Dinner with Estelle by Brian Houlihan

Dinner with Estelle

Copyright @2000 by Brian Houlihan

All Rights Reserved

bhoull@ameritech.net

We met at the pool. I was staying at this luxury hotel in Montreal, the Parc. An old buddy of mine, Pete, had somehow talked some movie studio bigwig into giving us a nice hunk of money to go and write a script for a movie idea he had pitched. I didn't believe it when he phoned me in Chicago and told me the deal he had lined up. However when the paid for, round trip plane tickets to Montreal arrived in the mail, I started believing.

The whole thing was such a lark that I just kind of slept walked through it. And I'm sure that helped the comic aspect of the script we were working on. I knew Pete from our stand up days in Los Angeles and had moved back to Chicago about four years now. But we still kept in touch, talked on the phone about once a week. We were still both struggling with bread and butter jobs to make the rent. I was trying to get a play of mine produced in Chicago and Pete was still doing stand up.

Then he phones me with this great deal. He had a fat budget and gave us a month of working together in Montreal. Pete said he had talked me up as a playwright from New York and they quickly agreed to me working on the project with him.

Anyway Pete and I would meet in his hotel suite five days a week and hash out ideas for the script, from 9 til 1 pm. That was our day. Pete felt that the morning hours were the best for fresh, awake ideas. Basically we could fuck off the rest of the day.

So I took to going to the pool in the afternoons, from about 2 to 2.30 pm until I got bored. It was the middle of June so the situation for girl watching was ideal. However after about three days I had the best looking women pretty much checked out. And most of them were with guys, unfortunately. But the girl watching was nice. Sometimes I would smoke a joint in my room and then hit a chaise lounge by the pool and just let my eyes and mind wander. It was fun. But not the real thing, of course.

Just fantasy.

That changed the next Saturday afternoon. Since I didn't work on the weekends (Pete believed in lots of R&R. Heh. Heh.) I hit the pool earlier on Saturday. Around noon. There seemed to be less traffic than ever. I figured most of the weekday people were business types and went home on the weekend.

I was just sitting down on my chaise and putting on suntan lotion, when I saw her. A tall, regal woman with jet black hair, dark features, very long legs and big tits, had just stopped at a chaise directly opposite me across the pool. She was wearing a black two piece suit that just seemed to accentuate her great figure and powerful breasts. I attempted to be very nonchalant and take only very cursory glances at her.

She was wearing dark sun glasses so I really couldn't see if she was looking at me. Her skin was sort of olive toned and I wondered if she was Latin. She just seemed to ooze sex. My dick got hard looking at her.

Her intense sexuality got me fantasizing immediately. I would go out of my way to shift around on the chaise and glance over at her.

After about twenty minutes she jumped into the pool and swam around a bit. Then got out and lay down. She looked over at me and we exchanged smiles. She looked better than ever wet. After a while I feigned sleep and would peek over at her. Get this: she would touch her tits or stroke her hand over her stomach now and then and look at me. It was weird. Could she tell I had a hard on? Probably.

Well I was too chicken shit to make any kind of move that Saturday. But I did jack off that night fantasizing about her. The next day I was so keyed up about seeing her at the pool again that I seemed very nervous and anxious. I smoked a joint and had two drinks before going down to the pool at 11.30 am. I was very, very horny at this point and kept telling myself, 'You have to make a move on her. Today!'

She wasn't there when I arrived at the pool, so I got my chaise, lotioned myself, and pretended to be solely interested in getting a suntan.

I kept telling myself not to be intimidated by her beauty. But I was.

"Good morning!" I looked up. It was her!

"Well good morning Beautiful. I was praying you'd show up." She was giggling. Good.

"Me too. For you. Do you mind if I join you?"

"My pleasure." I gestured at the empty chaise lounge next to me. I couldn't believe this good fortune. Had she thought about me?

She dropped her bag on the chaise, stepped out of her sandals and bent over to get something out of the bag. Her ass was to die for.

Her skin tight turquoise suit hugged every pore of her magnificent ass. She got a container of suntan lotion and began applying it while standing up.

"Oh, forgive me. I am Estelle." She extended her beautiful, oily hand. Long fingers with nails painted dark purple.

"Sean." A firm grip.

"Nice to meet you Sean. Are you Irish?"

"Yes."

"Oooh I thought so. I am very attracted to Irish men."

"Lucky me. And I am attracted to Latin women. It's kismet!" She was giggling again. I liked making her laugh. She seemed more vulnerable, available.

We made small talk while we sun bathed. I told her about the movie project and she seemed very impressed.

"I love artists."

"Good." Then she told me she was there because her husband was there for some kind of computer programming conference.

"Aw. I'm sorry to hear that Estelle. I was hoping you were single." Here she put her hand on my thigh.

"Oh I am! Do not worry about my husband. I have lots of boyfriends. He prefers that."

"Really?" Another squeeze on my leg.

"Really Sean. Why don't you come to dinner tonight? And I will show you."

"Thank you. I will."

The rest of the afternoon passed in a happy fog. She asked me if I would like a drink? Sure. She ordered us a pitcher of Magaritas. I was getting buzzed and fantasizing about her and this mysterious dinner coming up. How open was their marriage? I noted her touching herself much more today and looking at me and smiling. At one point I purposely touched my dick and smiled back. She giggled. My prick was rock hard in my bathing suit. She was glancing at it a lot.

I was getting a bit burnt so after a few hours begged off to take a nap before our dinner date at her room. I was gathering my stuff up and about to leave.

"Oh, Sean!"

"Yes?" I walked back over to her. She smiled up at me. Then reached out and took hold of my hard dick in my suit. I was paralyzed.

"Is this for me?" I was speechless.

She was giggling again. She let go of my overheated dick.

"See you later Sexy."

Well you can imagine how turned on I was now. I had to really restrain myself from jacking off before the dinner date.

I took a fitful wet dream nap fantasizing about her. I was hard all the time now. And dripping.

At the appointed hour, I arrived at her hotel room door. I was really curious as to what her husband would be like. If nothing else, I would get to look at her through dinner at least. I was dressed casually in nice slacks and a shirt. I had also done a few more hits off a joint, so I was good and buzzed now.

I knocked at the door.

"Is that you Sean?" Her voice sounded kind of far away.

"Yes."

"Come in honey. The door's open."

This was weird. I opened the door. There was a little hallway. No sign of Estelle.

"In here, Sean. In the living room." I walked into the next big room. The room was a suite and quite nice.

Estelle appeared to be in her nightclothes. Doing some kind of squats on the floor.

"Aren't you going to kiss me?" I walked over to her and noted that she was in an almost see through nightgown. It was black but you could easily make out the big extended nipples of her large tits and even some pussy hair. She pulled me to her and kissed me on the mouth.

"Where's your husband?"

"He's right here!"

Good God! I looked down and realized that she was literally sitting on some guy's face. She had an evil smile on her face.

"Gerri's getting a treat. Because he's been a good boy." I just stood there. I could not believe this. His face disappeared under her ample ass cheeks.

"Lucky Gerri."

"I think so. Do you like to be smothered Sean?"

"Uh..yeah." Giggling again.

"Good hon. Maybe we'll do that. Gerri loves to smell my asshole. Now go have a seat and Gerri will bring us some drinks before dinner."

In a trance, I found a cushiony chair and sat in it. Estelle was smiling at me as if this was the most normal thing in the world. For her to invite a strange man to dinner and greet him sitting on her husband's face, wearing next to nothing.

She slowly got up from his face, then leaned down and swatted his dick. Hard. Gerri groaned and curled up in pain. Estelle looked at me with mischievous eyes.

"Bring us some drinks faggot." Then she casually and confidently walked over to the couch and plopped down on it.

"Do you like my outfit?"

"I love it."

"I thought you would. Do you like hairy pussy or shaved?" That threw me. More giggling.

"Am I embarrassing you Sean?"

"No. No. Just not used to it, I guess. Are you trying to embarrass me?"

"Maybe a little. Teasing. You seemed so straight laced at the pool. But horny."

"Well you read that right."

"Heh. Heh."

Then her husband came out of the other room with drinks on a tray. He was a slight man of about fifty, with a receding hairline. His hair was blondish, what there was of it. Very femmy. He seemed nervous. Afraid to make a wrong move in front of his wife or boss or whatever she was.

As I adjusted my eyes I noted that Gerri was wearing ladies' culottes and a woman's white blouse with tiny flowers on it. He wore low heeled shoes. It was all so weird.

Gerri handed me a drink and then put one in Estelle's hand and the other on the end table.

"Sean, this is my husband, Gerri."

"Nice to meet you."

"Nice meeting you, Sean."

"Right here, Precious."

She was patting the seat on the couch next to her. Gerri obediently sat down.

"Gerri, tell Sean you don't mind if he fucks me." Lots of giggling. Gerri blushing.

"I..I don't mind Sean. Really. Whatever Mommy wants."

I could not believe how weird this was. Obviously Estelle loved embarrassing Gerri. I gulped my drink.

She was playing with Gerri's hair and looking at me. Smiling evilly.

"See Sean, my husband Gerri is a big sissy. He knows that he could never satisfy me with his tiny wee wee. He understands my needs and that I need real dick from a real man. Right honey?" Gerri nodded like a scared wind up doll.

"Actually Sean, we have a great relationship. And I get all the dick I want. Heh Heh. And Gerri is always respectful to me. As a matter of fact, he is such a sissy that he actually enjoys sucking another man's cum out of my pussy. After I've been fucked by a real man. With a real dick. Right Sweetie?"

"Ow!"

"Shhh." She was pulling his hair hard now and then. Yanking it to hurt him. No wonder he was on edge. She kept looking at me while talking to him.

"We have a very special relationship. Don't we Gerri?"

"Yes Mommy."

"See. He loves seeing me as a maternal mother figure. One who is both nurturing - but who is also capable of punishing him for his naughty behavior." Here she looked at me, then hauled back and slapped him very hard in the face. Then backhanded him. I could see handprints on his pale face.

"See. He needs that. Because Gerri knows that punishment comes from love and understanding. Don't you, Cupcake?" Yanking his hair.

"Yes M..mommy."

"And that's what sissies need. Hard spankings. Whippings. Then they have a good cry in Mommy's arms. And they become more obedient. Better servants. Right, Honeybun?" Gerri was looking embarrassed.

She yanked his hair, then a really vicious slap in the face. Now he was crying, holding his cheek.

"Answer me, faggot!"

"Yes. I'm sorry Mommy."

"You're going to be a lot sorrier if you don't settle down Missy. Do you want me to whip you right now, in front of Mr. Chambers?"

"No Mommy. Please, no."

"You are supposed to make me proud in front of our guests. Instead you are embarrassing me. Get undressed faggot!"

Gerri stood up nervously and quickly took off all his clothing. I noted him wearing panties just before he took them off. No body hair. Small dick and balls.

"Freshen our drinks, Sissy."

"Yes Maam."

Gerri gathered up our drinks and quickly exited into the kitchen. My head was swimming. Estelle had that devilish smile again.

"I hope this isn't making you uncomfortable, Sean."

"Oh, no. Not at all. As a matter of fact, it's given me a hard on." Her eyes lit up at this remark.

"Excellent! Come sit over here. I knew you were going to be fun." My dick was poking a hole in my pants. I didn't care.

I sat down next to her and she smiled at me. Her tits were right in my face. And if I glanced down I could see her cunt hair. As soon as I sat down, she began rubbing my leg.

"I like you hard around me Sean. That's flattering to me."

"Oh I bet you get flattered a lot." Convulsive giggling. Then her hand on my neck. Shivers of excitement.

Sexy perfume. Then she was kissing me. Squeezing my hard on through my pants. Her tongue easing into my mouth. Liquid sex. She broke the kiss. Out of the corner of my eye, I saw Gerri standing there naked with our drinks.

"Mm hm. We are going to get along just fine. Oh, here's our tiny dicked sissy."

"Is he alright with this?"

"Are you kidding? He loves this. It turns him on. Gerri, come here." He quickly scooted in front of her. He had a hard on!

She grabbed his dick and kind of displayed it to me.

"See. His tiny wee wee is all stiff. Just like the big mens. Huh, baby?"

"Yes Mommy."

"You better answer me right away faggot. Or I am going to beat the shit out of you. Do you understand me Miss Tiny Dick?" For emphasis, she slapped him in the balls very hard.

"Ow!" Gerri doubled over in pain.

"That's just a taste Gerri. Don't tempt me. You know I love beating you. Sean, it's true. I can cum just from whipping her. It's wonderful. Sometimes I spank her hard over my lap and when it's over I realize I came about twelve times. Cum all over my legs and the chair. Ha. Ha."

She was so sexy. And scary.

"Gerri, Sean tells me that my playing with you has given him an erection. How do you feel about that?" He was still slightly bent over from the slap to his nuts.

"Whatever makes you happy Mommy. That's what I want."

"I want him hard all the time. Do you understand me?"

"Yes Mommy." Now my dick was harder than ever. Was she telling him to touch me? "Good girl. Now why don't you show our guest some respect?"

"Yes Mommy." Gerri stood in front of me, then knelt down. Then he parted my legs with his femmy hand and then moved his head down to kiss the tip of my prick through my pants. It felt good.

"Ooh that feels good Estelle." She reached out and held Gerri's head there over my prick.

"Stay. Don't move. Good. Good dog." This was such a turn on. And whenever she hit him her tits bounced and swayed a lot. Now she was playing with Gerri's hair while he kept his mouth over my dick.

"Gerri, tell Mr. Chambers how you could help him relax. If he wished." Gerri lifted his head up and looked me in the eyes. As if programmed.

"Mommy says I am an excellent cocksucker. I would really love to suck your cock Sean." He was actually pleading for it. A chill ran through me. I was feeling wild.

"Gerri I would love you to suck my prick for me. Take my clothes off for me and start suckin' my dick faggot."

He went right to work. Estelle was beaming with pride. Gerri removed my loafers, socks, then pants, underpants, then my shirt. Estelle was rubbing my ass with her hand and kissing me on the mouth.

I had lifted my ass for him to remove my pants and underpants. Now that I was naked I sat back down again. Gerri's hands were shaking hard. He was obviously very, very turned on.

"That's what you want isn't it, Sissy?" Estelle said.

"Yes Mommy." As his warm mouth opened and engulfed my inflamed dick. Oh god he felt good. His femmy hands caressed my hot balls as he slowly worked up and down on my shaft.

"Oh that is so fuckin good babe! Suck that dick honey." Now I was playing with his hair.

Estelle kissing me again. Her tongue taking control.

"I'm..I'm...AGHHHHHHHH!!! oooh fuuuuckkkk." Suddenly my prick was shooting off like a wild out of control fire hose. I bucked and pumped unconsciously. Gerri stayed with me all the way, riding my prick down and swallowing as much of my cream as he could. It was heavenly. I had been so keyed up. Came much much quicker than I wanted to. It went on for a long time. I kept moaning and screaming as I pumped my dick into the sissy's hot, warm, moist mouth. His eyes were riveted on me. Cum was dripping down his chin. I felt like a god.

After what seemed like centuries passing, I finally seemed to be coming back to Earth. My orgasm was finally running out of steam.

But Gerri was still kneeling in front of me with my dick in his loving mouth.

Staring worshipfully at me. I slowly began to go soft. After a long time, he softly removed my dick from his mouth and gently licked and cleaned my dick and balls of all traces of cum. Like an obedient pet. I was unconsciously petting his hair again. He liked that. I could tell.

During the whole thing I remember he was moaning a lot. Passionately.

Estelle was petting his head now too. Beaming.

"Good girl. Good cocksucking girl. Now what do you say?"

"Thank you for letting me suck your dick Mr. Chambers. I loved it. You have such a sexy dick."

"You're welcome, Gerri. You're a wonderful cocksucker. Estelle is right." She was giggling again. Gerri was proud of this compliment.

"Clean him up Sissy. Then more drinks." Gerri got up off his knees and exited into the bathroom. I could hear water running.

"I think he has a crush on you," Estelle teased.

Then he returned with a warm wash cloth and proceeded to very lovingly wash my dick and balls. S'wonderful. I was flying.

When Gerri returned with our drinks I noted a real transformation in him. He was positively glowing with happiness. It was now obvious to me that he was very happy with this set up and lived for these little sex dramas.

"Now that I've shot my first load, I feel so much more relaxed."

"Good hon. It's always good to get that first cum out of the way. Now you can take your time. Savor it." I was still catching my breath.

"Gerri, get down here and eat my pussy. Watching you suck dick got me hot." He complied immediately. I envied him. Her cunt was very wet and smelled funky but oh so sexy. He nestled his nose into it. He obviously adored the fragrance of her excited cunt.

"Oooohhhhhhhhmmmmmmm."

"Yeah babe. Take care of mommy's pussy. Make me cum hard faggot."

Gerri ate her for about the next hour. It was great. Now and then she would squeeze his head in her thighs and scissors him. His face would get very red until she released him. Sometimes she would pull his hair or suddenly slap him viciously in the face.

"Eat it faggot! Suck Mommy's pussy."

My dick was hard again in no time. I was slowly jackin' my dick watching him eat her.

"I want you to watch me whip him sometime. It is so hot. It will be good for him for you to watch. And I want you to watch me fuck him with my strap on. He squeals with pleasure when the dick goes deep into his pussy. Just like a woman. A hot woman in heat."

After she came many, many times, Estelle finally pushed him away. Then she grabbed my dick and started kissing me on the mouth.

"Now I need a real dick. Put that big prick into me Sean."

No problem. I was into her sopping wet cunt in seconds. Pumping away.

Very very hot. It went on for a while.

"Gerri, lick his asshole! Get it wet for mommy." Suddenly I felt his femmy hands pushing my ass cheeks apart and then his wonderful, adoring tongue was licking out my asshole. Out of sight great feeling. Getting my ass reamed while fucking this sex goddess.

"Sean, have you got a present for me? Have you got a present?" I wasn't sure what she was talking about. Me cumming?

Next thing I knew Estelle was easing her long finger into my tender, wet asshole. I shot my second load in a long, long cum.

"Thas right, thas right. Shoot it out baby. Give it all to mommy. Give mommy that big load."

After my dick finally began to lose altitude, I pulled out of her sweet pussy.

Then lay next to her. Spent and sated. I looked at her cunt. Matted pussy hair and a lot of jizz pouring out of her.

"Gerri, would Sissy like a treat?" It was as if he was her pet poodle. And loving it.

"Yes Mommy. Please?" Here she opened her legs obscenely. Both knees bent. Her wet cunt the center of attention. Cum dripping out.

"Does the Little Sissy want to suck out all the cum? That the big dicked man pumped into Mommy's cunt?"

"Please Mommy? Please?" Gerri was loudly whimpering Estelle was loving this. I wondered how often this scenario was played out.

"Are you sure Sissy? There' s a big load of man cream up there. Is that what you want? All the cum that shot out of Sean's dick into Mommy's pussy? Are you sure?" Gerri was literally crying now.

"Oh God please Mommy!!"

"Get in there faggot! Clean me out!"

He dived into that pussy and commenced a very loud sucking and passionate moaning. She was smiling and petting him as he worked away on her pussy.

"That's my good girl. Suck all that nasty jizz out of my mommy's pussyhole."

She looked over at me while she was petting him, getting her cunt cleaned by her sissy cuckold husband. She had a demonic smile and looked genuinely happy.

"Sean, we are going to have so much fun."

CLICK HERE!!!

FREE SEX E-CARDS HERE