Heather's Art Club

My latest fantasy involved older women. I loved the idea of kinky sex, but was never able to find those kind of relationships. I thought that maybe an experienced older woman would be able to teach me some things. I was happy to be her boy toy.

I went on Tinder to see who I could find. I matched with a few, but they seemed to be looking for longer term relationships. Then I crossed paths with Heather. She was twenty years older than me and still looked great. Her profile says, "Only looking for friends." so I thought it I'd give it a try.

We chatted a bit and I started to explain my situation. "To be honest, I'm hoping to find someone older than me to take control and help me explore the world of kink."

"Oh, I love kinky sex! I think I have some things I can teach you..." she replied.

The next night we went out for drinks and had a great time. The subject of kink didn't come up, but she asked if I wanted to come back to her house and go swimming.

"Of course, that sounds great!" I said.

I followed her to the house and it was huge. When we got inside I looked out of the sliding doors and saw blue lights reflecting off of a very nice pool.

We walked onto the patio and she immediately started stripping down. She turned around, looked at me, and rubbed her tits. Then dove right into the pool. After coming up for air she asked "Coming in?"

I was nervous but I stripped down and jumped in with her. She swam up to me and we started to hug and kiss. As we made out I felt her hand grab my cock. I responded by touching her pussy. She then asked, "Ever been sucked off in a pool." I hadn't, and my cock grew hard as I told her.

She took her hand and patted the edge of the pool. "Hop up. It's time for lesson one." I jumped up and sat with my legs in the pool and my cock pointing straight up. I watched her take it into her mouth and give me the best blowjob of my life. She didn't stop until I blew my load, grunting as she swallowed every drop.

Over the next few weeks I would come over and we would have kinky sex. She tied me up and spanked me. We had sex in public. We did some roleplay. She told me about how much she loved big cock. And when I curiously asked what was the biggest cock she ever had, she pulled out her phone and showed me. "This is my friend Jason."

I looked at the picture and it was one of the biggest cocks I've ever seen. It must have been 10 inches. "Holy shit, that is massive."

She laughed and said, "Why do you think we have stayed friends?"

One night as we were hanging out, she mentioned that she had an upcoming art club with five other women. The ladies would get together and have wines, cheeses, and draw together. "Would you be willing to help me out with the event?" she asked.

"Of course." I said. "Whatever you need."

The day of the event, she asked me to dress nice and to arrive about an hour earlier than everyone else. When I got there she seemed thrilled to see me. "Thank you so much, I could never have done this without you!"

She brought me inside and got me a drink. She explained that as they are drawing, she wanted me to go around and take orders and serve drinks. I'm shy, but seemed like something I could handle.

Then she looked at me and said, "Pinky swear that you will do everything I ask tonight, no matter what. Otherwise the night might be ruined." I wasn't exactly sure what I was agreeing to, but our pinkies wrapped together. She smiled.

I finished my drink and she quickly poured me another. "Hold this, and let's go get you ready."

"Get me ready?" I asked. I was so confused. She grabbed my hand and led me into a spare bedroom. I was absolutely shocked with what I saw...

On the bed was a tiny black and white French maid outfit, white thigh highs, white gloves, a black choker, a long brown wig, and a silicone body suit with fake tits. My face turned bright red as I asked, "Are you serious?!"

"Absolutely," she responded. "you pinky swore". It was true, I did... She explained that this isn't a normal art club, and there was no need to be embarrassed.

"You promised to help, and you said you were curious about dressing up, didn't you?"

Another true statement... I was scared shitless, but also turned on. What the fuck had I gotten myself into?!

"I have to get a few things ready, but go ahead and get dressed." She then left the room and closed the door. I took a deep breath and looked at the outfit. This was fucking crazy. But I went ahead and took off my clothes. I put on the black panties. I slipped on the fake tits and choker. I put on the black and white outfit. Then the white thigh highs, wig, and finally the gloves. I looked like such a slut. The outfit barely reached my cock and panties.

As I nervously looked in the mirror I heard the doorbell ring. Oh shit....the first guest has arrived. I looked at the window and considered jumping out. And then more guests arrived over the next 10 minutes. I put my ear against the door and listened to the sounds of women chatting. I was terrified.

After 15 minutes or so Heather walked into the room and closed the door. She smiled as she saw me dressed up. "This is perfect! Look at your big tits! Thank you so much!" Then she walked up and kissed me and gently rubbed my panties.

"Ok this will have to wait. My guests are here, it's time for you to take orders." I turned red. "It's gonna be ok, I'll be there with you the whole time." She then handed me a pad and pen.

We walked out of the room, and I had to fight every instinct to run. My legs felt like jelly, so I probably wouldn't have gotten far anyway. I was scared and I instinctively grabbed her hand.

And then we walked through the door holding hands. A group of older women were sitting in a circle at small desks with art supplies. Heather left out one little detail about the night... They were all surrounding a good looking guy in tight white underwear, and drawing him.

The talking immediately stopped and everyone in the room looked up at me. I turned deep red in the silence. I stood there with my cock barely covered, and fake tits filling out my uniform. I tried to hide myself with my white gloves. After a moment, the ladies started gently clapping and smiling.

As the clapping stopped, Heather said, "Ladies, this is Becky. She will be taking your orders and serving you tonight. And Becky, in the middle of our circle you will see my friend Jason. He is our subject tonight, so please take care of him as well."

She then left my side and went to her desk to draw. Thankfully the rest of the ladies also went back to drawing while I stood there humiliated. And now it was time for me to take orders.

I slowly approached the first woman, my voice shaking as I said, "Hi...maam, what can I get for you."

She responded, "Oh you look so cute with your costume." lifting up the dress to look. She then adjusted my costume and gave me her order.

I went through the rest of the women fairly quickly. When I approached the last one, she started rubbing my thigh as she gave me her order. My cock fell out of my panties but surprisingly no one laughed as I tried to tuck it back in.

The final order was Jason. "Hi Jason, what can I get for you?" I asked as I looked back and forth between his eyes and his underwear. I could see the outline of his cock so it was hard to look away.

"A beer is fine." he responded while smiling.

I walked out as quick as possible and into the kitchen trying to catch my breath. I sat down and pulled myself together. And then began to make drinks. As I went back in to serve everyone I started to feel a little more comfortable in my outfit. Heather then asked me to serve a cheese platter. I came back and smiled as I held out the tray to the guests.

I continued to serve everyone as needed and watched them draw Jason. His cock was covered, but I kept thinking back to the picture she showed me. I knew he was hiding 10 inches. They finished up and I got them a new drink as they compared drawings. Heather whispered something to Jason, and he got up and left the room.

A few minutes later as I awkwardly stood there in my uniform, Heather announced, "Ladies, it's time for our second drawing." I wondered what it was as they went back to their desks.

Heather left the room for a moment, and came back in with a chair and a pillow. She placed them both in the middle of the circle. She then left again, and came back with Jason. This time he was completely naked and his huge cock was hanging down. My eyes opened wide and the ladies applauded as she walked him to the circle. "Have a seat Jason."

Then I heard, "Becky, please approach the circle." I had no idea what was going on and slowly walked closer with all eyes on me. "Please enter the circle and kneel on the pillow." I could see where this was going and again had the urge to run as fast as I could. But I kept looking at the huge cock, and slowly took my place on the pillow.

I sat there for a moment and nothing happened. No one said a word. Why weren't they drawing? The all just stared at me, and this continued for about a minute. I asked, "Is this ok?"

No one responded.

I got really nervous, and looked at his cock. I just wanted to break the tension and had no idea what to do. So my hand reached out and grabbed it. Still nothing. but I think I know what they are waiting for now.

I leaned in and kissed the head. The ladies began to clap which turned me on. And his cock started to grow. But the ladies still weren't drawing. Then my urges took control. I put the head of his cock into my mouth. It barely fit. And as I drooled onto it, my hand wrapped around the cock and started to jerk while I sucked on the head.

The ladies began to clap again. Then the sound of claps was replaced with the sounds of pencils and my mouth.

I had tunnel vision and couldn't see anything else in the room but that cock. I kept jerking and sucking, amazed at how big it was. I moaned loudly the whole time as the ladies watched on.

He didn't say a word, and before I knew it, his cock was pulsing in my mouth. I kept it there as cum spilled out onto the floor.

My hand didn't stop jerking as I pulled my mouth away. I couldn't believe what I just did. I started looking around at the ladies with cum dripping off my face.

There was a long pause before another long round of clapping.

"Good job Jason, you are excused." said Heather.

He left the room and I sat in the circle looking like a cum covered slut. "Ladies, I think Becky has done a great job, and it's time to give her our thanks." The ladies all agreed.

I was then escorted into the kitchen with all six ladies. "Becky, please lie on the table." I lied down on the kitchen table as they surrounded me and looked down. All dressed up with cum on my face looking back up at them.

Then I watched as the ladies took turns jerking me off. No talking, laughing, or smiling. It was almost like a sexual ritual. They looked like stern teachers on a mission. As I was jerked, the others would touch my balls, rub my legs, and massage the rest of my body. It was quiet other than the sounds of a wet cock, shifting fabric, and the tiny noises I was making.

When I couldn't take it anymore, I said, "Ladies, I'm about to cum!" They continued with the serious expressions, but I felt the jerking get harder and faster. The hands on my thighs pressed tighter. My balls were squeezed. And then we all watched the cum explode out of my cock. Every drop landing on my apron.

The ladies looked at each other, and watched as Heather dipped a finger in my cum and put it in her mouth. The rest of the women followed one at a time until each got a taste. This truly was a different kind of art club!

After they finished, they sat me down in a chair. Then the ladies came over with their drawings. Each one smiled as they handed me a beautiful drawing of a French maid sucking cock.

They thanked their host for a great evening and went home for the night. I spent the next few hours in my maid outfit helping Heather clean. When I was done she showed me a group chat between the ladies.

"Becky was so great, I loved her cock!"

"I can't believe Jason came in her mouth!"

"That outfit was unbelievable. Her cock was basically out all night!"

"Heather, please bring Becky next time!"

I couldn't wipe the grin off my face. I went home with my artwork and hung them around my office. I looked at them every day and eagerly awaited the next meeting of the art club.