Ithaca Pt. 02 - Preparing for Camping

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Preparation for the camping trip. Humiliation, Crossdressing.
4.5k words
4.61
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Part 2 of the 3 part series

Updated 06/10/2023
Created 02/06/2021
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This chapter will get into a few fetishes. Check the tags, some may not be for you. The camping trip chapter is almost ready and will more will follow if I get some constructive feedback and people want more.

Now I had another problem that terrified me more than meeting the family of my new gay daddy. I had been crossdressing since I was young. I had started going out in public in college and all through my 20s. I was in no way confident about it though. When I did go out, I would do it in safe places. My first trip out had been at Halloween in college (followed by almost every Halloween after that). Any time I went out in public, besides on Halloween, had been to a gay or lesbian club. Sure, I had been to a store, or stopping at a rest stop in transit somewhere, but I had never dressed full time for a long weekend.

John quickly figured out that I had bitten off more than I could chew. As we continued to talk, I admitted that I didn't know if I could do it. I told him I really wanted to and the thought of spending the weekend with him was wonderful, but I was terrified and did not know how I could carry it off. In his calm patient way, he helped me think it through. With every excuse and objection I brought, he gave me a solution or helped me find one.

1. I didn't have enough or the right clothes for a camping trip- He would take me shopping. He had a few friends that could help. They could even help me with a spa/salon day on the day we left.

2. I was too scared to meet his daughters- He assured me they would be fine with meeting me. They had accepted that he was gay several years earlier when he divorced their mother.

3. I didn't have camping gear- He had plenty and would share with me.

4. I was scared of traveling to the campsite cross-dressed- It was only a few hours. We didn't even have to stop.

5. I was scared of being in the campgrounds- He assured me that it would be safe and in any case he and his daughters would be there to protect me, and they all carried guns.

6. I was in a cast and they were planning on hiking- This was a tough one he conceded. He promised to include some easy "walks" so I could join and would check out any that might be too tough for my walking cast. My ankle was really killing me. I had overdone it in the hot tub

After hours online chatting with him, he got me to say yes. He did this by getting me excited as we had cybersex and fantasizing about having sex in his tent. When I begged to cum, he would only allow me to cum if I agreed to go on the trip with him. I was desperate and agreed without thinking. I then came moaning in my hotel room to the thought of being in his tent raking my nails down his back as he fucked me, and trying to be quiet so the other campers could not hear me.

We chatted every evening after work and I flew home on Friday. We chatted late Friday night and most of the weekend. John kept working on my concerns and generally getting me excited about going camping with him. I did have to spend several hours on Saturday at the emergency room. My ankle was killing me and went to get it checked. The decision was to put me back into a hard cast. I texted john and told him and his response was sincere about my pain and predicament but that I should also get a cute pink cast. I was not thrilled with that idea because I spend most of my time dressed as a boy. On the other hand, I could also hide the cast under slacks for work and a cast boot. I had two. One was like a sandal the other like a blue boot. When it came time and the cast tech asked me what color cast, I wanted, I meekly responded "Hot pink". She was a bit surprised but said OK and pulled out the pink fiberglass tape. I left the ER in a hot pink short leg walking cast.

The next week I was working in a different city. It was uneventful. I kept the blue boot on, and no one saw the hot pink cast. They just realized I was in a cast which brings its own questions. Thursday, I left work and went to the airport and flew to Syracuse. John picked me up at the airport. He was so nice, but it made me so nervous to have the older gentlemen meet me and kiss me at the gate. I was sure everyone was looking at the little gay boy kissing the older man. He was unconcerned.

We got my luggage in the car and headed towards his house. I had brought a lot, my makeup, some clothes, women's underwear as well as my boy clothes that I had been wearing all week to work. As soon as we were on the road, he took my hand to hold. I was nervous but he was doing everything to make me feel comfortable. We talked the whole way. Well, he let me talk the whole way. He would ask questions and I would ramble on. I soon had his hand in both of mine and I was caressing and tracing my fingertips on hand and arm.

It was very late by the time we got in, but I was very horny. As john was getting undressed and had just removed his pants, I walked up to him and nuzzled in and started trying to kiss him.

He gently told me "I think it's a little late to get started tonight. You have a few appointments in the morning and tomorrow is going to be a long day for you.

I looked up at him with a pout and reached down to grab his cock gently with my hands and said "I have missed you so much and I want you. Please just let me suck your cock. I want to please you."

He smiled a big smile and said, "Ok you can suck my cock but then we are going to sleep."

"Please direct me. Please tell me how to please you," I said pleadingly as I lowered his underwear to the floor and got on my knees.

He started directing me to please him. I licked up his shaft and gently massaged his balls. Every few seconds he would give me an order to do something different. He obviously knew what he liked. It wasn't long and he had me on the bed with my head back facing him. He was telling me how to suck him as he stood above me fucking my mouth. I could tell he was getting close as he grabbed my head firmer and his thrusts got more insistent. I kept sucking and licking as hard as I could, and he came grunting into my mouth. He held my head firm as cum spilled into my mouth. I suddenly realized that in my lust I had forgotten a condom. I had never tasted another man's cum before and I was suddenly terrified of unsafe sex. What if he had HIV or something else? I also didn't want to be rude with my lover. I waited for him to let go planning to run to the bathroom and spit it out. John didn't let go though. He held my head.

Looking down at me he said, "I want you to swallow my cum." I was scared and he could see it. "Go on. It's safe. I test for aids regularly and I tested this week as will you tomorrow. I want you submit to me right now and swallow. I am not letting go until you do."

My mouth was full of his cock and his cum. I could probably spit it out around his cock, but it would run down my face and up my nose because of the way I was laying on bed. Truth be told, I wanted to swallow it. I wanted to submit to this man and swallow. With John holding my head firmly and staring down at me, I submitted. Looking straight up at him I swallowed and watched a smile spread across his face. I started swirling my tongue around his cock to get more and clean him up. He pulled out, leaned over, and kissed me.

"Thank you." He spoke. "Now let's get some sleep."

John woke me up at 7 the next morning. I am not an early riser. He apparently was. He was showered dressed and holding coffee for me. After kissing me gently I got up and padded into the shower. I had shaved all of my body hair off earlier in the week. I showered quickly and got to work on my makeup. This takes me a long time. I am a perfectionist and while I had done several makeovers at places like MAC, I did not think I was that good at it. By the time I was finished and dressed it was almost 8:30.

John explained as we pulled away that the first appointment was for a doctor to get an STD test and get checked out. We had talked about this and I knew that John knew the Doctor. We pulled up at an office building and I nervously followed him into the office. I was incredibly nervous. The waiting room was empty. John talked to the receptionist and told her we were there for my appointment. We got to go straight back. Once in the room, a nurse took information from me. It was a rough experience for me having to give my real name and information while I was obviously dressed as a woman. John held my hand and helped me get through it. He was especially helpful when it came time to explain what I wanted. Apparently, I wanted a full STD panel done to include detection for any anally transmitted diseases. I was so glad that he said all of this. I could never have done it and I was beet red from embarrassment as he said it. The first step was a urine test and the nurse handed me a cup and instructed where the bathroom was to fill it. I returned quickly as the coffee had run through me that morning.

"Ok", the nurse said. "go ahead and take off your skirt and undergarments and hop up on the table. We will get you checked out."

I had not thought this through. I had assumed that it would be a blood or urine test. That was part of it, but it apparently involved a physical exam. I was really nervous and embarrassed as I took off my skirt and panties and I climbed up on the table. The nurse was very professional as she lifted each leg and put them in the stirrups. Each stirrup had a king of soft boot on it that wrapped around each ankle and foot and had Velcro that held the boots closed. The boots were similar to the Camwalker that I had worn before the cast. The effect was that my legs were effectively tied up in the stirrups. I was lying there exposed to the world with my legs locked wide. The smirk on John's face was priceless as he enjoyed my discomfort.

The nurse went about her business gathering stuff and taking a blood sample. In the meantime, my cock grew fully erect, and my shame grew with it. After drawing my blood, the nurse did an examination of my erect cock and balls which required her to use her rubber gloved hands to hold my cock and gently squeeze it and my balls. John had gotten up and stood by my head and taken both of my hands. He was holding them firmly and I realized that I was essentially in bondage with my feet tied in the air and arms held by john. The nurse was continuing her examination oblivious to my arousal and discomfort. After she finished with my genitals, she grabbed a speculum and lubricated it and rubbed a little on my sphincter. She explained that it might be a little cold and uncomfortable, but the doctor needed to look inside since john had essentially admitted that I was at risk of anal STD's.

As she pushed the speculum gently inside me and opened it up, I was getting more embarrassed. My cock was twitching, and I could feel precum coming out. She was seated between my legs looking up inside of me. After a few minutes she said, "Ok the doctor will be with you in a few minutes. Hold tight." She stood up removed her gloves and left the room.

As soon as the door was closed john said, "I think you are enjoying this."

I was. It was embarrassing and humiliating but I was fully erect and enjoying it. It was amplified by the fact that I was in bondage with my legs tied in the air and John holding my hands above my head so I could not move.

There was a knock at the door and the nurse stepped back in, started putting on gloves and said, "unfortunately the doctor is a little delayed. It will probably be 15 minutes before he can see you. I will remove the speculum and let your legs down while you wait."

John looked at me and quickly said, "No that's alright. You are OK aren't you honey? You can just wait like this?"

He was squeezing my hands firmly as he said this to both of us and I got his point. He wanted me to stay like this in bondage.

"Yes, I'm fine. You can just leave me like this."

The nurse seemed a little perplexed but said, "Ok then. The doctor will be with you when he can."

She removed the one glove she had on and left the room. John laid my right wrist across my left and held them both down against the table above my head trapping them and reached down with his other hand and grabbed my still erect cock and started stroking it.

"15 minutes to torture you in bondage." He said with a devilish smile.

I was terrified but turned on and whimpered as he stroked my cock.

"You love being in bondage in front of people, don't you?"

I did. This was the most erotic thing I had ever done, and I wanted more. I told John but he already knew how much this was turning me on. He stopped stroking me after a few minutes and unzipped his pants and pulled his cock out. His crotch was next to my head and I turned my head, and he pushed his cock into my mouth.

"Suck my cock slave. Do your duty while you are tied up in this doctors' office. Show your daddy how much you want him."

I was terrified that someone was going to come in the door and see me in this vulnerable position with my legs up in the air and John's cock in my mouth, but I was not stopping. I was sucking on his cock as well as I could with my limited mobility and with no hands. John meanwhile reached back down and was stroking my cock. Both of us were getting close to an orgasm. John came first and he pushed his cock deeply into my mouth almost gagging me as he came in my mouth. I continued sucking hungrily as I approached my orgasm. He stopped as I was on the edge.

"No. You need to enjoy the rest of your exam."

I was devastated. I was so close to cumming. I wanted it so bad, and I was begging him to let me cum. He was enjoying denying me though and refused. He pulled his cock out of my mouth wiping his last drip of cum on my lips.

"Don't lick that off. Leave it. It makes a lovely lip gloss for the doctor." He said as he tucked his softening cock back into his pants and zipped them up.

This was further humiliation, but it could not get much worse. I left the cum there as John continued to tease me. He would stroke me or use his thumb to tease my precum around the head of my cock or rub one finger up and down just under the head. It was maddening. He was keeping me very aroused as we waited for the doctor. When the doctor did knock on the door and come in, John had just enough time to take his hand off my cock and return it to holding my hands just above my head.

"My apologies for the wait. How are you doing John? Good to see you again. Hope all is well." He said like a doctor who was in a hurry. "Alright let's get you checked out. Thanks for waiting."

I don't think I had much choice. I was essentially tied up in here. He and John chatted as the doctor repeated what the nurse had done. After putting on gloves he looked over my genitals, holding my erect and now dripping cock and manipulated my balls as he felt them and looked them over. My cock was oozing precum from all of John's teasing and this was not helping. It did not last long, and I found it almost funny that the doctor was ignoring the fact that I was fully erect and aroused by all of this. I could feel the heat and flush of my embarrassment as he moved to my ass and began looking inside of me. He felt around inside of me probing and looking and then inserted something inside me to look a little deeper. I must admit that it ended too quickly. I wanted so much more as he stood up, removed the speculum, wiped off some of the KY jelly.

"I don't see anything wrong. You look clean inside and out. We will have to wait on the blood and urine tests but barring a poor result there, you appear to clean and healthy."

I had assumed this was the case, but it was still nice to hear. The doctor apologized again for the delay and after a few more comments to John, left the room for me to get dressed. John let my feet out of the stirrups, and I got dressed, which was a problem with tucking my erection under the panties and skirt. It had not subsided as we opened the door and left, saying goodbye to the nurse and receptionist.

Back in the car, we headed for my next appointment at a spa salon. I was silent, still recovering from the ordeal. The spa was owned by a friend of Johns, Felix. We walked in the door and Felix, Jana and Alexa greeted us. Jana and Alexa were both manicurist and stylist and were going to do most of the work today. Felix and John chatted like old friends. I got the sneaking suspicion that at one point in their lives they may have been more than friends. They had organized a lot of things for me this morning. John told me not to worry though. Felix was going to prepare me for a camping trip, not a drag show.

While Felix and John got a coffee, Alexa and Jana took me back to a manicurist table. They each went to work on one hand and within 30 to 40 minutes my fingernails were done. I was surprised when they moved me over and began working on my toes. I got a fabulous pedicure. I did not realize that you put gel nails on toes, but apparently it is a thing. The end result was nails on my toes and fingers that were way too long in my opinion. Don't get me wrong. I think manicured nails on women are very cute and even sexy. I was just worried about peoples stares and reactions to nails this long. I was already embarrassed by their length and camping with nails this long seemed impossible. In my experience camping requires lifting and work and I thought that was going to be a challenge with nails that were almost 2 inches long on my fingers. I had also never had long toenails. I was not sure how this was going to work with hiking boots. I had worn sandals into the salon, and the toenails looked way too long for me. They were at least ½ inch off the tips of my toes.

When Felix walked back and saw me starting at them, he squealed, "aren't those adorable? John failed to mention he has a fingernail and toenail fetish, didn't he?"

Yes, he had indeed failed to mention that. John had left to run a few errands while I finished up. I felt like I was awkwardly walking up to the next chair for my makeover. My pink tipped French manicured long toenails matched my fingers and my cast, but I was very self-conscious about the length. The next hour entailed waxing and plucking of eyebrows and makeup and styling my wig. Luckily, the last part was easy. The lace front wig I had bought was expensive but worth it. It looked like real hair and was not so long that I had to constantly get it out of my face. Brushing it out in the morning was most of the care.

I was sipping a cup of coffee when John walked back in. He walked in and came over and kissed me and said, "Don't you look adorable and Oh I love your toes."

After our goodbyes we got into the car with Felix and went off shopping. I really did not have the clothes for camping as a girl. The first stop was an outdoor store. I felt ridiculous as we talked to the 20 something salesboy about what sandals would work best for very light hiking. He was amused. One leg in a pink cast. ½ Inch long pink tipped French manicured toenails. It was obvious I would not be doing any real hiking. In the end he found some thick sandals. John led me to a chair and after sitting pulled my sandal off and held my toes in his hand and looked up at me. I was very self-conscious as he stared up into my eyes and massaged my toes and felt my toenails. I kept my eyes focused on him terrified that everyone in the store was staring at this man playing with my feet. He finally stopped and put one sandal on my uncasted foot. He told me to walk around and see if it would work. I wanted out of the store as quickly as possible. I was sure everyone was staring at my crazy nails and everyone knew I was crossdressed. I took a few steps to the mirror and could walk outdoors with these and not let my toenails scrape the ground.

Wearing the sandal and carrying the box we headed off to buy clothes. Felix was a doll helping me find cute things. In the end we had several pairs of shorts, a few outdoorsy skirts, a few blouses, and a cute fleece in case it got too cold. The whole time I felt like half the store was staring at me. John and Felix kept me distracted but I was unbelievably self-conscious, embarrassed, and aroused. I could not explain it. I was embarrassed at the attention that the cast and the nails drew, but I was aroused also. It was very confusing, and I would think on this a lot after we left the store.

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