A Surprise Blind Date

This is my first story in a while. I've tried to take in feedback from past stories and incorporate into this one. I hope you enjoy!

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I'm Barry and this is a story about a trip to a party that took a very unexpected twist. There's an old story about a frog who jumps in a pot of water on a stove. The water slowly gets hotter until the frog realizes too late that the water is too hot and is boiled. In this case the frog is me and the pot is a hot tub!

I had been working in a nice office in a quiet suburb. It was a great job and I worked with a very attractive younger woman named Lisa. She was blonde and very athletic. I had just turned 40 and started to show it. I had gained weight and had lost confidence.

Lisa was my assistant. She didn't actually work for me but I was supposed to be mentoring her. I had developed a crush on Lisa and masturbated thinking about her.

It was a small office and everyone knew everyone so there were very few secrets... except to someone like me who worked alot. I was relatively new in the office and had few friends but Greg was one of them. He seemed nice and tried to help me fit in. He was probably 30 and a nice looking guy. In great shape and very confident.

He asked me to lunch one day and we talked. Greg led off by asking me about people in the office. I should have known better but wanted to make a good impression on him and wanted to be "one of the guys." He was very direct.

"So that Lisa is a real looker, eh Barry? I don't know how you get any work done around her."

I tried to downplay it; "Oh I suppose she's good looking but shes really a good worker and very nice."

Greg didn't believe what he was hearing.

"Are you shitting me? Shes amazing looking! Don't you think she's hot?"

I didn't want to risk a "HR moment" so I said "no." He just shook his head. I didn't want to tell him I had a huge crush on Lisa.

A couple of days later Lisa came over and said "Hey I'm having some people over this weekend. Why don't you come over?" I couldn't believe my ears!

I saw no reason not to so I decided to go for it.

"Sure!" I said.

As the day approached, all of a sudden I got a bit nervous. I have a very small dick and what if somehow Lisa sees it? I decided to just see how things go and not worry about it.

So the big day arrived and I went to Lisa's place. She was friendly as she opened the door.

"Come on in Barry!" she said. She had on shorts and a swim suit top. She gave me a beer and I nervously drank it quickly. Then I grabbed another one. I came to the patio and saw there only two others at the party. It also dawned on me that I was way overdressed; I wore Khakis and a button shirt. The others wore swim suits and loose fitting T shirts.

Greg was one of them. He had on a bathing suit and a tank top. He had a really nice build.

The other guy was named Steve. He was tall, well built and black. Steve had on a tight speedo that left nothing to the imagination.

"Steve just broke up with his boyfriend," said Lisa.

"I was too Alpha for him." Steve shrugged.

I wondered if anyone else was going to show up. I also wondered if I was somehow being paired up with Steve. Or were Greg and Steve together? Did they think I was gay? I thought back on the conversation with Greg about Lisa and thought maybe that explained why. I drank a couple more beers to try and calm myself down.

"Let's all get into the hot tub!" said Lisa.

I wasn't sure what was going on but after several beers my defenses were lowered. One of my issues was clothing; I didn't have anything to wear. Also I had developed man boobs and was worried about showing them. But Lisa had asked so I decided to join in.

I started by taking off my shirt and Lisa giggled. "Nice rack! What are you? A "B" cup?"

Greg had slipped in next to Lisa and I mean right next to her. Steve motioned me in but i had to take off my pants first. I had on white briefs that I knew would show how tiny my dick was when wet. But I figured I would worry about that later. I pulled down my pants and kicked them off. Then I quickly got in the hot tub next to Steve.

I looked over and my heart sank as I saw Greg put his arm around Lisa and they kissed. Steve sighed. "God that's hot isn't it? I'm so lonely right now. Are you seeing anybody Barry?"

"Nope" I replied. I didn't want to admit it but my last girlfriend pretty much kicked me out for being a "shitty lay" as she called it.

"Well I think youre cute" said Steve. "You're just my type". I felt his hand on my thigh and he started rubbing. It felt pretty good to be honest so I let him continue. Then it hit me what was going on and I got defensive and thought it best to get out of the hot tub. Not wanting to get up I asked Steve if he could grab my clothes.

He got out of the hot tub and I couldn't believe my eyes. I could see the outline of his massive dick through the wet speedo. I couldn't take my eyes off it.

Steve could sense my interest. As he tried handing me my clothes he dropped them "accidentally" into the hot tub!

"Shit I'm sorry baby" he said.

Lisa then chimed in.

"Well Barry you're too big to fit into Greg's or Steve's things. I've got some baggy tops you could wear while your clothes dry out."

"Wait I cant wear your clothes Lisa!" I stammered.

"Why not? Do you guys mind?"

Both Greg and Steve shook their heads no.

I sheepishly got out of the hot tub hoping nobody would look at my little dick but of course they all did.

"At least you don't appear to have much to cover up." Lisa snickered.

Lisa took me by the hand and led me into her place and into her bedroom. The place I had dreamed of so many times while jerking off. But real life was turning out to be far different from fantasy.

Lisa took on a whole new personality once we were alone in her bedroom.

"Ok first lets drop the pretending. You're obviously a sissy otherwise you would have at least made a pass at me. Greg told me about what you talked about at lunch."

I wanted to argue the point or at least explain myself. But it dawned on me that she was right. I was attracted to Steve and honestly I couldn't wait to be with him.

"So lets start by you taking off those underpants."

She walked over and yanked them down.

"Oh my God! That is the tiniest dick I have ever seen! I think you're more girl than boy. I'm calling you Sherry from now on! Now I want you to be sexy for Steve. He loves sissies like you but before we get you dressed up, I want you totally hairless. Put this on all over. Wait ten minutes then rinse it off. Then put on this moisturizer and come out here."

I didn't want to argue with her. I knew she was right. I went into the bathroom and did as I was told.

I came out of the bathroom naked and now hairless. She handed me a pair of panties and I immediately put them on. She then handed me a very girly cover up. I put it on right away. I must admit it felt very sexy on me.

"You wont have these on very long if you seduce your man the right way," Lisa said.

"No shit!" said Steve, who was now standing in the doorway watching everything.

"I'll leave you two alone Sherry. I'm going to go and fuck Greg!" said Lisa as she walked out and closed the door.

Steve came over to me and kissed me hard on the lips. He then put his hands on my shoulders and gently pushed me down to my knees. I didn't need any instructions on what to do next. I reached out and pulled his speedo down.

Steve's cock hung almost halfway down his leg. I licked my own lips then started to lick this amazing dick. As it began to harden I picked it up with my hand and couldn't believe how much it weighed.

"You know what to do Sherry. You're a natural cocksucker aren't you girl?" asked Steve.

I didnt have to say a word as I started sucking. It really seemed like I belonged on my knees performing this act of feminine submission to my new man. I wanted ... no needed... to please him. As I sucked I could feel him tense up and he unloaded a huge load of cum into my mouth. I swallowed every drop relishing the new life I had encountered.

To be continued?