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Rachel, my college roommate, has been my best friend at college ever since we first met as assigned roommates our freshman year.
We've always gotten along very nicely though she is a bit wilder sexually than I am. We never talked about the details of her sex life, but once in a while I noticed evidence that she was willing to do a lot more than I ever would. The most blatant time this happened was once when I heard her get up in the middle of the night and leave our dorm room. For some reason which I still don't know, I got up after a bit to check on her. I wandered quietly down the hall and heard something in the lounge. The lounge was darkened but the television set was still on, though the sound was turned low. I quietly went into the lounge, and looked around the corner into the back of the room. The first thing I noticed in the low light was Rachel, totally nude, on her knees, facing away from me. Then I noticed that she was kneeling in front of a guy, apparently sucking his cock. He was fully dressed, and as I said, she was completely nude and on her knees. I quickly and quietly backed out of the room and stood there in shock. They apparently didn't see me--Rachel since she faced away from me and I presume the guy had had his eyes shut. Perhaps you've guessed that that is not the sort of thing that I do. I went back to our dorm room without revealing myself and never spoke to Rachel about the incident. Though it was a shock, I managed to keep it from affecting our friendship.
Recently, I brought Rachel home for a weekend visit to my home town. After dumping our bags at my mom's, I took her out along with two of my best high school friends, Clara and Jack, who have been married since just after graduating from high school. Back then, I had always admired Jack, but he and Clara had been together since 8th grade. Well, that night the four of us stopped at a bar and had some drinks and Rachel hit it off with them immediately. She has always been able to "hit it off" with people, and in fact, can make me feel like she knows my friends better than I do after just a few seconds of conversation. After that, we went to a club and danced some, then Rachel and I came home and had a couple of more drinks with my mom. It wasn't overly late when Rachel and I retired to my room and went to sleep. However, I woke up in the night and noticed that Rachel was gone. Just like back at the dorm, something made me go search for her. I walked into the living room and received the shock of my life! Rachel was across the room sitting down and was partially nude, and Mom was kneeling in front of her, sucking on one of her breasts! I couldn't believe my eyes! Rachel was wearing just a pair of cutoffs, showing her slender body and small breasts, and had a wicked smile on her face. Mom was wearing a nightgown and was making little slurping sounds as her head bobbed. "Mom!" was about all I could blurt out as I rushed over. They continued, apparently oblivious to me. "Mom! How could you!" I said when I could speak again. "Your mom is a frustrated lady" said Rachel, "She hasn't had a man for quite some time, so let her be." I couldn't believe this was happening--I knew Mom hadn't dated much since her divorce years before (in fact I didn't recall a single date) but I certainly didn't know she had any bisexual tendencies!
After a few minutes, Rachel gently pushed my Mom away from her breast, smiling at her, led her into the dining room, and gently guided her into leaning forward over the dining table so her toes were on the floor and her body was face down on the table. "Get my purse", Rachel said to me. As if in a dream, I went and got it and handed it to Rachel, who opened it and drew out some K.Y. jelly and a dildo. She lifted Mom's nightgown up to her waist, which left Mom's ass bare since she was wearing no panties. Then she started smearing K.Y. jelly on the crack of Mom's ass! She rubbed it and started pushing it into Mom's rear hole with her fingers. Then she took the dildo, and after smearing it with K.Y. jelly, started pushing it right into Mom's ass! All this time Mom hadn't said a thing, but when the dildo entered her ass, she started breathing hard and grunting through clenched teeth.
Part of me was stuck in shock, but part of me was fascinated by the hedonism and I realized that I was really turned on. Rachel kept moving the dildo in and out of Mom's ass, but she said to me "You haven't had a man lately either, have you?" It was certainly true, but I stood there, mute. "Lay down next to your mom and I'll bring you off" said Rachel. A whispered "no" was all I could muster. "I won't do this," Rachel said, referring to what she was doing to Mom, "I'll just use my fingers on your cunt. You're hot, I know you are".
With that, while continuing to work the dildo in and out of Mom's ass, she put her other hand on my ass, slipped it underneath and rubbed my cunt with her fingers through my panties. I couldn't believe the sensation, and was breathing hard in no time. "Lean over the table like your Mom" she said, and I did. She lifted up my nightgown and pulled my panties down to my thighs and started massaging my cunt in earnest. With my hands, I held the opposite edge of the table, and I looked at my mom, who was looking the other way. From the rise and fall of Mom's breathing, it seemed that she had come a couple of times and I was getting close. Then the messaging stopped, and soon I noticed Rachel was putting something on my wrists. It was handkerchiefs, and somehow (with some rope, I think), she tied it over the opposite edge of the table so I couldn't get up. I noticed that my ankles were somehow restrained too. Then she started fingering me again, but stuffed some cloth in my mouth while she was doing it. Then the doorbell rang!
I had no idea who it would be in the middle of the night, but Rachel went and answered it, and Clara and Jack came in! I looked at them and almost died of embarrassment, but they didn't seem surprised though they looked a bit amused. My mother stayed where she was, though I couldn't tell if she were tied in that position the way I was.
"Yes, she's dying for cock" I heard Rachel say, and Jack came up behind Mom. Jack took off his pants and pulled out his cock. "I just did her ass; her cunt deserves some attention". Jack's cock was rock hard, and he started pushing it into Mom's cunt. I noticed that Clara was just standing there, watching interestedly. Then, Rachel stepped out of her cutoffs, got up on the table in between Mom's arms, and sitting on her rear on the table with her hands and feet on the table, scooted her cunt right up to Mom's head. With one hand, she pulled the cloth out of Mom's mouth, lifted her head, and pushed her cunt right into Mom's face. "Lick it, slut" she hissed. I squealed through the cloth stuffed in my mouth, but I'm not sure what I was going to say. On and on they went in silence until Jack came, Mom obviously coming too. Rachel, I couldn't tell, though she seemed to have enjoyed it. Then Rachel stuffed the cloth back in Mom's mouth and the three of them left us, going into the living room, and talked as if nothing like this were happening.
Later, they came back, and Rachel said to me "Now it's your turn, slut." Jack came up behind me and started smearing K.Y. jelly on my ass! His fingers probed and pushed, putting more and more fingers in, while I was just about dying of the sensations. Then I noticed that Clara was nude and was getting on the table in front of me just as Rachel had done my mom before. She took the cloth out of my mouth just as Jack pushed his cock right into my ass. My "Oh" got muffled as she slid her cunt right up to my face. "I've been waiting years to see this" said Clara and I couldn't believe that this had been my high school friend! My body, which seemed to have a mind of its own, pushed back against Jack's cock, and I licked Clara's cunt with abandon, though I'd never even thought of doing such a thing with any woman before. In just a little while, I came and came and thought I was going to black out. Jack had come to, as had Clara--there was no question of that, as there had been with Rachel earlier.
Afterwards, they stuffed the cloth back in my mouth, untied Mom, and took her away to her bedroom. A couple of minutes later, Clara came back, took the cloth out of my mouth, and untied me. While I was stretching and rubbing my arms, Jack and Rachel brought Mom back out of her bedroom. She wasn't in her nightgown any longer, but was wearing a black bra and high heels, and nothing in between! I immediately noticed what a gorgeous body she had, something I was aware of, but didn't see too often. There was a scarf tied around her head as a blindfold, and between her teeth, she was holding a small whip! "See your pretty mom?" said Clara, who led me into the living room over to where Mom was standing. They turned Mom around, facing the wall, and placed her hands up against the wall as if she were under arrest. Rachel took the whip out of her mouth and brought it over to me. "I think your mom likes other things too! Do you want the honors?" and she held out the whip to me! "What are you doing?" I asked, though it was perfectly obvious. "Oh, she wants it, all right" said Rachel; "Do you want to be whipped?" she said to Mom. "Yes" was the whispered reply. Rachel whipped her ass once, and Mom jerked when the whip stung her, but she remained there in the same position. The Rachel handed me the whip and guided me behind Mom. She whispered in my ear: "After your mom gets it, you're going to get it next." She took my arm and swung it around so the whip hit Mom's ass, though not hard enough to do anything. "Say 'whip me'" said Rachel, in a stern voice. "Whip me" was Mom's whispered reply. I gave her a little, half-hearted slash, then started whipping her for real. "Yes!" said Rachel, as I continued, harder and harder, soon watching Mom's ass jerk at each slash. Rachel finally stopped me and pulled me away. "Will you have to be tied down or will you take it like your Mom?" she asked me. Once again, I couldn't manage to get an answer out, just a mumbled squeak, but I had no idea what my answer would have been had I been able to talk. "Grab her", said Rachel, and Jack and Clara immediately grabbed hold of me and pushed me over the back of one of our stuffed chairs, with my ass in the air. They held me down, and a sharp sting let me know that Rachel had started on me. She stopped after a couple of slashes and announced that she was going to give me ten more. Then she gave them to me, one at a time, pausing several seconds between each one. I could not help but count them to myself. Then, just as soon as I relaxed after the tenth slash, she whipped me again! "That was a bonus" she said. "Put them to bed" she said after that, and Clara and Jack led both Mom and me into my room and us both in my bed!
Well, I just lay there, wondering. I thought I heard other things going on in the house, but I didn't get up to investigate. All in all, that night, and the rest of the weekend was the most amazing weekend I've ever spent, and since then, it pops into my mind whenever I play with myself.