Fiction
A few months after our little adventures, Dee's friend Cheryl called, her daughter was engaged, and she needed Dee's help to plan a bridal shower and help the maid of honor plan a bachelorette party. Dee was overjoyed to help, as she does event planning.
They sat down with the bride to plan the shower, later, Cheryl, Dee and Tracy started to plan out a bachelorette party. They decided to have both on the same day, and to help things out, they were going to rent the penthouse suite of a fancy hotel (Dee knew the manager and got a discount), it had a huge sitting area, dining area, and 3 bedrooms.
A few days before the event, Dee went shopping, she was gone all day, when she came home later that night, she showed me all the decorations she had bought, as well the "naughty" things she had bought for the bachelorette party.
They had the suite for two nights, the night before, I helped her decorate the room, the plan was a bridal shower for friends and family from 11 to 2, then those partying that night could rest for a few hours, before a party bus picked them up at 6:30, they planned a fancy dinner, a night club, then later a strip club with a male revue, before coming back to the hotel at some late hour. Since she had the place for two nights, Dee and I spent the night fucking, the huge tub, and twice in the king size bed, and with her pressed against the large picture windows.
The shower went great, only Cheryl, Dee and Tracy knew the plans for the evening, so after the regular guests left, Tracy informed the rest of the bridesmaids and Melody what was planned for the night, they broke off for various rooms, Cheryl and Dee shared a room, Melody and Tracy shared a room, the other 4 girls had the other room. At 6:30, in their party dresses, they headed out for the evening, I saw the pictures, it was definitely two cougars and 5 party girls heading out for trouble.
During the evening, Dee sent me pics of the events, including Melody getting a lap dance from two male strippers, and a video of Melody being led behind a curtain by two more.
Around 3 am, 7 drunk women staggered back to the hotel room, there was even more alcohol for them to drink. At some point, they all started talking about sex, and sexual escapades. As each told her wildest, Dee said she found herself giggling, not a one could come close to hers, so far, the wildest, one young lady who admitted to a lesbian romp her college roommate. When it was Dee's turn, she relived those theater visits. The women all stared, in awe, and blushing as Dee shared the details.
Later, sharing the bed, Cheryl asked Dee what motivated her to do something like that, when Dee said she didn't know, Cheryl then started to ask more questions. Was she worried she'd get caught? Was she worried her husband couldn't stop them?, etc., etc.
The following weekend, out of the blue, Dee came into the living room wearing a short, revealing dress, and asked to go out. She looked stunning, who was I to deny. All through dinner, she would rub my leg with her foot, very flirtatious with every guy, a few times intentionally slipping her dress aside to flash me. No idea what made her so horny, but I didn't care. In the car, she grabbed my cock and demanded I let her suck it. The we saw the adult theater, with a twinkle and a grin, she said to stop.
Inside the theater, we leaned against the wall, Dee slightly behind me, my arm around her waist. I felt her dress move, she squirmed, then squirmed again, suddenly in my ear she moaned there was a hand between her legs. She then suddenly pointed out a row, and headed to sit down. As I sat down, she said No, wait, I moved back to the wall.
As I stepped back, two men rushed to sit beside her, of her own accord, she slid her top down before they sat. They quickly took the lead, each reaching for a breast to play with. Dee leaned her head back, let out a little squeal, and slid down in the seat. One of the men slid his hand up her skirt, as he did, she spread her legs as wide. I heard her cry out "Oh GOD", then her body shuddered as she orgasmed. I thought she was done, no, she let them continue. This went on a few more minutes, then she stood up, I thought she was done and moved towards her, instead she turned, pulled the dress up and removed it, clad only in her heels. She said something to one of the men, he got up and moved to the other row, she knelt on the chair, and spoke to the other man.
The man who went around pulled his cock out, and Dee quickly gobbled it up, the other man crouched down, and began to eat her pussy and ass. I was shocked, how far would she take this, I wanted to stop it, but, she made no indication she was done. A few times she backed off from the cock she was sucking and groaned loudly, then right back to sucking. Suddenly the man grasped her head and pulled it tight, his body froze, as he came in her mouth, like a good girl, she took it all, only letting a few drops drip, the man behind her brought her to another orgasm.
Dee dropped back into her seat, the man stood up, with a dejected look, she reached out and took hold of his pants, he quickly undid them and pulled out his cock, she aggressively began sucking him off. In no time, he too came, not all in her mouth, some on her breasts.
She stood and motioned for me, I handed her her dress, rather than put it on, she strolled out nude, several men took a feel as she did.
She slipped the dress on, told me I was next, she planned to fuck me all night. I was so hard, I could drive spikes, in the car, she turned in her seat and started to finger herself, by the time we got home, she came once, and was on the edge. In the garage, I helped her out, as she walked around the front of the car, I grabbed her arm, spun and bent her over the hood, yanking her dress down as I did, she shrieked as her breasts hit the cold metal, I dropped my pants and rammed into her. She let out a scream that probably woke the neighbors. I fucked her hard, she had a small orgasm and begged me to fill her up, at that point I stopped, stood her up, slapped her ass and told her to get in the house.
I took her on the kitchen table, just the right height, I slipped in her again, telling her to play with her breasts, as I rubbed her clit. This quickly brought her to a screaming orgasm, her legs clasped around me, she shook so hard I thought the table might break. As her body came down, I started fucking her again, when I was close, I pulled out and shot my load on stomach, the many arcs shot across her breasts and face too.
She slid off the table panting, dropping to her knees, she took my cock in her mouth to clean it, and suck me hard again. We headed for bed, we fucked once more, in the morning, we fucked again. When I told her to put some clothes on, we'd head out for brunch, she slipped on the same dress, no panties, no bra. At the restaurant, we sat beside each other, I could reach between her legs and finger her. She hardly ate, but kept whispering my ear she needed to fuck some more. While we waited for the valet to bring the car around, she told me to find someplace to park, she wanted to fuck me in the car. A few blocks down was a park, and true to her word, she climbed on my lap and rode me for all she could.
The next day, I asked what got into her, with a wicked smile, she said that talking about sex with those young women, realizing how boring their sex lives were, all week she'd been thinking about it, and all week it had been making her hornier and hornier.
Two months later, Cheryl called, they went out for drinks, girl time. Over drinks, she brought up what Dee had told her, she was intrigued, had never been any place like that, and was afraid to go alone, when Dee offered to go with her, she was still worried, Dee offered I could take her. Cheryl came over the next day, we discussed things, I showed her several videos. When she left, she was confused, a little afraid, a little excited, definitely unsure.
Dee and Cheryl are similar, 53, great physical shape, both natural 34D, both wear a size 6, but Dee is an inch taller, Dee is a natural strawberry blond, Cheryl a brunette, both fit the cougar definition fully, a few years back, the three of us spent a long weekend in Vegas, both women constantly getting hit on by younger men. Cheryl has been married/divorced, and admittedly, only been with one man, her ex-husband, in the 10 yrs since their divorce, she's been with no one else, just a lack of motivation.
Cheryl called me two days later, she had more questions, I laughed and told her she was overthinking this, I would be very happy to take her, I would not let anything happen to her, she could go as far as she was comfortable.
That Friday, Cheryl called, she was ready, she wanted to go that evening, she asked what to wear. I said a sweater with a loose neck, with or without a bra, and slacks (I knew there was no way she was prepared for a skirt). I said I'd pick her up at 6, when she came out to the car, I could smell alcohol, she said she'd had a glass of wine for courage. Once in the car, she took her coat off, she wore a cream, button down sweater, a regular bra, jeans and flats.
15 minutes later we were buying tickets, the clerk buzzed us in. At the top of the steps was the gay theater, we went around the corner to the two regular screens. When we arrived, there were maybe 10 cars in the parking lot, so I figured they weren't very busy, I was right. We walked into the first cinema, on the screen, a young brunette was being railed by two guys, Dee and I stood in the back, after a few minutes she asked what the other movie was. In this screen, two MILFs were in a 3-some with a hung stud. There were two guys sitting, 2 more leaning against the wall. After a few minutes, Cheryl took my hand and headed towards the seats.