I've been dreaming of this day for years. I've been watching bisexual porn and using toys for what feels like forever. I'd gone to video booths with glory holes and either didn't find anyone, or chickened out before taking the plunge.
It was about a month ago when I first started interacting with her online. It was not a focus on having sex with her, though our conversions did have sexual topic focuses. She was the most open and real person I had met online. She was encouraging of my self discovery and kink exploration. She encouraged me that there are women out there who enjoy bisexuality in their men.
It happened during one of our conversations where she asked about my post advertising wanting to meet a couple. I shared that I was giving up on the gloryhole angle and was going to make my focus finding a local couple that would be a good fit to make my first time a reality, but also a great experience.
She said that while she was not local to me, she and her husband were planning a vacation in a month that would have them not too far from me. She said she and her husband would love to give me my first experience.
I was taken aback and took a few minutes to respond. I said that would be amazing. I had seen many of their pictures and activities, even masturbated to thoughts of being with them, but never considered that would ever be possible.
We started making plans. It was decided that I would come join them for lunch during their visit to make sure we were still compatible in person. She said that if they felt comfortable with me, she would invite me up to their room to show me some outfits after lunch. She said all I had to do was agree and they would take things from there. She must have stressed a dozen times leading up to the lunch that nothing would change with us if I declined her invite.
As the day grew nearer, my nerves went into overdrive. The morning of, I could barely function. I must have thought at least three or four times about not going, but fortunately I did go.
When I got there, they were waiting with a table already. She looked beautiful. She was wearing a cute sun dress. Her husband was dressed in slacks and a polo. He looked quite handsome. We made small talk over lunch. It was mundane and comforting. My nerves shot up as I could tell lunch was coming to an end...would she invite me up? I had already made up my mind. I saw her look over at her husband and detected a slight nod. She smiled and looked to me and said she had some dresses she wanted to show me, if I wanted to come take a look.
I nodded, I couldn't find my voice. She gave a little laugh. She told her husband to take care of the bill and come up in about 30 minutes.
When we got to her room, she said I really do have an outfit to share with you. She pointed to the bed where a sexy black panty and bra set were laying, along with stockings and a slutty looking top with a mini skirt. I swallowed a little too loud and she put her hand on my shoulder.
"Let's get you dressed up and see how you look."
She had me undress. I was so nervous, even being with such a sexy and confident woman, my penis was soft and trying to hide. We got me dressed up, I finally got partially aroused as I was finishing with the outfit. Next she sat me down and did my make up.
"A man loves his gurls to be sexy."
She did my nails too and changed my hair a little. When she was done, I couldn't recognize myself. I could still tell I was a guy dressed up, but I did look like a sexy sissy slut.
A few minutes later, her husband returned. He gave me several compliments on how sexy I looked. He was looking at me like I was someone he wanted to devour. I started shaking a little. I wanted this, I wanted him, but nerves are a bitch.
He went and poured all three of us a drink and his wife and I sat on the couch while he sat in a chair positioned across from us. The drink was strong enough to help my nerves, but not so strong that I was going to be drunk.
She put her drink down and said it was time to learn how to please a man. She had me stand up and her husband came in front of me. She stood behind me and grabbed my hands. She guided me to start rubbing his chest and arms.
"Feel his muscles, know that those arms are going to soon be controlling you," she whispered in my ear.
"When you are ready, pull his shirt out of his pants and start to take it off."
She let go of my hands and I continued to run my hands over his chest and gave a small squeeze as I felt his biceps. I let a soft moan out as I reached down to pulls his shirt up.
His hands touched mine as her grabbed the bottom of his shirt. It gave me goosebumps, I wasn't prepared for that. I let go and he swung his shirt over his head in a fluid motion and tossed it aside.
He wasn't a muscle bound fitness freak, he had a dad bod, but damn if he didn't look sexy. I understood a little better how such a simple act can cause someone to be aroused.
His wife whispered in my ear, "He likes to have his nipples sucked. And make sure you run your hands along his back and waist."
I did just that. I felt his chest rise as my lips met his nipple. I felt his hands grab my head and lightly pull it against his chest. My hands felt up and down his back. As I slid my mouth to his other nipple, I let my hands trace along his waist. He sucked in his stomach a little. I knew from experience that a man does that when he wants you to go lower. I was surprised at how horny that little action made me.
I felt her hands give a light press downwards on my shoulders. I felt myself slowly drop to my knees. I reached out and placed my hands on his ass and gave a light squeeze and pulled him a little closer. I moved my head to his crotch, I could tell he was hard. I kissed the hard on through his pants. I was burning with a desire to see his cock. I needed to see it
Somehow I managed to go slower than I was thinking I would. I undid his belt, followed by his pants and zipper. I felt his cock twitch as my fingers grazed him as I lowered the zipper. I reached up and grabbed his pants at the hips. I paused as I considered whether to do pants alone or underwear too. I thought to myself that I now knew one reason women always seemed to pause. It wasn't just enjoying the moment, but deciding what's next.
I opted to remove both. I slowly worked his pants and underwear down. I stared at his crotch, loving the look as his shaft came into view, being pulled down by this underwear. When his cock sprung free, I let out a little gasp. It looked perfect. Not so big as to cause fear, and definitely not too small. I saw a small bit of precum on the tip. I resisted the urge to just grab him right then.
I continued pulling his pants down and held them as he placed his hands on my shoulders to step out of his pants. Just the presence of his hands on me caused tingles. I'm not sure exactly when it happened, but I became aware of my own cock starting to leak into my panties.
I reached up and gently grabbed his cock. If felt hot, hard, soft, all at the same time. I looked at his cock in my hand and gave it a slow stroke, watching more precum leak from the tip. It was at that moment I froze.
