One month later
Dawn, Jono, and I explored new ways and methods to expand our BDSM experiences. We found a local group of sexual explorers that met once a month to research and teach how to widen sexual pleasures and how to do them safely. The name of the group was “Tease and Torture.”
We attended our first meeting. The meetings are held at members’ homes. The lesson at this meeting was ‘Fisting.’ The moderator was a black-haired single woman. She was the perfect example of what a MILF would look like. An hourglass figure, perky breasts, and tight round ass. She was twenty-nine years old and introduced herself as Jean.
On the floor in front of the twenty-five, people at the meeting was a blow-up mattress. Jean asked for a woman to volunteer. Dawn jumped to her feet, stood, and excitedly volunteered to be the subject of the class. Jono looked amazed that she was so willing. She announced her name to the group.
Jean asked Dawn to remove her shorts and underwear and kneel on the mattress with her ass toward the spectators. Dawn had freshly shaved her pussy. She knelt on the bed with her bare round ass facing the spectators.
Jean then asked for a male volunteer with large hands.
John raised his hand; it was a sizeable working hand. He introduced himself as a long-time member of the group. He was a professional carpenter and used his hands daily on the job. His wife seemed very interested in the subject.
“Ok, John, you look like what we are looking for.” She handed him a large bottle of lube. “Now, take this and generously rub the lube around your hand and rub it on Dawn’s pussy.”
“Dawn, have you ever been fisted before?” Jean asked.
“No, my husband and our friend Harv are eager to see how it is done. I did have a pool ball in my cunt once.”
“John’s hand looks bigger than a pool ball. You don’t mind if John gets you ready, do you.” you are not ready yet, but you will be soon,” Jean replied.
“Not at all. My husband likes to watch me with other men.”
“Perfect, then, John. I want you to rub the lube on Dawn’s pussy and play with her clit for a few minutes.”
John rubbed the lube on his hands. Then knelt behind Dawn, separated her pussy lips, exposing her love hole, and began to massage her pussy and clit. All the men had a bulge poking against their pants.
As John continued to rub her pussy Dawn began to breathe heavily. Jason started rubbing her ass with one hand and tickling her clit with the other. Dawn’s pussy juice was mixing with the lube and Jason’s hand.
“I think she is ready, John. So now I want you to bring three of your fingers together and push them into Dawn’s honey hole. Just go slow until her pussy opens to receive all three.”
John started slowly poking his fingers against her opening and twisting them like screwdrivers.
“Good, that’s good. Have you ever fisted before, John?”
“No, but my wife wants to try it.”
John kept pushing and twisting his fingers, drilling her pussy. After about a minute, his fingers were in her pussy up to his knuckles.
“Great, John, now add another finger.”
John brought four fingers together and pushed and twisted until they were up to the knuckles.
“Are you ok, Dawn?” Jean asked
“Hell yes,” said Dawn in between breaths.
“Ok, John, add your thumb and some more lube.”
John did as told until four fingers and his thumb was inserted.
“John, remove your hand and let everyone see how her fuck hole has enlarged.”
Seeing how expanded Dawn’s pussy became made many of us horny.
“Ok, John, now the real test begins. I want you to lube up again, then lube Dawn. She looks wet and ready.”
John’s fingers and thumb slid easily into Dawn’s enlarged fuck hole. As he poured more lube over his knuckles, John started the same twisting motion.
“Doing ok, Dawn?” John asked.
“Fuck, you are spreading my cunt wider than it’s ever been. I am so horny right now. I love the pain and the pleasure I am feeling. Fuck me with that hand.”
Twisting and turning, his knuckles began to insert into her.
“Push harder, John. You are almost there. Dawn is a good subject.” Jean announced.
John pushed harder, twisting his knuckles harder and faster until his hand was in her up to his wrist.
“Shit, John, I can feel your whole hand in me; god, you opened me right up.”
“Do you want me to stop,” asked John?
“Do you want him to make you cum, Dawn?”
“Damn, yes. I am so hot right now.”
John would take his hand out to see how wide her pussy had opened. Then shoved his hand back in above his wrist. Dawn’s breathing became sporadic as he fucked her with his arm.
“I am going to cum. I think I am going to squirt.”
Dawn’s juices shot from her, wetting the mattress and John. John pulled his hand out to let Dawn calm down.
“Ok, I hope you have enjoyed our session. If anyone has any questions, I will answer them during our break. There are refreshments in the next room,” Jean announced.
During the break, Harv asked Jean to have dinner with him. She said she would be glad to. They set up a time on Friday at five pm.
That Friday
I picked Jean up at her home, then went to a lovely steak house for dinner. She looked great. Everything about her was sexy. Her dress flowed nicely over her body, showing off her womanly assets. Her black hair curled around her face and was cut above her eyes.
I hoped she would be willing to have sex on the first date.
We talked about Dawn and Jono and some of our adventures at dinner. We also talked about the group and what they had planned. I volunteered to have everyone who belonged to the group over to my house for a meeting.
After dinner, I drove Jean to her house, and she invited me for a cocktail.
“Harv, you can pour the drinks. I am going to change into something more comfortable.”
I poured the wine and then sat on the couch, waiting for her to return. When I saw her walk into the room, I stood to greet her.
She wore a black nightie with pink trim around the top of the breast line and the bottom, which fell just below her black panties with pink trim.
“You look wonderful,” I said as I reached over, grabbing her by the waist and pulling her into me so she could feel my rising shaft.
“Wow! I guess you will like it. Now the only question is, how long will I be wearing it?”
We kissed with a rising passion building in our bodies. Jean placed her arms over my shoulders and rubbed my head. Out tongues entangled our hands roaming. My hands went to her breast; her hands went into my pants. We parted lips to remove her nightie. Her tits were amazing, she had breast implants that gave her a thirty-four-inch chest, and her nipples sat on top of perfectly round areolas.
I placed my mouth on one of her nipples, flicking it with my tongue and sucking on it.
“Mmmm, feels nice.”
Jean fell to her knees, unhooked my belt, pulled my pants and underwear down, and took my cock into her mouth. Jean swallowed my cock; I could feel it in her throat. After a few seconds, she came up for air, leaving her saliva dripping from my cock. Down she went a second time, only this time she grabbed my balls and jerked my cock when she came up for air.
After about six times of swallowing my cock, I pulled her up, and we kissed. I pulled her tight into me.
“What the fuck? Do you have a vibrator In your pants?” I exclaimed.
“I thought you knew; the club knows; I assumed they mentioned it. I am a shemale. If you want, I will leave. I am sorry.”
“Please do not be sorry; I have often thought about reaching into a woman’s pants and discovering a hard cock. It just caught me by surprise, that’s all. You are pretty and sexy. Let’s head down to my playroom.” I grabbed her hand and led her to the room.
“This is awesome; we could have some great meetings here.”
“Let’s discuss this later; I have unfinished business with you!”
I reached over and pulled her into me so our cocks would rub against each other. I kissed her very passionately.
As we kissed, her hands grabbed both cocks and rubbed them together. I dropped my hands to her ass. Her ass cheeks were soft and round; gliding my hands across her ass, I would stop and pinch her ass cheeks, and she would squirm a little. I reached down further until I could touch her balls. She had a nice nut sack that hung a couple of inches before forming around the balls. Moving my hand back to her ass, I slid in a finger and searched for her prostate gland. I ran my finger over it, just barely able to reach it from the standing position.
“Oooh, you know how to make a girl hot.”
It was my turn to get on my knees. I wanted to feel her cock in my mouth. Using my tongue, I licked her cock head and pressed my tongue against the vein that ran along the underside. She moaned loudly and grabbed my head, pushing my mouth down her shaft and to her balls—my throat accepted her length and width. I have a high gag reflex.
“My turn, lay on the bed, Harv, on your back.” Jean panted.
Jean straddled her body over mine and moved her cock back to my face. I grabbed her seven-inch cock and swallowed it. I reached up to massage her breast and see how sensitive her nipples were.
Jean bent down, aimed my cock into the air, then swallowed it. We fucked each other’s mouths.
“Jean, I love how you handle that cock; I am so horny.”
“Harv, let’s move to the edge of the bed and put your ass right at the edge.”
She got on her knees, which gave her access to my ass and balls. She placed one of my balls into her mouth.
She poured some lube on her cock and my ass. She stuck a finger in my ass; she knew right where my prostate gland was and pushed against it.
“Fuck, stick two fingers in that hole,” I told her.
She expanded my hole to accept her cock, playing with my ass hole a few seconds more, and she stood up. Using my legs as an anchor point, Jean pushed the head of her cock against my ass hole and then slid it into me.
I watched as her cock entered and exited my ass hole. She grabbed my cock and began jerking it while she fucked me.
“Oh shit Jean, don’t jerk my cock. I will cum too soon. I love the way your tits bounce as you fuck me.”
“Do you want me to cum in your ass,” asked Jean?
“Yes, fill my ass; I want to watch you cum. I am getting ready to cum. You are hitting everything just right. I will cum without touching my dick; that is how good you are fucking me.”
I watched as her cock left my ass. She pushed it down and rammed it back into my ass. She grabbed my legs with a firm grip. Her balls were up to my ass, her body stiffened, and her head moved back as she let out a very loud moan. She shot her load into me. My balls tightened my cock began to jerk on its own. One shot of cum on my chest, one on my stomach, one drooling down my shaft, the last cum making a ball at the top of my cock. Jean bent over, licked it off, then lapped my cum on my body. I could feel her cum running out of my ass.
“Awesome, Jean, that was awesome. Lay here next to me and kiss me. I hope this is not the last time.”
“I hope not too. I had fun tonight and enjoyed your company,” said Jean.
“Would you consider getting together with Jono and Dawn? I won’t tell them you have a cock; we can surprise them with that.”
“You don’t mind I have a cock instead of a pussy?”
“Not at all. If you can spend the night, I would like to kiss that ass of yours and fuck your man pussy.”
The Next Friday
I called Jean to ask her if she would join Jono, Dawn, and me for some sexual fun. She said she would love to.
My next call was to Jono.
“Hello, this is Harv. My girlfriend and I want you to join us for sexual fun tonight. Can you make it?”
“That would be great, especially since Lenny is home for a few days. Why don’t you come over here.” Lenny is their son.
Jean showed up at the house around six. She was wearing a black leather top just below her thighs, hiding her leather G-string. We hugged and kissed. I was eager to see Dawn and Jono’s faces when her G-string would be removed.
We walked over to Jono’s and Dawn’s. The door was unlocked, so we walked into the foyer. We noticed a pair of Dawn’s underwear lying on the floor. Further down the hall, we discovered her bra. We walked down the stairs to the playroom.
Lenny was lying on the bed with his mother’s mouth wrapped around his cock. Jono was about to fuck Dawn from behind.
“Hey Lenny, your mother sure is fucking hot. I can’t wait to fuck her. I want you to meet Jean; we met her two weeks ago. She has a surprise for everyone.”
“What is the surprise?” asked Jono.
“Jean, why not go over and make out with Jono.”
Jono walked over and gave her an intense tongue kiss. Jean wasted no time and grabbed Jono by the balls, fell on her knees, and swallowed his cock.
“Shit, Jean, you are fucking horny, getting right to it. Fuck swallow my cock again.”
Dawn was swallowing her son’s cock. Lenny told his mother what a great cock sucker she was and how much he wanted her.
Jean pulled away and asked Dawn if she would mind being tied up. Lenny thought that it would be a great idea. Dawn was eager to be the center of attention.
“Dawn, lay on the punishing bench!” commanded Jean.
Dawn knelt on the rear section while Jean tied her legs to the kneeler bars. Jean went in the front and buckled Dawn’s arms and hands to the resting bars. In the center was a higher belly stand that kept her ass in the air.
Jean grabbed a ball gag to place in her mouth. “Now, if what we attempt hurts, just moan loudly and shake your head. Understand?”
Dawn shook her head yes.
“Ok, Lenny, I want you to fist your mother’s pussy.”
Lenny grabbed the lube and rubbed his hands while Jean got Dawn’s pussy ready. Jean rubbed Dawn’s clit and stroked her pussy. Dawn was moaning with pleasure. Dawn’s pussy released her natural juices. Jean gave Lenny instructions concerning fisting his mother. Lenny inserted his hand and arm just above his wrist.
“How is that, mom?”
“Mmmm,” while shaking her head yes.
Jean grabbed a leather paddle and slapped it across Dawn’s ass.
“Now, Jono, come over here and put your hand into your wife’s ass.”
Lenny was fucking his mother with his hand as Jean was getting her ass hole ready. Jono placed some lube on his hand. Separating her ass cheeks, Jono pushed three fingers into her. As Dawn moaned, he pushed in four fingers and his thumb. He squirted some more lube onto her ass and inserted his hand into his wrist.
Dawn was shaking her head no and moaning loudly.
“Do you want Jono to stop?” asked Jean.
Dawn continued to moan, only now shaking her head no again.
Jono repeated the process, fisting Dawn’s ass.
“Harv, play with Dawn’s tits.”
I walked over, fondled Dawn’s breasts, and pulled on her nipples.
Jono fucked his wife’s ass while his son fisted his mother’s cunt.
Jean walked to the front of the bench; Jean pulled down her panties, revealing a hard dancing cock in front of Dawn’s face.
Lenny and Jono looked in amazement as before them was a pair of nice tits on her chest and a hard cock below her waist.
“I want some of that,” Lenny cried.
“In a minute,” Jean replied. “Right now, I want your mother to suck my cock.”
Jean removed the ball gag, grabbed Dawn by the hair, and inserted her cock into Dawn’s mouth.
Jean fucked Dawn’s mouth. Lenny removed his hands and shoved his cock into his mother’s pussy. Jono kept fucking her ass; he could feel Lenny’s cock through the thin separation between ass and pussy.
I got behind Jean, got the lube, wet down my cock, and was able to insert it into Jean’s ass. I held on to her tits as I pumper her. Jean began to groan, Lenny was breathing hard, and Jono’s cock began to bounce.
“Fuck, this is so damn hot,” I blurted out.
I shot my load into Jean’s ass. Lenny released his sperm into his mother. Jono’s cock began to shoot cum all over Dawn and the floor. Jean pushed her cock into Dawn’s mouth one last time and came in her mouth.
“Wow,” that was amazing. I learn more every time I come home. I am staying longer. This is going to be one hot summer,” Lenny said.
Jean, we are not done with you yet. Welcome to the group.
