About 10 years ago my girlfriend at the time and I were at a 4th of July BBQ. She was 20, Hispanic, 5'0", 100 lbs or so, very cute figure. Nice big boobs, which she complained were too big for her height. She was rather sexually conservative, but when she drank, she loosened up.
She had been drinking wine coolers (Yech, remember when they were popular?) all day and she was obviously getting pretty drunk. Wearing a very sexy bathing suit, she was attracting much attention. When a buddy commented on it to me, I smiled and said that maybe I should let him get a closer look.
Most of the people had left the BBQ and my girlfriend was on a lounge chair half-passed out. The hostess said I could put her to bed in her room and I carried/walked her in. She was so drunk she couldn't even talk. I set a few dry towels under her and laid her face down on the bed and closed the door.
My buddy caught me outside and asked about her and I showed him where she was. "Pretty tempting huh?" he said. I realized what he was thinking. We both stepped into the bedroom and locked the door.
He said he didn't have a condom and there were none in the bedroom drawers. "Oh well, she's going to have to get it sooner or later," I said.
She barely moved as I peeled her bathing suit off. She was out cold. I put my hand over her mouth and eyes in case she awoke and invited him to fondle her. He lay next to her and caressed her breasts, stomach, and pussy. Still, no response. No way we were going to get her to go along with us.
He and I rolled her back onto her stomach and I began fingering her pussy and ass. He had dropped his shorts and was playing with himself. I had never seen a man do this, and it aroused me. I told him, "We're going to have to fuck her in the ass".
"Has she done it before?" he asked, and I told him no. I had tried before, but she always fought me. This time, she couldn't resist.
"We need to lubricate her," he said, and I searched for some lotion to put on her. I found a bottle of baby oil which I squirted on her anus. she stirred slightly. He was continuing to jack off, but wasn't as hard as he needed to be. "This isn't going to be easy," he said. I started to finger her asshole when she stirred again. He was getting a little harder, but still not enough.
"Bring it here," I said, and he brought it to within inches of my face, fingers, and her ass. His cock pressed up against my hand as he guided it to the rim of her asshole. I put my arm on her back and up against the back of her neck.
"I'm going in," he said. I felt her move downwards as he slowly entered her. She moved again. She made a crying sound, and I told her it was okay. She started moving her body as if to throw him off, but the weight of him and me on her rendered her helpless. I held her face down in the bedding so as to control her and also to not let her know it was someone else (she had never liked him).
She whimpered more and more as his thrusts became more powerful. She finally mumbled her first words... "NO, STOP, YOU'RE HURTING ME," which we both smiled at. He picked up his pace and her resistance weakened. He jerked violently several times, and I could tell he was cumming in her.
Afterwards, he rolled off her and she lay still. My cock was half-hard and I thought about doing her. Then I looked down and he was looking at me playing with my cock. "Need some help?" he said.
I nervously nodded yes. In a second I felt my cock in his mouth, sucking very gently. I was soon very hard and he stopped and pulled away. "Either her or I are going to get it in the ass, you decide!" he whispered.
That was too much for me, and I moved up alongside her. He held her back and head while I guided my cock to her cum filled anus. I entered her and she was very well lubricated. She cried that little whimper again, trying to push me off, but she didn't have a chance. I came pretty quick and cleaned up. As I was dressing we heard someone trying the door. It was Frank, the owner of the house and the host. We let him in and he could see what we had done. Of course, I offered to share the spoils.
He dropped his trunks and quickly a 9" or so cock appeared. "This will wake her up," I thought, and my other buddy and I held my girlfriend down while Frank invaded her.
She put up more of a fight, whimpering and making gasps of pain as his hard cock forced itself into her aching ass. She finally passed out and fell limp. After Frank filled her up, he asked if he could invite another guy to join us. How could I say no?
Before the day was over, she had been anally violated by four separate guys, me included. I left her there and came back later and she looked dead. Big welts and red marks on her ass, backs of her legs, and her back. The sheets were soaked with sweat and cum. She was out like a light. I covered her with a blanket and left her there.
The next morning she woke up mighty pissed. "How could you do that to me, you asshole? You raped me!" She got over it, but whenever she saw my buddy she never knew what he had done to her.