Joanns First Time Part 1
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Joann's Club Paradise free porn video
Sis rented Mom’s old bedroom to two of the gurls on my soccer team. They would also look after the house so she and Chrissy could come down and join us as we spent the last week preparing for the grand opening of “Joann’s Club Paradise”. When they arrived, Sis and Michelle started on setting up the salon. They couldn’t believe how good the old motel looked.
Chrissy set-up the booking and charge system while I worked with the newly hired cooks and bartenders stocking the kitchen and bar. Joe worked with the handyman finishing up the outside grounds and pavilion. We all worked until late at night, leaving no time for anything else.
Although I had a landscaper make the front of the motel look beautiful and the parking lots coated and relined, I only had one sign that displayed “JCP” on the front of the building. There was another sign at the parking lot entrance and one where the road met the main highway. I didn’t want to attract attention, discretion was paramount. Our customer base was strictly through our website where we advertised our discretion using the “JCP” identification.
Anyone traveling by road would surely have GPS. A large percentage of those booked, so far, were flying in utilizing our shuttle service. However, once in the complex, the “Joann’s Club Paradise” name was everywhere, giving it a resort look and feel.
On the day before our opening, we had a practice run to make sure we were ready. We gathered in the dining room in the evening and opened a few bottles of champagne to celebrate. I thanked everybody for all of their hard work. I explained that Joann’s was to be a casual atmosphere, but with the customer always first. I told the new employees that Joann’s was a family and I wanted to get to know each one of them. One of the cooks jokingly said, “I can’t wait for that.”
After our celebration, we went to the two guest rooms that were still serving as our bunk rooms. Joe knocked on our door and asked if anyone wanted to relax in the hot spring with him. Chrissy and I said we would go. Sis and Michelle wanted some alone time. I put on my string bikini and a pullover cover. Chrissy also wore a skimpy bikini. We walked out to the hot spring, taking off our covers, before stepping into the warm rich water. Chrissy hugged me tight and gave me a kiss as she said, “Joann, I’m so proud of you. What you’ve done here is incredible.” I hugged her feeling my tits flattening against hers.
“Are we interrupting?” It was Joe and one of the cooks walking up to the side of the spring.
Chrissy replied, “No, not at all. Come join us.”
Joe asked, “I still don’t have a bathing suit. Is it okay if we’re in our birthday suits?”
Still embracing Chrissy, I responded, “Of course it’s okay, Get in here and show me what you gave Michelle last month.” Joe and Kevin, the cook, waded in toward us. As Joe approached, I reached out and grabbed his dick with my one hand, as I commented, “Not bad.” He chuckled as I slowly started to jerk him off.
Chrissy followed my lead and took Kevin’s dick in her hand. We continued our embrace while jerking them off with our free hands. Joe had a hand on both my ass and Chrissy’s, while Kevin did the same from his side. I kissed Chrissy full on the lips pulling our tits close together, again. Joe started to move around behind me, grasping my waist with both hands, and grinding his boner in the crack of my ass. I broke off my kiss, leaning my head back, as I asked, “Do you have something to cover that?”
Joe answered, “Not with me.”
I shot back, “It’s a good thing I’m always prepared. There are some condoms in the pocket of my cover. Get two, in case Kevin needs one.”
Chrissy said, “Jo, you’re always thinking. You deserve to be the boss.”
Joe waded to the side, got the condoms, and waded back. I looked at him, then said, “I think you’re going to have to put that on above the waterline.” He looked a little embarrassed as he handed one of the packs to Kevin before walking toward one of the ledges sticking out. He climbed up on the ledge, opened the wrapper, and rolled the condom on his cock. Then he stepped back in and waded back over behind me pulling down my bikini bottom. I could feel his dick probing my cheeks for my entrance. At the same time, Kevin moved to the ledge, getting his condom on.
Suddenly, I felt the tip of Joe’s dick penetrating my ass. It had been a while so there was a little pain. It must have shown in my facial expression. Chrissy, squeezed me tight in her arms, kissing me on my lips. The pain passed quickly as his dick passed through my sphincter and into my colon. I let out a little moan sending my lips into a smile that I’m sure Chrissy could feel, since I could feel her lips turn to a smile. I pulled my face back a little from hers.
Then, I could see her frown, as she was obviously feeling some penetration pressure herself. This time, I squeezed her and kissed her to help with the entry. Again, I could feel her lips turn into a smile. As I held Chrissy, I pushed my ass back into Joe’s crotch. His hands were tight on my waist. When he pushed forward, driving his dick deep up my ass, he lifted my feet off the bottom a little. I kept my balance by holding onto Chrissy. When Kevin pushed into Chrissy’s ass, she used me to keep her balance. This was the second time I had sex in the water and I was really liking it.
The combination of the warm water and continued friction in my ass gave me a warm soothing feeling throughout my entire body. Chrissy and I kept exchanging kisses while the guys supplied the energy that seemed to bounce back and forth between us. It had been a long time since I felt this good. At one point, my feet were off the bottom for several thrusts so that I was literally floating. Chrissy and I kept looking into each other's eyes, sharing our expressions of our sexual workout. We occasionally exchanged moans between us as we could hear the grunts of our servants in the background. This was truly a bi-sexual experience for me.
I could feel my ass beginning to spasm, followed by my balls tightening, as I uncontrollably shot my load. I couldn’t and didn’t want to restrain myself as I bellowed out a long satisfying moan. Chrissy’s smile was the icing on the cake as she gave me a little kiss. Then, I heard Joe give out a groan as his dick tensed up in my ass, before feeling it twitch several times, as he squeezed my waist tightly. I lifted my feet up and twisted my legs around Joe’s waist as I absorbed Chrissy’s back and forth motion.
I stayed in that suspended position being stretched and contracted for a few minutes before Kevin declared, “Here I cum.” When he finished, I released my grip on Joe and his now soft dick slid out of my ass. I was now standing on my own two feet, still embracing Chrissy. She had a frustrated look in her eyes. I pulled her to the side of the spring and lifted her buoyant body onto one of the rocks. Her bikini bottom still being down, I put her dick in my mouth.
She grabbed my head with her hands guiding it up and down on her as I worked to bring her to a satisfying climax. She gave a slight gasp before she unloaded four or five hot streams of cum into my mouth. I let her fill my mouth before looking up at her, smiling, and then swallowing. She immediately dropped back into the water, giving me a big hug and a full-tongue kiss. We pulled up each other's bottoms up before stepping out of the water.
Kevin asked what he should do with his condom. I told him there was a trash can near the pool. But, it made me realize that we should have condoms available throughout the complex. Joe said he wasn’t sure where his condom went. I reached back to check my ass. As it often happens, it was still partially in my ass. I smiled as I said, “I still have one of the tightest asses around.” I pulled it out in the bathroom in our room. Chrissy and I changed into nightshirts and panties for bed. Tomorrow was going to be a big day.
The next morning, Joe drove me to the airport in the van. It was a small regional airport that included three daily flights back and forth from the international airport a few hundred miles away. We had three guests coming in on the first flight. I wanted the first person to come in contact with our customers to be a gurl. There was a waiting area for taxis and shuttles at the small arrival area. Since we had “JCP Shuttle” on our doors, we were allowed to wait for our guests.
When I noticed a man walking towards the van, I got out and greeted him, “Hi, I’m Joann from JCP, it’s good to meet you.” Joe came around, took his bags, and put them in the back. I opened the door and handed him a brochure as he sat down. A few minutes later, another man came, followed by a third. I repeated my greeting and seated them with a brochure.
The front of the brochure had a picture of me with a short story about my transformation. I could see the three of them studying me closely. I wanted to give our guests confidence they would receive professional attention to passing as women during their stay by showing them a real, live example. The inside of the brochure had a checklist for their salon visit and information on our rates and options. The back had a sign-up to have their pictures taken with a fish, in case they needed to convince someone they were on a fishing trip, rather than a female makeover.
It was important to make our guests feel comfortable. The brochure provided a diversion for the twenty-minute ride to minimize interaction and any awkwardness they might have as men, being with other men, knowing their reason for being there.
When we arrived at the motel, I walked the three to the counter while Joe took care of their bags. Chrissy waited on the first, Michelle waited on the second, and I waited on the third. After checking them in, they were each given a magnetic card that served as a door key for their room, identification for their meals and drinks, and recording any charges for the salon. We each took our guest for a private tour of the facility, salon, and finally to their room.
It took most of the day to check-in our first twenty-two guests. Ten of them had to be picked up at the airport, while twelve drove in. Michelle and Sis went upstairs to the salon before lunch and started the makeovers. They were busy until dinner time. We knew the first day would be the hardest since we would be filling all of the rooms in one day.
I had one of the cooks put out snacks in the reception area so we could get some interaction between the gurls. I introduced Chrissy and myself to the group. One of the gurls said she didn’t believe we weren’t women. Chrissy, without hesitation, walked over to her, took her hand, and pushed it down her pants. “Well, tell everyone what am I, dear?”
Somewhat embarrassed, the gurl declared, “She’s a man.”
As the group laughed, Chrissy smiled and gave her a big kiss. Then she said, “And maybe a lesbian, too.” It was a great ice breaker. The reception area was buzzing with conversation. Everyone seemed comfortable. I almost hated to announce we were serving dinner in the dining room.
At the same time, a few men came in for the “mingle time” we posted on our website. They had to check-in at the lobby counter, show their identification, and pay for dinner and unlimited bar. In addition, our male staff, not on duty, also came in for dinner to socialize as an added benefit to their employment. All of our female guests that checked in the first day purchased our package deal that included all meals, snacks, and drinks. This worked out well since most socialized at the bar, reception area, and dining room for hours while drinking.
Our first and only activity for the first day was a campfire in the fire pit situated near the outside bar in front of the pavilion. As I walked around, I was pleased to see that the men were beginning to pair off with the gurls. There were two couples in the reception area, one couple at the inside bar, and three couples at the outside bar. I saw one couple wander out back toward the secluded volleyball court. Some of the gurls seemed content to socialize amongst themselves around the campfire. Michelle, Chrissy, Sis, and I stayed at the campfire with them to assure they were enjoying themselves. The gurl that questioned the gender of Chrissy and I earlier said to Michelle, “I’m not sure I should ask, but are you a male or a female?”
Everyone became quiet as they waited to hear Michelle’s answer: “Well, what do you think?”
“I’m not sure what to think anymore. That’s why I asked. All of you look like women.”
Michelle answered, “That’s because we are all women in the eyes of the world and that’s the way it should be. What are you tonight? Did we do a good job and make you a woman?” I thought for sure Michelle was going to do the same as Chrissy did. I was proud of her answer. The gurl acknowledged that she felt like a woman and hugged Chrissy to the delight of the group.
Our cook and bartender, who finished their shift at midnight, came out and joined the group for a few minutes, before each inviting a gurl to join them for some late night fun. As the fire burned down, we all went to our room. It was a long and successful day at Club Paradise.
In the morning, I walked around checking with all of our male employees to see who “serviced” a guest, so far. I wanted to make sure every guest had at least one opportunity at sex during their stay. Then, I greeted our guests as they came into the dining room for breakfast to ask them if we were meeting their expectations. This was an easier day since all of our guests were checked in for at least three days, so there were no check-ins for two more days.
Our first group activity for the day was beach volleyball. Most of the guests showed up. It was a good opportunity for them to function as a woman in a somewhat public setting. It reminded me of my first soccer practice as a cross-dresser. It was clear that most were becoming more comfortable and enjoying their experience. It gave me a tremendous feeling of satisfaction.
Michelle and Sis were busy touching up some of the gurls in the salon. Many went to look at additional clothing to buy and rent. One of them asked if we sold items online. Sis told Chrissy and I. Chrissy immediately started setting up a section on our website for purchasing women’s clothing and lingerie in the office behind the check-in counter while I attended to the counter. One of the gurls, named Carla, came to the counter for some assistance. She said this was her first cross-dressing experience outside her house and she was nervous about moving forward with a man. I thought about it for a few minutes, and then told her we would be glad to help her out. I made an appointment to see her in her room at four fifteen.
Chrissy took over the desk at four o’clock. I went to our room, dug out some of my old toys, and put them in a bag before pulling on a loose dress. Then, I went to Carla’s room and knocked on her door. I could see she was quite nervous, so I told her to relax and sit on the couch. I turned on the television to one of our porn stations and then called the bartender downstairs to bring up a bottle of wine. I poured us both a glass of wine before sitting next to her. I asked her what sexual act she would like to experience. When she hesitated to answer me, I suggested she start with cock sucking first. I turned the channel to one with a woman giving a blow job to a moderately endowed man.
As we watched, I told her about my first experience with Bob, many years ago. I took my dildo out of the bag and handed it to her saying, “Here, hold it while we watch.” Then, I took another dildo out of my bag and began licking it keeping eye contact with her the whole time. “I love sucking cock. I think it’s so hot. Give yours a try.” She raised it to her mouth and mimicked me, licking it like a lollipop. I put my lips around it taking it a few inches into my mouth. She did the same. Then, I said, “Don’t try this at home.” I tilted my head back and pushed my six-inch dildo into my throat leaving only the end of it sticking out of my mouth. After pulling it out, I told her, “That takes a lot of practice. I wouldn’t try it for a while.” I could see the amazement in her eyes.
I poured us both another glass of wine before calling Chrissy at the desk asking her to find Kevin and send him up to room 208. We continued to watch the porn, licking our dildos. A few minutes later, there was a knock on the door. I got up, opened the door, and invited Kevin to come in. He walked in asking, “What’s up, Joann?” I told him I needed him to stand near the television. Carla looked at me, wondering what was going on, also. I walked up to Kevin, untied his sweat pants, and pulled them down to his feet. Then, I pulled his boxers down to his feet, before getting on my knees.
I started licking the tip of his dick, which began to make it hard. I looked over at Carla and said, “If you get the urge, come join me. It is really quite enjoyable.” I began to lick up and down his entire shaft keeping eye contact with Carla and making sure she had a clear view of my activity. Then, Kevin gave her a wave over. She stood up and came next to me. I reached out and took her right hand, holding it on Kevin’s now fully hard dick, as I continued to lick the tip. Kevin urged her down with one of his hands. She was face to face opposite me.
I told her, “Take a little lick.” She stuck out her tongue and touched it on his tip. “Well, what do you think? Not bad, is it?”
She gave me a little nod and a smile. We both started licking up and down on our sides of his dick. I moved around a little, put my mouth over it, and took it completely into my mouth, going partially into my throat. Then I bobbed up and down on it several times, before pulling off. I directed the dick to her mouth instructing her, “Do what comes naturally, but don’t do anything you don’t want to.” She took the cock into her mouth and pushed her head forward. Kevin put his hands on her head, but let her move at her own pace. It didn’t take her long to start bobbing it in and out of her mouth. I asked, “Do you want him to cum in your mouth? You don’t have to if you’re not ready for that yet.”
She pulled his dick out of her mouth answering, “I’m not sure.” I nodded in a “no” motion to Kevin.
She put her mouth back on his dick and started bobbing and sucking. I put my hand under his balls and rubbed them at the same time. After a few more minutes, Kevin said he was almost ready to cum. Carla pulled back, not sure what to do. I leaned forward taking her place. Kevin put his hands on my head forcing his dick into my throat. I still had my one hand on his balls. I could feel them tightening as he held my head down on his dick, before pumping his cum into my throat.
I felt at least four good shots as his cock ejaculated his load from his balls. He suddenly became still and quiet as he continued to hold me in his headlock. As his dick started softening, he finally relaxed his grip. I pulled back freeing his dick so I could breathe and swallow. I could hardly taste his cum, since almost all of it, went directly in my throat, bypassing my mouth.
Carla immediately started apologizing for pulling off. I assured her it was no problem. I pulled up Kevin’s pants and patted him on the ass saying, “You can go now.”
After Kevin left, Carla said, “Thank you for being so understanding and patient, I really did enjoy it. Next time I’m not going to hesitate, I’m going to swallow.” I smiled as I knew she meant it. I gave her a little hug and kiss before leaving.
When I got back to the desk, Chrissy asked me what I was so happy about. I told her I felt like we were really helping people. She said, “I know, but I think we’re going to need more help helping them. We need people for the desk at night, cleaning the rooms, changing the linen, and maybe security. I looked over the receipts and reservations; we can easily afford the extra help. We still have a bunch of requests to work here from our website.”
I replied, “Let’s do it, then.” I enjoyed interviewing job candidates and I wanted to see a few more gurls for the counter, as well as, a few more men for the guests. As I was talking with Chrissy about the details, Carla came by the counter and took my hand thanking me for helping her, slipping me a twenty-dollar bill. Chrissy asked, “What was that all about?” I told her I helped her out a little.
It was dinner time, so I went into the dining room and sat at one of the tables with two gurls. “How are you gurls doing tonight?”
The first gurl answered, “Good, this has been everything I could have expected and more.”
The second gurl said, “That’s because you got laid last night. I haven’t been as lucky.”
I told the second gurl, “We’ll work on that, stay close to me tonight.” The three of us ate dinner and had a drink. I excused myself for a few minutes, telling them I had to check on something. I went to the bar and told the bartender I was probably going to need his services tonight for Barbie, the gurl I was sitting with, after his shift was over. He nodded his acknowledgment. I went back to the table and had another drink with both gurls before inviting Barbie to join me in one of the activities in the pavilion outside. It was a game we called ‘Big Wheel Turning’ where each gurl took a turn spinning a big wheel mounted on the wall. Then, they had to perform the task it stopped on.
The first gurl to spin had to put her hand in her panties and fake an orgasm. The next gurl had to let another gurl rub her tits and act excited. When it was Barbie’s turn, she had to jerk off a nine-inch dildo mounted near the wheel until it squirted out some fake cum. It was controlled by a switch that Michelle turned on behind the podium next to the wheel. Barbie asked me if I was going to take a spin. Everybody urged me on until I couldn’t refuse.
For my spin, I had to deep throat another dildo mounted on a pole. It had marks on it every inch to show how much was in your mouth. Michelle rolled a clear condom on it. There was a spotlight shining on it from above. Each gurl was yelling how many inches they thought I could take. No hands were allowed and it ended as soon as the person backed off. I parted my lips and started taking it in until it reached the back of my mouth. Then, I quietly went: ‘ahhhh,” before moving my head forward forcing it into my throat slowly. The crowd started counting, “6, 7, 8, holy shit, 9, I can’t believe it, 10 fucking inches.”
They were cheering when I buried ten inches in my throat before pulling off of it. Michelle announced on the microphone, “Isn’t she the hottest?”
By this time, I noticed there were three men in the audience. I took Barbie over and introduced them to her. We walked over to the outside bar, ordered drinks, and brought them back to the pavilion continuing to watch and play the big wheel. Finally, one of the men asked Barbie if she wanted to take a walk. She smiled at me and asked me if I’d mind. I told her, “Of course not. Have fun.” When the bartender finished his shift at midnight, Barbie was still not back. I told the bartender he was off the hook.
The next morning at breakfast, Barbie came to my table, kissed me on the cheek, and said, “Joann, thank you so much, you’re the best.” I think I felt as good as she did.
Chrissy, who was sitting next to me, said, “You are the best, Joann. I can’t believe how well this is turning out. Our customers are really coming out of their shells. It makes me want to take the next step, myself.”
I replied, “What do you mean by the next step?”
She answered, “You know, finish my transition and become a complete woman. I’ve been thinking about it for a long time. Don’t you?”
“That’s a big step, Chrissy. I have thought about it many times, too. But, we have so much going on right now and our customers relate to us so well.”
“I’m not going to do anything for a while, but I want to start considering it. I would like to invite our therapist here. You haven’t seen him since last year. What do you think?”
I answered, “I guess it can’t hurt. But we don’t have any rooms available. Where would he stay?”
Chrissy replied, “I’m glad you asked. That leads me to another idea. I think we should buy a few camper trailers. We’re out of room here and we still have acreage left behind the fence. Let’s get Amanda, Michelle, and Joe, and walk out back.”
After breakfast, the five of us walked around the back. It was the first time we really explored the entire property. Joe pointed out the ribbons left by the surveyor indicating the property boundaries. There was a small hill directly behind the motel. From the top of the hill, we could see a large lake that our property borders. At the bottom of the hill to the side of the property was a small stream from the constant water running out of the two hot springs inside our fence. The stream was cool by the time it reached the lake. It was a beautiful property.
Joe said he would call Al, from the bank, to see if there were any repossessed camper trailers. “I don’t know why, but Al really goes out of his way to help us,” said Joe. I just smiled thinking of the night Al and I consummated our business relationship.
Once, again, Joe came through for us. He took us to two camper dealers that had some newer trailers that were repossessed by the bank. We picked out six of them to move to the hill after getting electric, water, and sewerage installed and land cleared by contractors. This gave us more privacy and freed up the last two rooms in the motel. It also enabled us to hire a few more employees giving them more private accommodations, which was part of our salary package.
By July, we were fully staffed, fully booked for the year, and situated in our trailers. Life at Joann’s Club Paradise was finally stabilizing. Al, from the bank, sent me a thank you note for becoming one of the bank’s best customers. We had all of our accounts with him, bought all of our supplies from his customers, and took some of his repossessed vehicles and trailers off his hands. He finished the note saying he would like to personally thank me some time. I would be sure to arrange that.
We spent the remainder of the year developing Joann’s Club Paradise into the premiere resort for cross-dressers and transgender. Chrissy invited our therapist down to stay for a week. Both Chrissy and I would start exploring the final step. More on that later.
Cheryl
- 16.05.2022
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- Category:
- Crossdressing
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