A gay story: Oh What a Night Oh what a night.
Hi, I’m Harry, a 31-year-old married man. My wife Paula and I have a fulfilling sex life, but I’ve always been curious about anal play. However, I haven’t mentioned it to Paula because I don’t want to make her uncomfortable.
One evening, our new neighbor Tony stopped by to invite us to a party on Saturday. As our nearest neighbors, he felt we should join in on the fun. The catch? It’s a gender-bending party where we have to dress up as the opposite sex. Without hesitation, Paula and I agreed to attend.
The next day, we rummaged through our wardrobes to find suitable outfits. Paula sported a pair of chinos and a Hawaiian shirt, while I opted for a strappy top, mini skirt, and white knickers. After adding a fake mustache and doing my makeup, I was amazed at how beautiful I looked. However, the mini skirt was a bit too short, barely covering my knickers, which were too small and barely containing my excitement.
Despite my concerns, we headed over to Tony’s massive house, which we had been given a tour of by the previous owners. With multiple reception rooms, a library, six bedrooms, and a summerhouse, I was in awe.
“Plenty of room for a party then.”
I rang the doorbell and after what seemed like an eternity, Tony answered.
“Harry, pleased you could make it. We thought you weren’t coming. The party is in full swing. Come on in.”
He led us into the hallway then stopped.
“Before we go any further, I have a confession to make.”
“That sounds ominous,” said Paula.
“It’s not a gender bender party. It’s like an initiation to our party group. All new members have to dress up the first time they come. It’s so everyone knows who the new members are. Don’t worry. No one will laugh. In fact, just the opposite. They will all be delighted to see you. If you don’t feel comfortable coming in, I understand. You can leave any time. I hope you will stay though as I’m certain you will enjoy it. What do you say.”
“What do you think Paula?”
“Why not. We are here now. If we don’t like it, we can go.”
“OK. Let’s do it.”
Tony led us through large double doors into an equally large lounge.
As we entered the room, a number of people turned and clapped and there was a wolf whistle as well. That could only have been for me as Paula didn’t look sexy in chinos and a shirt. I couldn’t help but feel a little thrill flow through my body, that someone thought I looked good as a woman.
Almost immediately a couple came over to us and introduced themselves.
“Hi. I’m Zak and this is my partner, Rose. Pleased to meet you.”
“Hi Zak. I’m Harry, and this is my wife, Paula.”
“Come. We will show you around.”
Zak got hold of my arm and led me one way, whilst Rose took Paula’s arm and took her another way.
“Let’s get a drink first,” said Zak.
We went into the kitchen, which was very quiet at the moment.
“What would you like to drink?”
“Whisky would be good.”
Zak poured me a large shot.
“I have to say,” said Zak. “That was a good choice of clothes. That mini skirt really shows off both your ass and your cock.”
I must have looked shocked.
“Sorry. Didn’t Tony tell you this is a swinger’s party. Anything goes. Tony says that if you tell people it’s a swinger’s party they won’t come, but surprise them and they will often stay.”
“I don’t know if it’s mine and Paula’s thing really.”
“If Paula wasn’t happy, would she not find you and say let’s go home?”
“Yes. I suppose so.”
“Well relax then and enjoy the party. If anyone propositions you and your not interested, just say, perhaps later. No one will take offence. And if you would like me to fill that ass of yours, just ask.”
“I’ve never done anything like that. Only straight sex.”
“Not even pegged by your wife?”
“No. But I must admit to wanting to try it. I just didn’t thing she would be up for it.”
“You never know until you ask. Go and mingle and enjoy yourself. Come and find me if you want to take my offer up.”
I could see him looking at my knickers and realised that all this talk about sex had an effect. My cock was trying to find a way out and there was a big wet patch on the front of my knickers. The big glass of whisky that I had drunk quickly was having an effect. I was actually quite enjoying myself.
“Come on. let’s mingle.”
As I entered the lounge I quickly looked around for my wife, but she was nowhere to be seen. I did notice that everyone was looking at my crotch and smiling.
As I wandered about, I got propositioned many times by both men and women but my mind kept going back to Zak and his anal promise. It would be my chance to try anal without any consequences.
Then, as if he could read my thoughts, Zak appeared.
“Hi Harry,” he said. Standing next to me and placing his hand on my bum.
As he did so, a tingling flowed through my body and my cock strained even harder against my knickers. I couldn’t believe I was being turned on by a man.
“Hey, I’ve been thinking Zak about that offer. Can we do it?”
“We can. I knew you would be back. All the bedrooms are busy at the moment, so as it’s a warm night, lets go in the garden. Its dark out there so we should get some privacy for your first time.”
As we walked out my legs were shaking with anticipation. I couldn’t believe I was about to voluntarily have sex with a man.
In the middle of the lawn there was a wooden table and bench. Zak took my hand and led me over to it. He then gently pulled my knickers down, releasing my cock, which was hard as a rock. Zak then sat me on the table and said.
“Let’s relax you first. It will be a lot easier if you’re relaxed.”
He then took my cock in his hand. It was like an electric shock flowed through my body. I cried out in delight and lay back on the table, moaning with pleasure.
As he was massaging my cock the garden light came on and we were flood lit. I realised we had an audience, but I didn’t care. I’d never felt pleasure like this before and I didn’t want it to stop. After a few minutes Zak let go of my cock and took it in his mouth instead. I let out a loud squeal.
There was loud clapping from my audience, as Zak worked my cock in and out of his mouth.
Although I’d had blow jobs from my wife, this was on another plane. Zak knew just how to push the buttons. His tongue caressing and searching the length of my cock, bringing new levels of pleasure.
Then I couldn’t help it. I cried out.
“I’m coming, oh god.”
This brought another round of cheering from my audience.
Then I came in Zaks mouth.
Zak dutifully swallowed it.
Next, I felt a finger exploring my ass. It slid in a lot easier than I thought it would. Then it found my prostate and my eyes rolled back in my head.
Someone then got hold of my hand and place a cock in it. I looked up and saw one of the guys I had been talking to earlier.
He gave me a wink and I started to massage it. Not long after another cock found its way into my other hand.
All of a sudden, I became aware of something bigger than a finger entering my ass. It went in easier than I thought it would.
I let out a cry of pleasure. The feeling of having your ass full of cock was unbelievable.