One of the first items was credit applications for all of us. When I completed mine, Joe looked at it and said, “Your name is Joseph too?”
I smiled and replied, “We have something in common.” I could see the surprise in Joe’s face. I tried to lighten the mood a little by saying, ”I guess we’re going to take the fun out of Al figuring out who’s who the old fashioned way.”
That night at the hotel room, Chrissy asked why I never had my name legally changed to Joann. I didn’t realize that was possible. She explained how I could do it when we got back home since she had done it in the state where we lived.
The next morning we drove back home. The following day I contacted a lawyer who Chrissy worked with through her company to talk about our business venture. He reviewed the copies of the documents we signed for the bank, and then suggested we form a corporation to operate the business and minimize our personal exposure. He agreed to handle everything for the purchase, and as a bonus, would file my name change.
As promised, Al called me personally to tell me the bank conditionally accepted our offer. He asked if I would mind if he flew up to meet me, alone, for dinner to discuss the final agreement. I told him that would be fine and I would even pick him up at the airport. He called back an hour later to tell me he booked a flight for Friday afternoon and a hotel room. I began to suspect it was going to be more than dinner.
I took a long bubble bath with the best fragrance I had, followed by a heavy enema. I put on a black and red lace thong, matching three quarter cup bra, and thigh-high black stockings, before pulling on a tight one-piece black dress that just covered the top of the stockings. I had to raid Sis’s closet for a pair of high heel black shoes since I rarely wear them, but today I was on a mission. I packed an overnight bag and a folder with some information on the motel. Then, I put on a coat, loaded the car, and headed for the airport.
Al texted me, shortly after I parked in a short term lot, to let me know he arrived. I drove around to the terminal and picked him up. When he got in the car, his eyes lit up as he said, “Joann, you are stunning. I’m told there is a great restaurant next to the hotel. Is that okay?”
I replied, “That sounds good. Give me the address.” It was only ten minutes away. He wanted to check in first so he didn’t have to worry about being too late at dinner. I went up to his room with him. While he was freshening up in the bathroom, I sat waiting on a chair with my legs crossed. He couldn’t take his eyes off my legs when he came out. I couldn’t resist asking, with a big smile, “Is my dress too short?”
He was so cute as his face turned a little red and he shyly said, “Oh no, it’s perfect.” I uncrossed my legs, purposely opening them a little extra, trying to give him a little show. The expression on his face confirmed I was successful. As I stood up, he walked over and took my hand. We walked down to the parking lot to my car where I grabbed my folder. Since the restaurant was just on the other side of the parking lot, we walked to it.
I spent the first hour going over details that I wanted to address before we started drinking. After that, we had a light dinner and two bottles of wine. The more we drank, the more Al opened up about his personal life. He was married, had three kids, and his father-in-law was a director of the bank. The motel deal would be quite a feather in his cap since there was little hope of recovering their money from the original loan. Then, we started drinking bourbon and our discussion quickly drifted away from business. He began moving his chair closer to mine. His hand moved to my hand. The waiter came to the table with the check hinting that it was nearing closing time.
Al paid the check and we walked outside. I said, “I hope I’m okay to drive home.”
He quickly responded, “Maybe you should stay at the hotel tonight.”
I countered, “Is that an offer?
He awkwardly answered, “I guess it is.”
I took his hand and walked toward my car as I said, “Let me put my folder in the car and get my night bag.” I opened the car door, put the folder on the seat, and then leaned over to reach my bag.
He put both of his hands on my waist and laughed saying, “I don’t want you to fall over the seat.” As I grabbed the bag, he pulled me back out of the car. I stood up, laughing, and turned face to face with him. He leaned in and kissed me on my lips. I put my arms around him and continued the kiss with several tongue exchanges. His hands were all over my ass. I took his hand, walked toward the hotel, and then up to his room.
Once in the room, I told him I wanted to slip into something more comfortable and that he should do the same. I asked him to unzip the back of my dress. Then I let it drop to the floor. I took a silk teddy from my bag and pulled it over my head letting it drape down on my body. I took my little purse from the bag and put it on the night table. Al was just standing there watching me, so I said, “Well, are you going to get comfortable?” I began unbuttoning his shirt and unbuckling his belt. His pants fell to the floor. I had to help him step out of them. He finally removed his shirt by himself. Together we pulled off his t-shirt. I put my thumbs in his waistband pulling down his shorts. He was packing a good nine-inches of horse cock.
I pushed him up on the bed onto his back. Then I began to lick the pre-cum from the tip of his dick. He started to moan immediately. I wrapped my lips around his big shaft and started descending down on it. I wasn’t sure if it was going to fit in my throat. I knew I was going to have to work it a while to get it wet and slippery if there was any chance of taking it all in. I began moving up and down, pushing harder on each inward thrust in my mouth. My occasional gagging was making me slobber providing some lubrication. I could poke it partway in my throat, but had to immediately withdraw to keep from choking. Al was getting louder with his moans, to the point, I was afraid the nearby rooms would hear him.
I pulled up, keeping the tip in my mouth, as I started to suck. Then, I would lick his slit as he oozed out some pre-cum, followed by more sucking. His dick was becoming rock hard. I grabbed my purse, and pulled out a maximum size condom and a tube of lube. I opened the wrapper, removed the condom, and pulled it over his straining shaft. As I squeezed a generous portion of lubrication on his dick, he said, “That’s cold, baby.”
I replied, “I’ll take care of that.” Climbing on top of him, I pulled my thong down in the back, before lining up the tip of his dick with my hot and hungry hole. While the alcohol helps relax my sphincter, I knew this was a big one that was going to take some care. I pushed back a little, feeling the pressure stretching my anal ring. I pulled up a little, before attempting another small push. I had to start teasing myself by pushing it in and out, less than an inch, more than two dozen times. The combination of spreading the lubrication and loosening my anal ring, made me feel more comfortable.
I was ready to push the tip of his dick through my anal ring this time. As I, again, pushed my ass back, I could feel it stretching to its limit. I could feel the ridge of his tip sliding along the inner ring before it finally passed through. At last, I had the feeling of ecstasy as his shaft began to slither through my sphincter as it began filling my colon. Al let out a loud moan as his dick was disappearing into my ass. I had to put my hand over his mouth. This was preventing me from sitting back so I could fully let the weight of my body push his dick fully up my ass. Fortunately, he quieted down after a few minutes. I leaned my body back to finish my total impalement. This time it was me who was moaning.
When I leaned forward, Al put his hands on my breasts. I can never get over the feeling of having real tits. I raised my hands behind my head. When I leaned forward, his hands were pushing against my breast, and when I leaned back, his dick was pushing as far up my ass as possible. The rocking back and forth was driving us both crazy. Then I started contracting my ass muscles milking his dick. The heat was building in my ass. I knew I was going to explode soon.
Al moved his hands from my tits to my hips as he started to thrust upward. His grip increased. He started panting loudly. Then he declared, “Here it comes, Joann. I’m cumming. I’m cumming. Ohhhhhh shit!” Sometimes, I can feel a man’s dick pulsing in my ass as he cums. His dick felt like a heart beating in my ass. It made my colon spasm. My insides were warm and quivering. Suddenly, I came in the front of my thong.
I stayed in my position on top of him, with my hands in my hair, as the spasms subsided and my ass started to cool. Al put his hands back on my tits. I leaned forward a little to feel him knead them pulling his cock out of my ass a little. Then, I leaned back a little to force it in, again, but it was already softening. I lifted up and his dick slid out completely. I pulled up my thong and lay next to him. He was snoring in less than five minutes.
When I woke up in the morning, he was still asleep. My ass was still a little wet from the lubrication. I put on a pair of stretch pants and a pull-over blouse. I woke him up so he could get dressed and I could take him to the terminal for his flight out. On the way to the airport, I asked him if he thought I should call his bank. He said, “No, I’ll take care of everything.” He was clearly worried about our night together. I knew this was going to work in my favor.
Sure enough, our lawyer called a week later. He said the bank called and wanted to close on the motel by the end of the year. While he was surprised by their urgency, I was not.
December was a great month. We finalized the purchase of the motel with a one-year-interest-only loan, followed by a ten-year note at a low-interest rate. The home equity loan on the house was approved. Our corporation, JCP, LLC, was registered, and our five shareholders began to put up their money. But, the best came on Christmas, when I opened an envelope that Chrissy put under the tree. It was a legal document from our lawyer officially changing my name from Joseph to Joann. Life was good.
Michelle, Chrissy, Sis, and I spent the remainder of the holiday season starting a website, getting internet advertising, designing forms, opening a bank account, establishing an account to take credit cards, and a host of other activities to prepare for a tentative May opening of Joann’s Club Paradise. Michelle and I were going to move down to the motel in January so we could hire contractors and supervise the start of the renovations. Chrissy and Sis were going to continue to work a few more months to keep up their income. I was going to continue my job by programming from the motel. It was going to be a busy five months before opening.
On January 3rd, I went to the DMV, got my picture taken and my driver's license name changed to Joann. The next day we packed up my Jeep and Michelle and I headed south to the motel. Joe met us there when we arrived in the evening. He had the gas and electric turned on the day before. Although it was in the South, it was still cold there in January and February. We wouldn’t be able to turn the water on until the next day when the heating system in the entire building was started. However, we forgot that the hot spring was a warm 110 degrees all year long. Michelle and I lounged in it before going to bed in one of the motel rooms we moved our clothes in.
The next day we contacted a restoration contractor to remove the musty smell from the entire complex due to the years of being vacant. We turned on the water and had the cable company turn on the internet and phone system. Joe hired a handyman who helped us with the minor renovations starting with the office behind the check-in desk. I could do my programming job during the day and work on the renovations at night. As we completed the renovations, I took pictures for our website.
I had a contractor turn the large conference room on the second floor into a salon where Michelle and Sis could transform male cross-dressers into passable gurls. It included a room with women’s clothing and wigs for sale or rent during their stay. The dining room was refurbished with new tables, chairs, and a dance floor. A bar was installed in one corner of the dining room which was attached to another bar accessible outside near the pool. The kitchen was set-up to serve meals and snacks from morning to midnight. There was a lounge area next to the check-in desk with a large-screen television and a big fireplace where people could meet and hook-up.
Outside, the pool was to be recoated and a patio built around it with pavers where lounge chairs would be arranged for sunning. Beyond the pool were the two natural hot springs intimately tucked in a corner of the completely fenced in and secure property. We had a pavilion erected near the outside bar and pool for planned activities such as barbeques and adult games.
In the rear of the property, we were having a beach volleyball court, bocce ball, and corn hole (bean bags) area made. There were occasional tables where couples could have some outdoor intimacy. The entire property was surrounded by evergreen bushes and trees to assure constant privacy on the grounds, which included discreet lighting for night activities.
There were twenty-four guest rooms for male cross-dressers wanting to spend time where they would be safe and accepted as a woman during their stay. The only public access into the complex was at the front desk. Men wishing to mix and mingle would have to check-in, providing identification and negative H.I.V. test results, before being admitted for their visit. Depending on the vacancy rate and balance, guest rooms could be available for men on the first floor. The second floor was reserved for cross-dressers only, where they had easy access to the salon.
Michelle and I were working sixteen to eighteen hours, seven days a week. Joe worked at the bank during the day and with us at night and weekends. He often stayed in the room next to ours on Friday and Saturday nights. Chrissy and Sis were updating and monitoring the website from home while working their regular jobs.
One night, after arranging new lounge chairs around the pool that were delivered during the day, I suggested the three of us soak in the hot spring since we were all groaning about our poor muscles. We went back to the rooms to change. I put on a string bikini, a pair of slippers to keep my feet warm to walk to the spring, and a terry cloth robe. Michelle said she would meet me there in a minute. I walked through the dining room, out the patio door, and through the pool area toward the spring. I thought I did a great job with the lighting design. It was just bright enough to see the path and the spring was dimly lit with shadows around the edge.
Since it was still cold at night, I quickly took off my slippers and robe before stepping into the hot spring. It felt so good, as my body was submerged in the warm mineral water. I could feel the bikini top caressing my breasts making my nipples hard. There were several rock ledges along the sides for sitting. I sat on one and leaned back. I could see Michelle and Joe walking down the path toward me.
As Michelle approached the side of the spring, she said, “I had a great idea. We don’t need no stinking bathing suits.” With that, she took off her flip-flops and robe to show me she was completely naked. Then, she helped Joe remove his towel to reveal he was also naked. They both stepped into the water with only big smiles on them.
Michelle waded over to me with Joe in tow. She stood in front of me and wrapped her arms around me, giving me a kiss on my lips, before whispering to me, “You’re the only one not naked.”
I replied in a very low voice, “You know I don’t like being completely naked in front of anyone.”
She exclaimed, “But, it’s dark out here. No one can see anything. Pretty please, Joe won’t mine, will you Joe?”
He answered, “Joann, you’re beautiful. I don’t know why you’re so afraid.” Michelle started untying the string around my neck, as she was kissing my lips. Then, she untied the string behind my back and pulled my top away from me. She handed the top to Joe and started rubbing my tits with her both of her hands.
“Doesn’t that feel better?” I couldn’t dispute her statement. I just leaned my head back and lightly sighed. She moved her hands down to my hips pulling me off the ledge so I was standing face to face with her. Then, she pulled the string bows on either side of my bikini bottom, pulling it from my body. She also handed the bottoms to Joe as she directed him to put them on the edge. She whispered to me, “Joann, I need this tonight.”
She turned around and backed her ass into my crotch, moving it up and down making my little cock hard as a rock. I took her hint and pushed my dick into her ass. As I was tending to her back door, she waved Joe around in front of her. I could feel her legs spreading. Then, suddenly, I felt an intrusion against my cock in her ass. She was taking Joe’s cock in her pussy and it felt like he was rubbing his cock directly on mine.
She pulled Joe’s hands behind her so they were wedged between her back and my tits. My hands were between her tits and Joe’s chest. Her arms were wrapped around Joe’s neck. Both Joe and I were bending our knees up and down pushing our cocks up into Michelle lifting her off her feet in the buoyant water.
The combination of Michelle’s ass clamped on my dick and Joe’s dick rubbing mine inside her was quite stimulating. Michelle, who’s never quiet anyway, was moaning louder than I ever heard her before. At this point, her feet could no longer touch the bottom as she was suspended between us, hanging by our cocks. Joe and I were moving in perfect synchronization.
Michelle just kept moaning, “Oh, don’t stop, don’t stop, don’t stop.” Then she yelled, “Ohhhhhhhh shit!” She surely had an orgasm. Suddenly she started kicking her feet, which were still suspended off the bottom, declaring, “Here comes another one. Ohhh, Ohhhhhh, Ohhhhhh, Ahhhhhhhhh.” Her whole body froze up. I could feel her contractions inside. I was almost ready to come myself.
Again, she started kicking her feet. She leaned her head back on my shoulder as she hugged Joe hard. Then she demanded in desperation, “Fuck my brains out, give me all you got. Don’t hold anything back. Let’s make it three.” She stopped the random kicking and moved both her legs back and forth in unison. Her backward leg movement pushed my dick in her ass, while her forward leg movement pulled on my dick. “All together now.” She was panting heavily now and could barely get out her last request, “Let’s come together.”
Once, again, her legs tensed up straight and she was contracting heavily inside as she gasped out, “Ohhhhhhh fuck.” I could feel Joe’s cock pumping inside her against my little dick. I lost all control and came in her ass like never before. I almost lost my balance and fell back. Michelle went limp like a rag doll between us as she sighed, “I needed that so bad. Thank you, lovers.” I bent my knees lowering her feet to the bottom as I withdrew my dick from her ass, then letting her slip from my arms. She gave Joe a kiss before hopping off of his cock. Then, she turned around, gave me a kiss and said, “I’m ready for bed.” The three of us went back to our rooms wrapped in our towels. Joe went to his room. Michelle and I went to ours and crawled into bed naked. It was the first time I ever slept naked with a woman.
The next day I got dressed, walked around the building and grounds, comparing our progress to my list. I called Chrissy and Sis on the phone with Michelle and Joe announcing that we would be ready to open on May 1st. Chrissy was going to update our website with the opening date. She and Sis were going to drive down the week before. We had four weeks to finish getting ready. We needed to start watching the funds since we still had to stock the kitchen with food, buy a large variety of women’s clothes and undergarments, salon supplies, and a van to transport customers from the airport. We also had to hire people for the kitchen, bar, and room service.
Joe came through for us, again. He got a late model eight-passenger van that the bank repossessed at a great price, with help from Al. He gave me a contact for a women’s boutique that the bank was financing the business. Michelle and I spent an entire day picking out clothes, bathing suits, lingerie, wigs, and intimates. It was their biggest sale ever.
Chrissy put a section on our website for help wanted. We couldn’t believe the response, mostly young men with an interest in the transgendered. We were able to fill the six positions in less than two weeks. Their salary included room, board, and commission based on our bookings. As an added bonus, they could fraternize with the guests if there was a shortage of matching men. Two of the twenty-four guest rooms were converted into bunk rooms, one for the men and one for the women including Chrissy and I. If business went well, I eventually wanted to have a bunkhouse built outside the fence. We could pay for it with the additional revenue from the two rooms it would free up.
Two weeks before our grand opening, Sis called and asked if we looked at our reservation log lately. The first and second week was completely booked. In addition, there were reservations through September already. We collected over $20,000.00 in just deposits. Joann’s Club Paradise was about to become a reality.
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