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Somehow, I ended up at a birthday celebration with my cousin, Susan, who had actually been invited. Her “boyfriend” couldn’t attend, so she asked me to be her companion for the night. It was a casual event but classy. A band played soft jazz and some people danced around while the bulk of the celebrants mingled around the pool area.
There was soft lighting throughout the yard and drinks were flowing. Apparently, they had a formal dinner previous to our arrival, but there was still plenty of food around should anyone want it.
I was at the wet bar, requesting a beer, and entered a conversation with another party goer and the bartender. We eventually inquired about each other’s ages—they were both fifty-three compared to my thirty.
They laughed and said.
“We thought you were only twenty-one…if that!”
“Thank you for the compliment.”
I learned the bartender was actually the host of the party, but he was giving the real bartender a break.
“I think that’s very cool!”
The night went on and so did my drinking. I began to notice, but not soon enough, the thinning of the herd as fewer and fewer people were around. Then the guy who was hosting came up to me and asked.
“How’d you come to be here?”
“I’m attending with my cousin.”
“Do you mean, Susan?”
“She…well…wait. What’s your name?”
“Chris, and yours?”
“Sam. Well, Chris, your cousin left about an hour ago…with another guy.”
“That’s just great!”
Sam reacted with a little concern and asked.
“Where do you live?”
“About a two hour drive from here.”
“Let’s get another round. I don’t think you’re going anywhere tonight.”
We sat down and discussed the matter as people left and the band packed up.
“I respect Susan and enjoyed our conversation at the bar, earlier. If you’d like to stay the night, I’ll arrange a ride home for you tomorrow, free of charge, as opposed to Uber or such.”
“So, what’s next? For instance, where would I sleep?”
Sam pointed and said.
“There’s a clean and comfy guest room with access to the kitchen and the patio. Also, the pool is yours to use, if you wish—just don’t drown.”
“Thank you, Sam.”
Before he turned in, he said.
“Since you won’t be driving, drink all of the beer you want.”
I didn’t know what time it was, but later that night, I woke up outside and very thirsty, most likely due to alcohol dehydration, wearing only my underwear. I didn’t remember taking my clothes off nor could I immediately find them.
That wasn’t unusual for me on nights of drinking, but I was at a stranger’s home, so where the hell were my clothes?
All I had to wear was a Zebra-striped, cropped tee and matching string bikini underwear. It was very early in the morning and I was as thirsty as hell, so I got up and walked inside to the kitchen for some water.
I found the sink in the dimly lit kitchen and then a glass. While drinking my second glass of water, the kitchen lights came on and there stood Sam in his robe and pajamas.
“I’m sorry for making noise and I’m a little embarrassed about running around in my underwear, but I can’t find my pants.”
Sam informed me.
“I found you passed out, outside, with beer spilled all over your pants, so I took them and your shirt off, put them into the washer, and since it’s a nice night, just left you outside. Do you want a beer?”
“Sure, but do you have a spare robe?”
“I just figured you’d be uncomfortable with me only wearing my skimpy undies.”
He laughed and said.
“Dude! I was the one who removed your clothes to begin with.”
He assured me.
“No matter. Nobody is around anyhow, so I don’t care, if you don’t.”
So, we grabbed a couple of beers and went outside.
Sam reminded me.
“Do you remember how I originally thought you were twenty-one? Well, I still think so.”
“Why do you still think so?”
“Because only a younger guy can pull off looking good in your outfit.”
“If you’re talking about my clothes that are in the laundry, they’re nothing special but thanks.”
“No, not that. It’s your matching Zebra-print bikini and cropped tee.”
He went on to say.
“Your outfit looks hot, kind of feminine, and you have a great body to wear it. You still have a twink build.”
I was somewhat apprehensive but asked.
“Why do you think my underwear is an outfit?”
“Chris, no guy wears matching bottom and top underwear, on purpose, and doesn’t want to be seen. It’s put together like a girl would. It’s obvious to even the casual observer, like me, you like to be seen.”
I couldn’t believe my ears…he pegged me!
I confided in him.
“Actually, I do prefer wearing skimpy underwear as much as possible, being an exhibitionist, and enjoying the moment.”
“No big deal! Why don’t you go and grab a couple of more beers?”
I hesitated to stand until Sam said.
“Don’t worry about it. I know you have an erection and it’ll Esat travesti be very obvious in your bikini. I also know you want to be seen.”
“Relax. All is good. You said you’re an exhibitionist, right? Well, I want to see!”
So I got up and, while passing him on my way toward the house, he reached out and pinched my butt cheek.
I returned with the beer and Sam said.
“Since your hard, trapped cock must be uncomfortable, you can remove your bikini if you want to.”
He had a point, so I took them off.
“There you go! I’ll bet that feels better! You’re a real exhibitionist now!”
“Chris, do you want me to join in?”
“What do you mean?”
Without answering, he stripped completely naked!
Sam has a very nice body for a fifty-three-year-old male and his eight inch penis is sweet—mine is only five inches.
“You should remove your tee so I can wash your Zebra underwear set as well.”
As I did, an older guy came outside to collect my underwear and Sam’s robe and pajamas before retreating back inside.
“Who was that?”
“My assistant and butler, Tom.”
So there we were, both buck naked, outside, and drinking beer.
Sam broke the silence by asking.
“Chris, I wouldn’t ask this if you weren’t staring at it, but do you wish to touch my penis?”
I walked up to Sam and reached down to hold his cock. It seemed even larger in my hand and it was very warm. He then held mine in one hand, pulled me nearer, and reached around to spank my ass. I had to admit, that interaction had turned me on and he knew it.
“Chris, do you wish this to follow its natural course?”
“Yes, but I’m a virgin.”
With that, the butler (Tom) appeared with a huge blanket and a picnic basket. ‘Was Tom watching us?’
Tom motioned me away from the blanket and told me.
“I’m going to give you an enema and then clean you up in the outdoor shower stall.”
Sam was having a beer and watching while waiting for me. Finally, Tom finished and retreated into the house, again.
“Ok, Chris, let’s fool around in the pool and see what happens.”
Within seconds, we were making out and grinding. His hands were all over me. That was surreal to me, yet very, very sensual. He continued to tease my ass with his fingers, which held me in anticipation.
We got out of the pool and laid on the blanket where we continued our embrace. Then he got up, forcefully flipped me onto my stomach, and aggressively spread my legs.
He grabbed something from the picnic basket before I felt a cool, creamy sensation on my ass and his fingers entering me. Then, Sam took hold of my hips and I felt the head of his cock pressing against my hole.
“Hold on, Chris. Your world is about to change, just the way you want it to.”
With that, his cock sent shockwaves throughout my body as it penetrated my hole, and I screamed out!
Then he pulled out and, while kissing my neck, asked.
“How are you doing?”
“I need more to make the pain go away! It feels better with your cock inside of me!”
He sent me to the stars by tickling my prostate as he, once again, slowly penetrated and drilled deeper! He started to fuck me, sometimes exiting completely, tapping his cock on my ass, only to thrust back in and hit my prostate again.
Sam fucked me for, at least, twenty minutes before he exploded inside of me. At that point, I knew he wasn’t wearing a condom because I felt his warm cum inside of me and running down my balls.
I was too spent to say anything, so we just laid there as he held me and caressed my ass.
Finally, Sam asked.
“Did you enjoy it?”
Since I’d dreamed of it, I said.
“I figured. Do you want a beer?”
On que, Tom appeared, again, with two beers and motioned me over to the shower stall again. He proceeded to wash me down then told me to bend over for a douche.
Afterward, I grabbed my beer and watched Sam shower until he finished, walked over, sat down, and asked me.
“Are you comfortable and enjoying your time with me?”
“Yes, indeed, but I’m wondering why you didn’t use a condom?”
“Chris, first off, rest easy. I’m clean with medical proof. I’d never put you at risk and I took a leap of faith on your sexual health being clean, also because you told me you’re a virgin. I figured you deserved the real deal, breeding, for your first time.”
“What are you saying?”
“You’ll understand, later.”
“I hope so, but I want to express my many thanks for…everything! By the way, what time is it?”
We were both still naked and the sun was rising.
“I’ll arrange your ride, if you wish, but I wish you’d stick around because I’m having a great time.”
“Well, it is Saturday morning and I have nothing planned so, yes, I’ll stick around with you as I’m really enjoying our time together. What do you have in mind?”
“I’m planning to go on a four hour river cruise today and Kızılay travesti thought you might want to join me.”
“That sounds nice, but I don’t have anything appropriate to wear for such an occasion.”
“It’s a very casual cruise, not formal at all, so what you wore last night will be fine. In fact, Tom has washed and pressed them and they’re in the guest room.”
With that, he went to get dressed. I went to the guest room and found my Zebra-print bikini and cropped tee on the bed. I put on my underwear and walked out to Sam, who was waiting.
“I can’t locate my shirt and pants.”
“Are you feeling ok?”
“Chris, you’re wearing them. I told you, it’s very casual!”
Sam was wearing a polo shirt and pleated shorts, so I thought he was joking.
“You’re joking, right?”
“No, I’m not. I want to show off my date by you wearing your outfit on the cruise. It doesn’t really look like underwear, but rather a flirty sun ensemble. If you want to go, this is all I’m going to allow you to wear.”
He was affording me the opportunity to be an exhibitionist without saying it, yet giving a reasonable excuse to be one without admitting it, aloud.
There were about eight couples on the cruise and the gals were all in sundresses—not one was in a swimsuit or bikini. I had quite a few people look at me.
After the cruise, Sam commented.
“Thank you for joining me, Chris. Would you like to go to a gay bar? We’ll go straight there from the dock and I want you to remain in your underwear.”
“Why not! I’m enjoying myself, but what about the indecency laws?”
Sam reminded me.
“Since your tee and bikini bottom have a matching Zebra-print design, your underwear looks more like an outfit. Besides, you’ve already been in public for over four hours.”
Off we went. Entering the bar wasn’t as intimidating as I’d expected it to be because, as Sam said, “I’d been out in public, boating and riding in a car in only my underwear, for hours”, so it was no big deal.
We proceeded to consume beer and enjoy the establishment. Everyone was friendly and I received more than a few ass pinches. I also received many compliments about my underwear—those guys knew it was underwear! Many said, “You have balls to go around in public like this.”
We wrapped up and started back to Sam’s place, stopping briefly for beer.
“I’d be happy if you’d spend the rest of the weekend with me!”
To my surprise, Sam had directed Tom to go on a shopping trip (for me) while we were out. Sam had him purchase new underwear “outfits”—matching thongs for every bikini and tee combo for versatility and also matching waist sashes as accessories—for me to wear and for him to enjoy.
There were numerous new colors and prints—Zebra, Tiger, Cheetah, Dalmatian, and Giraffe. Except for the black set and the white set, all other solid color sets were neon.
All of the tees and bikini bottoms had been taken to a professional seamstress to be altered to my measurements, and Sam’s special desires.
The tees were cropped and hemmed just above the naval and the sleeves folded over three times then sewn into place.
The bikini bottoms had the addition of detachable strips of matching material for the sides—they were adaptable to the thongs as well.
“Do you like them, Chris?”
“I love it all! You nailed it!”
“There’s another cruise at midnight…if you want to go?”
“Can I wear one of my new outfits?”
“You’d better! I wouldn’t have it any other way.”
“Which outfit do you wish me to wear?”
They were all laid out for him to pick from.
Sam thought out loud.
“Hmm. Midnight cruise, casual, mixed straight and gay couples—neon-purple will work!”
He looked at me and said.
“Wear the matching thong, instead of the bikini, and include the waist sash.”
After I’d changed, I stepped out of the room and his face said it all—he loved it! There I was, wearing a neon-purple, professionally cropped tee with sewn, rolled up sleeves—male but gave a baby tee feel—a matching neon-purple thong with the material strips attached on the hips, and a matching neon-purple waist sash.
“Can I add to the outfit?”
“Yes, of course.”
He stood behind me and placed a satin-black choker collar on my neck.
“It’s a signal that you’re taken!”
After Sam got dressed, he emerged wearing a tuxedo!
After we got into the car, Sam confessed.
“I have to confess…I told you a little lie, but you’ll most likely be pleased. This cruise is a gay event and all black tie, except femboys are free to dress up. Tom is coming along in case you have a wardrobe malfunction.”
“How many are dressing up?”
What a fantastic night! All of those formally dressed men, yet I was only dressed in sexy underwear! As the beer flowed, Sam and I were dancing and kissing and we were frisky.
I was in my own little world—oblivious to the people watching us—and didn’t think twice about allowing Alsancak travesti Sam to remove the sash. While we were dancing, he lifted my tee off—I was in heaven! The music was awesome and we couldn’t be separated. He then worked my thong off, which didn’t faze me at all. There I was, wearing only a satin-black choker collar and madly groping Sam while all watched.
Suddenly, chanting began as I unfastened Sam’s pants and instinctively pulled them and his underwear down, which revealed his beautiful manhood. Needless to say, I wrapped my mouth around it and gave him a blowjob to completion right there. Not one drop of his tasty cum leaked from my mouth and I received an ovation from the witnesses as I swallowed.
After I was finished, Sam told me.
“Go clean up. Tom is waiting for you in the bathroom.”
Tom cleaned me up, put my neon-purple tee on me, and said.
“That’s all you can wear, other than the butt plug I’ve been instructed to insert into you.”
That was new, but Sam wanted it. That gave me another erection, but I was only wearing the tee so I’d be comfortable. I returned to the party and cheers rang out. I spent the rest of the night as such and we had a great time!
“Chris, do you want to stop at the bar?”
While handing me my thong, he said.
“You’d better put this on then. They don’t leave much to the imagination, but…the law.”
While there, he asked.
“Are you ok, so far?”
“Just one thing. You didn’t tell me I was to be the ‘entertainment’, as well, at the party.”
“It wasn’t my idea, it just happened. You were the one initiating the show! You were in a moment, so I just let it unfold. I loved it and while you were sucking me, I told Tom to prepare. I figured you’d enjoy it!”
“I’d love to have you stay overnight, again, since it’s still only Saturday night.”
“I accept your wonderful offer.”
We decided to get into the hot tub portion of the pool and make out. Tom came out with refreshments and started some soft jazz playing. Then he lit some floating candles and placed them in the main swim area. That was magical.
Tom came over to me a little later and said.
“Mr. Chris, it’s time to get fresh.”
I knew what he meant and went with him to the outdoor shower stall. That time, he said.
“You just need to grab the rail and bend over for the enema.”
After he finished, he washed me up. Afterward, as Sam and I were rolling around and play fighting on the big blanket, Tom changed the music to AC/DC.
Sam was playing an intruder, bent on raping me, and we were wrestling. The music was driving him and he got me in a headlock.
I did and he flipped me onto my back, lifted my legs, and spread them. Tom appeared and oiled both of us, and then Sam fucked the shit out of me for an hour!
I was spent, so he carried me to my room.
Sunday morning had arrived.
Sam woke me and said.
“We’re to have brunch out on the patio. Tom has drawn a bath for you and will have an outfit laid out as well.”
I got out of the bath and Tom toweled me dry as he told me.
“Sam said you are to wear what is laid out in your room and then join him on the patio for brunch.”
I walked into my room, still naked—I’d been naked for hours by then, so why get dressed—but what the hell, I was Sam’s bitch so his wishes.
Sam kept it simple—a neon-orange top and bikini bottom with the black choker collar. When I walked out onto the patio, Sam was wearing a regular T-shirt and shorts.
“Good morning, Chris.”
Then his guest turned around…my cousin, Susan!
I was shocked!
“Relax, Chris. Susan actually set up our meeting each other and is here to see how we made out.”
I started to speak.
“Chris, you’ve confided in me, for years, about such a fantasy. So, knowing Sam was looking for something similar, I thought I’d help because I love you.”
I was somewhat disoriented from hearing that, yet I acknowledged the truth Susan had spoken about my desires.
“But, Susan, I told you that in confidence!”
“It still is.”
“Susan, I’m confused because Sam knows, now.”
“No. Listen, I know about you being basically a submissive who loves to exhibit himself, and I know you are gay, but you’ve never admitted it to yourself.”
“I knew Sam, who is indeed gay, needed a companion, yet he wasn’t searching for one. A party presented an opportunity to help both of you, should fate allow. Everything that happened between you guys was because of your own actions. I had only been somewhat of a help getting you there. I left the party before you and Sam even met.”
Sam piped up.
“Chris, are you ok?”
I finally sat down and said.
“Yes, I’m good. Thank you, Susan.”
I actually gave her a hug and a kiss, which prompted Sam to ask.
I walked around to him, hugged him, and then we shared a passionate kiss. Sam was so happy—actually, we all were.
Knowing I was embarrassed to tell Sam what I do for a living because he’s a computer guru, Susan went on to tell him.
“Sam, did you know Chris works as a rather talented handyman?”
With that new knowledge, Sam said.
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