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Coochie Coo Cougar Part 2: Trapped in her Tickle Jail m/f and f/m

wrestlingclown

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Apr 19, 2012
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As I posted last week, I started dating Sherry, a woman twice my age, and she fulfilled my fantasy of being tied down and tickled. http://www.ticklingforum.com/showthread.php?252958-Coochie-Coo-Cougar-f-m

Much to my discomfort, her beautiful large-breasted daughter overheard me getting tickled, and she expressed an interest in tickling me as well. For weeks I was at a loss over what to do. Jan had broken up with her boyfriend. She suggested a secret rendezvous that her mom would never know about--a situation that reminded me scenarios revealed on the Maury Povich show. She claimed she was simply curious and just 1 "tickle date" would satisfy her curiosity. I declined, remembering my promise to Sherry that I would never let another woman tie me down. But whenever Sherry wasn't around, Jan would attempt to seduce me. She would wear nothing but panties and a tight t-shirt with no bra, and she would tickle me until I had to lock myself in a room away from her, while suffering from an unsatisfying hard-on. Formerly, I would wait at Sherry's house for her to come home from work. I changed my pattern and made sure Sherry was there before I went to her house in order to avoid being alone with Jan because I knew the temptation would eventually be too much to resist.

One day, Sherry asked me why I now insisted on waiting until she was home before coming to her house. Reluctantly, I had to tell her than her daughter wanted to play the kinky game that she had almost caught us doing. Sherry looked ashamed. She sat down at the kitchen table in silence for a few minutes.

"Well, I'm not going to share you with her," she said stubbornly. "I'll fix her. I'm off this Saturday, and we will confront her together."

Saturday morning, I cut Sherry's grass and went inside to take a shower, all the while wondering how Jan would react. After I took my shower and got dressed, I found Sherry and Jan doing yoga exercises on the sunroom floor. Sherry wore black leotards, while Jan wore white shorts and a pink halter top.

"Hey Mark, who do you think is stronger--me or Jan?" Sherry asked.

"I think you are," I said.

"You know you are right," Sherry said, turning to her daughter, "let's wrestle."

"Mom, don't you..." Jan said, but Sherry suddenly attacked.

Sherry easily overpowered the much leaner Jan and pinned her to the floor.

"Mom, get off me."

"Tickle her," Sherry ordered.

"No!" Jan shrieked.

She squirmed in futility. I hesitated, surprised at Sherry's action.

"Tickle her," Sherry ordered again.

I advanced forward. Jan thrashed helplessly, her eyes pleading with me.

"Don't you dare," she said.

But I dared. I tickled her underarms and she laughed out loud, the reaction causing me to have an erection.

"So you want to play tickle with my boyfriend, huh?" Sherry asked.

"You told." Jan said, a betrayed look on her face.

"Keep tickling her Mark," Sherry said.

I did. I tickled her underarms again.

"Stop it. Stop it," Jan said between silly sounding giggles.

I moved over to her long pretty legs, held one, and tickled her foot. She shrieked and jerked so hard she almost toppled her heavier mother. I was surprised how strong Jan felt when she resisted. She tried to kick me with her other foot but couldn't manage the angle.

"Ooooh! I'm going to get you both," Jan said in frustration.

I tickled her other foot, and Jan laughed agian. I could smell her moist pussy. Despite the humiliating situation, she was getting excited. Her struggles ceased, and she went limp.

"Now, are you going to stay away from my boyfriend or do I have Mark keep tickling you until you agree he's off limits?"

"I'll stay away. He's a creepy little snitch anyway," she said, giving me a dirty look.

Sherry got off Jan. Jan stood, tried to slap me but missed, and stormed to her room, slamming her door.

********************

Several months passed, and Jan often condemned me as a snitch and a pervert, forgetting that she had attempted to instigate my favorite perversion. Meanwhile, she found another boyfriend--a guy who resembled me.

Sherry and I took a romantic vacation together, staying in an upscale hotel room. All day on the drive to our destination, Sherry wore a light blue button down blouse and a tight black dress, an outfit much like what a lady policeman would wear. That evening in the plush hotel room with a king-sized bed, she told me I was under arrest. She ordered me to strip, then she bonded me to the bed using the restraints she had purchased for our previous game of about 4 months before. This time she spread-eagled me much more tightly, so that I couldn't move at all. For some reason this alarmed me, yet despite my fear, my erection hardened. Sherry stood next to the bed, her hip leaning against the mattress.

"Do you want to know why you're under arrest?" Sherry asked.

"Why?"

"For not telling me right away about Jan's play for you."

"But I did tell you."

"Not soon enough. For that I'm going to put you in my tickle jail."

Sherry let her dress drop to the floor. She slipped her panties off, straddled me, and shoved my penis inside her pussy.

"There. Now you are in my coochie. My coochie is your tickle jail."

I started to buck.

"No. You are not allowed any friction. You must stay still."

She had me restrained so tightly it was hard to hump anyway. I complied.

Minutes passed, my penis stuck inside her coochie, while she stared at me as if she as a teacher administering punishment.

"Oh, I forgot to frisk you. Are yu carrying any dangerous weapons?"

"No," I said, realizing what she was going to do.

She started feeling me all over in a tickly manner. I struggled not to laugh, unable to even squirm away from her relentless fingers. Her fris search reached my arm pits, forcing me to laugh reflexively. She stopped her frisking but I burst out laughing again. There was an unbearable tickling in my penis.

"Get off," I managed to say. "It's tickling my dick like crazy. I can't stand it."

"I told you. My coochie is your tickle jail. My coochie alone is going to tickle you."

She sat with her arms folded, and she was right--just the thought that my penis was trapped inside her was making me feel so giddy, all I could do was giggle.

My body weakened. My belly hurt from laughing so hard. It was more torturous than the last time when she tickled me everywhere. I couldn't help myself. I started humping, and this alleviated the tickling feeling.

"I'm warning you. You'd better stop," she said.

I felt myself starting to cum, so I did stop, but the tickling feeling returned. To stop the feeling, I had to hump and before I knew it, I'd lost control, squirting semen inside my tickle jail. My penis softened.

"I warned you not to do that," Sherry said, and she started riding. Now, the opposite happened--the friction was tickling my penis and the only wa to stop it was to stop her from humping, something I could not do.

"Stop, ahaha, ha, ha, ha. Stop! Stop!" I yelled.

"You wanted to hump, huh" Well didn't you?"

"Please, I beg ahaha ha ha stop ayeayeaye..."

My penis became hard again, and she kept riding, the friction continued to tickle, and I giggled like an idiot. I lost all track of time, and can't remember when she took her blouse and bra off. I do remember her giving me breaks, kissing me tenderly, and telling me it was going to be all right...my jail sentence was going to be over soon. I think I faingted and she gently brought me back to conciousness.

She released me from jail and I immediately passed out again. I awoke in the middle of the night, free from bonds but a little frightened of Sherry's tickle jail. I heard her snore. I rolled over and went back to sleep. In the morning the sun was shining through the window. I lifted the cover and looked at Sherrys substantial backside. She rolled toward me and smiled.

"How does it feel to be a free man?" Sherry asked.

I overcame my fear of her tickle jail and let myself back in her coochie again.
 
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