The evening was going so well. Before meeting Gary I had these fantasies I played in my head of how my first time getting fucked by another man would be. After several attempts of trying to meet other men and then me chickening out at the last minute I finally found someone who I felt comfortable meeting in person.
We chatted online about three times before I finally felt comfortable talking to him by phone. Those three online chats were each like two hours of conversation. He never pressed trying to meet me. Matter of fact I was the one that wondered if he opposed the idea of exchanging numbers. He reassured me that he had been wanting to meet for real since our first online chat.
By this point he sounded like someone that understood that my first time I would need to be eased gently into sex and he sounded patient. I even asked if he would be ok if I changed my mind at the last minute. He was so understanding and said that we could just talk and keep it non-sexual if I wanted.
I just turned eighteen and Gary was thirty-one, so at first I discounted him because of his being more than ten years older than me. But sometimes you just connect with someone even if at first they don't seem to be the most ideal person.
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Now I found myself with a cock in my ass while trying to hide my face from the person that had just walked into the apartment.
I felt embarrassed because I didn't want anyone to know my fantasies to be with another man, let alone to be the one that took a dick inside my ass.
I had finally grown comfortable with the idea that Gary knew who I was - yeah I know... after only three online chats.. What an idiot I am!
Nonetheless, mentally I had grown comfortable with the idea of letting this man fuck me before I met him. If he's the only one that ever knew about my wanting to be with another man, then I guess I am willing to try this out.
He told me his roommate was out of town and that we wouldn't be bothered. He said that no one would know.
But now, here I was leaning over a couch while Gary was pressed up behind me working the fullness of his seven inch cock inside me. I was starting to lose myself in the moment hearing the music of Lady Gaga's "Edge of Glory" playing in the background when Gary's roommate walked in on us.
My face was turned towards the door as my hands gripped into the soft leather of the couch. Each gentle thrust he pressed into me made my body push further into the soft leather cushions of the couch while my fingers kept gripping tighter with every stroke he worked into me.
I don't know how I missed the latch on the door turning as his roommate unlocked the door, but it was hard to focus on anything else at that moment. I didn't even notice the front door opening. It wasn't until the door was fully open and I saw a brand new face staring straight at me. It kept smiling at what I can only imagine was a stupid cross-eyed look on my face which was the result of an ecstatic filled moment of sexual anal pleasure.
My eyes widened as I quickly realized there was a third person that was now in Gary's apartment. I turned my face away from the door towards the other side of the living room as though me not seeing this third person would make this moment go away.
"Oh shit, oh shit," I said out loud.
All I could think was that I didn't want my friends and family to know about this. Now, EVERYONE will know!
My mind began to process the unwelcomed idea that now I would be exposed to my family and friends, while I kneeled there in this vulnerable position, nude, with another man's engorged penis in my ass.
"Oh hey Gary," his roommate said in a very casual voice with no surprise in his tone.
"Hey Desmond," Gary replied also very casually.
"Don't mind me... you kids finish up what you're doing."
Still petrified, I hadn't moved a muscle. I still had my face turned away from this stranger, hoping that he didn't know me.
I heard the front door close, but by the shadows on the wall I was facing I could tell Desmond was still there. I wanted to admonish Gary for not having dead-bolted the door, but for some reason my body was frozen and just wishing that Desmond would go away.
"Is she ok?" Desmond said.
"She's fine, I just think you startled her," Gary said as he patted my ass.
"What the fuck!?" I thought to myself. Were they referring to me as "she"?
All of a sudden I felt this humiliation. They were referring to me as "she" and talking as though I couldn't hear them. Yet, I still couldn't make my head turn back towards the roommate nor could I find it in myself to push Gary off of me.
"It's ok baby," Gary said to me as he bent further over me and pressed his body on top of me to whisper in my ear.
It must've been no more than ten seconds in this whole interaction, but it felt like minutes had passed by as I was waiting for Desmond to hint that he would go to his room or to just go away.
The whole time Gary never stopped his stroking motion as he proceeded to fuck me. And he seemed to get even harder. I didn't think he could get any harder, but I felt the stiffness of his cock get even more rigid.
"It's okay baby. Desmond likes to play too. He doesn't judge anyone and definitely won't judge you," Gary reassured.
I wanted to tell him, it's not him judging me that I'm concerned about. I just thought that this secret would be mine and Gary's. Now a third person I hadn't counted on knows about me without my approval.
Desmond proceeded to chime in, "yeah baby girl. I won't judge you."
I still didn't turn to face Desmond hoping he would go away. Maybe once he left to his room I would find it in myself to push Gary off of me, get my clothes and get the fuck out of there.
I could see movement of Desmond's shadow on the wall, but instead of disappearing from the wall it seemed to get bigger.
"Fuck, he's coming towards the couch. He's not leaving," I realized.
I began to push off the couch. The couch was so plush and cushiony that my hands and arms sank deeper into the couch before I could start to feel any leverage to push away and eventually push Gary off.
Also, Gary's upper torso was still fully pressed on my back from the moment he leaned in to whisper to me, so I didn't have as much leverage to push him off as I hoped. As I did this, I felt Gary's weight fight against me a bit as though he was purposely working to keep me pinned against the couch.
I began to get scared at that moment. It's rare for a man like me to feel helpless and not in control. Sure, I had a dick in my ass, but I allowed that dick to enter my ass. Now I was starting to feel like maybe I was being forced. A rare feeling of fear from lack of control and inferior strength started to make my mind race with scary thoughts.
Desmond made his way behind the couch and reached for my chin with his right hand.
He pulled my chin and lifted my face to look at him. I couldn't see him very well because there was light in the ceiling just behind him. From my perspective at that angle he looked more like a big shadow. He must've been about six foot five and a husky build. What you would call a barrel of a man. In that short amount of time he had already undressed himself and was only wearing his boxer briefs.
"Don't be shy, baby girl," he said.
"Fuck." I thought to myself. "There he goes again calling me 'baby girl'. I'm a fuckin'man," I thought to myself. "A naked man with a lubed up cock inside him, but still a man. Not a girl."
Even though this thought went through my mind I didn't say anything out loud. I was at a disadvantage. I was in survival mode now. I thought, "okay, I already have a cock in my ass, so it isn't like they can rape me. But if they got really rough they could end up hurting me. And if I talked shit, they could end up beating me up. Shit! Shit! Ok, just go with the flow. Try to get out of this."
"Hey honey, are you ok," Gary said. The tone in his voice had a genuine note of concern.
"I think she's scared," Desmond replied. "Hey, we just wanted to help you with your fantasy that you talked to Gary about."
Just then, I remembered talking to Gary online about one of my fantasies. I always wondered what it would be like to be in a helpless situation where I was made a fuck toy by two men.
I fantasized about what it would be like to be used and submitted and even humiliated.
Gary was still pressed up into me.
"Hey, if you want us to stop, we can stop," he said.
I believed Gary as soon as he said that.
I looked back up at Desmond who was standing over in front of me. I could see him a little more clearly as my eyes adjusted to the light behind him. He was good looking with blue eyes. You can tell he worked out, but he wasn't your typical toned and cut gym monkey.
He had a muscular hairy chest. Thick muscular arms and even though he wasn't thin, you could see the top 2 muscles on his stomach with a slight belly. Very slight belly. His stomach still looked rock hard, not flabby.
He leaned down to take a better look at my petrified face.
