I have previously related the events surrounding the first time I was spanked by Michelle, and then the events of the second time I was spanked by my own girlfriend, Eileen, when I told her that Michelle had spanked me. It didn’t take me long to figure out that I should probably keep this spanking business to myself unless I wanted to get spanked more. The problem was that there were already three people who knew, Michelle and her boyfriend Tony, as well as my girlfriend Eileen.

It was a beautiful and hot summer that year, and my older brother had almost daily social events at the pool in our parent’s back yard. Michelle and Tony were there regularly. After the incident in which Michelle had spanked me, I was expecting to be invited into Michelle and Tony’s sexual world - the “Land of Fuck.”

Eileen expressed her interest in coming over to spend the afternoon in my back yard. I immediately took her up on the idea and two days after the incident in which she had spanked me, she came over to spend the afternoon by the pool. I was proud to show her off to my brother’s friends. She was wearing a one piece print polka dot swim suit that her mother had probably bought for her at Costco. It had ruffles around her midriff, and a high neckline that didn’t show any cleavage. I was a little disappointed that she didn’t show off her beautiful D cup tits. It was obvious, to me anyway, that she had a large bosom. I kept looking to see whether the outline of her nipples could be detected. She had silver dollar size dark brown nipples that stood out against her very white skin. The thought crossed my mind to pull her top down so that her tits would flop out.

Eileen pulled up a lounge chair next to Tony and Michelle by the side of the pool. She immediately started talking with them. I was sitting across the pool so that I couldn’t hear everything being said, but I imagined that they were comparing notes about spanking me.

As the afternoon went on various people were playing the guitar and singing, while others were splashing around in the pool. One of the women there, Joanne, was a tall, statuesque and athletic looking blonde. I could hardly take my eyes off of her. I imagined that she was flirting with me, but when I went over to talk with her she told me that I reminded her of her teenage son. She didn’t look that old. Thinking back on it, she was probably in her late thirties and clearly in her prime.

I was eighteen years old, six feet tall and weighed about 120 lbs. She was six feet tall, voluptuous, and probably weighed about 170 pounds. Her swimsuit was like vintage French lingerie, such that there was a loose fit around her legs. I kept trying to see if I could catch a glimpse of her pussy. I moved around while we talked, trying to better position myself to look up her shorts, and finally realized that the most I was going to see was a little bit of her trimmed pubic hair.

I got up to join Eileen, Michelle and Tony, but their seats were empty. I left the poolside to go into the house to find them. When I got inside the house I determined that they were in my bedroom with door locked. I got down on my knees and peeked through the skeleton keyhole in the door. They were all naked and Tony was fucking Eileen while Michelle was fondling Eileen’s breasts. I turned the knob on the door to see if it might open, but it was locked. I knocked on the door, announcing myself, and asking them to let me in. They ignored me.

I continued watching through the keyhole. I could hear Eileen moaning with pleasure. Tony turned her over on her stomach and buried his face in her butt cheeks. I assumed he was eating her out, but it also occurred to me that he was rimming her ass – preliminary to anal sex. Michelle was just watching now. I knocked on the door again, but this time Michelle came over and let me in.

When Eileen saw me standing there she told me to take off my swimsuit. Tony was now standing between Eileen’s legs as she lay on her stomach, holding his cock in his hand, and rubbing it up against her ass hole. Eileen seemed to be enjoying it, but when he started to insert his cock into her ass she cried out in pain. Tony stopped trying to penetrate her. He turned her over onto her back and then started eating out her pussy. I was just standing there watching this. I felt Michelle’s hands caressing my butt, but it didn’t turn me on. I was lost in my thoughts, thinking about the fact that Tony was having sex with my girl friend, Eileen.

Michelle guided me over to the edge of the bed, and had me sit down. She kneeled between my legs and started to suck my cock. It felt good, but I wasn’t getting a hard-on. I was still watching Tony and Eileen.

Tony stood up while Eileen remained lying on her back.

I got up, carefully pulling my cock out of Michelle’s mouth and went over to Eileen. I knelt down on my knees between her legs and started to lick her pussy. She had a strong, thick aroma rising up from her cunt. Her pussy was sopping wet. It was hard to tell whether it was wet from her own juices or whether Tony had shot a load in her and it was now dripping out. Whatever it was, it was an intoxicating smell and taste. Eileen’s dark hairy bush was saturated in fuck moisture. I was licking between her lips, rubbing my nose between her lips and shoving my whole face into the midst. As I became more and more excited I thought that I could clearly detect Tony’s cum as part of the mixture oozing between her thighs.

"WHACK." 

Tony smacked my ass. He asked me again whether it was a good idea to keep having sex right now, or maybe wait until later on tonight. I didn’t even begin to try to answer him.

"WHACK!" 

This time he really whacked my ass, so hard that I started to lose my balance.

"WHACK, WHACK, WHACK!" 

I started to stand up in order to stop him from spanking me, but he pushed me down and shoved me forward on the bed. I was on my stomach. He climbed on top of me and started trying to shove his cock into my ass. I squirmed to get away, and managed to get off the bed and stand up.

Tony stood in front of me with a big shit eating grin on his face. Michelle moved behind me, wrapping her arms around me. I could feel her firm tits pushing up against my back. She put her mouth to my ear and told me she wanted to watch me suck Tony’s cock.

Eileen was standing next to me now as well, and she said the same thing to me. She wanted to watch me suck Tony’s cock. I looked down to see that Tony’s cock was hanging between his legs, and was still soft. Michelle pushed down on my shoulders, bringing me to my knees, and Tony’s cock was hanging right in front of my face. I could smell Eileen’s cunt on Tony’s cock.

I turned slightly around to where I was looking right at Michelle’s very hairy pussy. She had her own smell that was very different from Eileen or Tony. I tried to pull her legs open so that I could put my face into her cunt. When her legs opened a little I got a much stronger whiff of her and I wrapped my arms around her, clutching her butt and pushing my face into her pussy.

Tony pulled me off of Michelle. The next thing I knew I was lying on my back on the bed and Tony was kneeling over my face trying to shove his cock into my mouth. Michelle was sitting between my legs and she was shoving one of her fingers into my ass. Eileen was sucking my cock. I relaxed my jaw and let Tony push his cock into my mouth. I began to gag as he pushed his cock in farther. Tony started moaning and I realized he was about to shoot his load into my mouth. As I felt his hot cum sliding down my throat, Eileen's lips at the root of my hard cock, and Michelle's fingers spreading my ass apart, my whole body went into the convulsive spasms of a monumental orgasm.

I must have gone to sleep because when I opened my eyes they were all gone. I was lying on my back, naked on my bed, and Joanne was standing next to the bed, towering over me. She wasn’t completely in focus, but I rubbed my eyes and clearly saw the big smile on her face. I could also, now, successfully look up the bottom of her swim suit to see her bush.

She asked me if I was okay, and it wasn’t until I started to say “yes” that I felt the soreness in my ass. I was simultaneously embarrassed and turned on. I didn’t remember what had happened to my ass except that Michelle had started fingering it. Joanne adopted a very motherly attitude, which was all the more strange because I was lying there naked looking up at her bush.

Joanne then sat down on the bed next to me, taking hold of my hand in a very comforting way. I didn’t understand why she was acting like this until she said, “Tony and Michelle told me what happened. They told me they got a little carried away and were afraid they might have hurt you.”

My butt still felt sore so I reached around with my hand to feel it. My fingers slid over my butt hole and then into it. My butt hole was wet and loose. I didn’t know whether it was from Michelle’s fingers or from Tony's cock. I asked Joanne, “What did they say happened?”

“They said that Michelle stuck her whole hand up your ass and then Tony fucked you,” Joanne answered.

Joanne looked at me very compassionately. She stood up, took off her swim suit, and laid down next to me, our naked bodies in a spooning position, with Joanne behind me.

“Did they say anything else?” I asked.

“They said they were going out for a pizza and to tell you they would bring some back for you.”

I fell asleep in her arms.