I met him on Grinder. Of course. He was cool with me wearing lingerie when we fucked. He said I could do anything that got me off. I shared many of my dreams and fantasies with him over the months we hooked up. I wore all sorts of different outfits, trying to find something he liked. He was okay with it, but I could tell he could take or leave the girly clothes. After some kissing, he would push my face into his ass and order me to lick it really deep while I jerked him off. That was the usual drill. He loved me licking and eating his ass. Pretty much every time he would roll over just before he came and let me suck him till he blew a big load in my mouth. I took it all in stride. I'd get home and jerk off later.
After a while the routine started getting a little stale. I showed up one afternoon, dressed like a naughty nurse this time. But today he had a big rubber butt plug and a roll of tape in his hand. I asked if he wanted it inside his ass. He said "Oh no. This is for you, my little bitch."
He hadn't called me 'bitch' before. Or really hadn't spoken much at all. This was a nice twist I might be looking for, I thought to myself.
"Sure. Whatever gets you off." I said reluctantly.
He led me back into his bedroom. We hadn't used that room before. Usually, we just did the deed on his couch in the living room. He told me to reach out with my hands together.
"I'm going to tie you up and gag you. Then I'm going to get this dildo inside you. So shut up and do what I tell you."
He didn't ever talk like this with me. Another change. I was getting nervous. But I put my hands out anyway. He quickly ripped off a long piece of tape and wrapped it several times around my wrists. The feeling of giving up and letting him bind me was overwhelming. My head began to spin. What the fuck was I doing? The sticky tape secured my wrists tightly together. I was helpless now. I was in a daze.
I think I really like it!
"Good boy." He whispered. He produced a washcloth rolled up into a ball. "Open your fucking sissy ass mouth." I was up one more level of nervous.
I reluctantly opened. He roughly stuffed the washcloth in. My cheeks puffed out. It wouldn't go all the way in. There was too much. I grunted. I wasn't liking this at all. But it was too late. A long piece of tape over my mouth and around my head. Then another.
"Mummph!!!"
"You're a good little bitch. Get on the bed."
I stumbled over to the bed and sat down. He motioned for me to lie down on my back. I obeyed. A handful of nylon rope appeared. He tied my hands up to the headboard. Then tied each of my ankles out to the food board bed posts. Spreading my legs wide apart. When he was satisfied that I was secure, he got on his phone and texted someone. I was getting really nervous now. I attempted to cry out, but, of course, I was too well silenced.
"Don't worry, bitch. I'm just going to break you in with this, then I'm going to fuck you. Then one of my friends is coming over, and he is going to fuck you too."
I suddenly realized how helpless I was. And in trouble. How could I have been so stupid? Dressing like a girl? Letting him tie me up? I barely know this guy. But, as I already mentioned, it was too late.
He used a lot of lube on the butt plug. Sliding his fingers inside me. After some pushing and spreading of my cheeks, it finally slipped in. It's a strange feeling getting penetrated. And it was my first time. I let out a girly squeal. He just laughed.
"Get used to that feeling. You're going to feel it a lot today, bitch."
He took off all his clothes and laid on the bed next to me. His cock was already pretty hard. He used more lube to get my cock and balls nice and slippery. He stroked my cock for a while. Then he pushed on the butt plug. It was all the way in but still could be shoved inside a bit more. He worked it in and out while he stroked my cock. He played with my bra, pinched my nipples, and kissed my cheek. He seemed to enjoy playing with the cute little nurse outfit I had on.
"I think I'll wait for my friend before we fuck you. I've got a better idea for right now."
He climbed on me, straddling my chest. His cock between the cups of my pretty little white and red lace bra. He squeezed my chest together using my perky boy tits and the lace bra to pleasure his cock. It didn't take too much time. He was ready. He blew a big, long stream all over my chest and up under my chin. The bra was wet, as was the front of me. He moved up a bit and blew one more stream all over my face. I struggled. He squeezed his cock one more time, sending a finishing spurt on the lacey white bra.
"That was fucking great, you bitch."
He relaxed next to me for a bit. He played with my tits and rubbed the lace outfit I was still barely wearing.
"I like this one." He said in approval.
There was a knock on his door. He smiled. "Now you're going to get it, bitch."
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