Penny's Freaky Friends Ch. 1

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A group of uninhibited folks initiate a new member.
3.4k words
4.11
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Part 1 of the 3 part series

Updated 11/01/2022
Created 10/28/2001
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My new fried Penny invited me to a "freak friend party."

I had met Penny at work and we had started talking. Slowly over a few weeks it turned out we both liked the same things. Well, specifically one same thing – sex!

Penny was 36, a BBW lady, but very pretty, with huge eyes and a gorgeous smile. And she had massive tits, lol. I wanted her tits in my mouth. I wanted my hands to caress those massive jugs, and I wanted to tit fuck her so bad. I had told her this, and she had suggested we get together one night to do it. She admitted she loved her tits played with, and was always looking for some fun. Hell, I wanted to fuck this lady so badly.

She told me she had several similar-minded friends and they were planning a wicked night of debauchery soon. Would I be interested in cumming (sic) along, lol? Sure, I replied, and we set it up for the next weekend. I love sex, and was game to try anything new.

I wasn't sure what to expect, and Penny was vague too, but she did tell me that only those new people that everyone "liked" ever got invited back for a second visit. I asked who her friends were, and what went on, but she just laughed. All she would say was that I would get all of the sex I could dream off, and they only had one rule – no pain.

What the heck? I was game to try anything once.

I got the address, showered, shaved (top and below), dressed casually and set off for Penny's house.

She lived north of town, in a rural setting and the house was shrouded by trees and very isolated. In fact, it took me about 20 minutes to find the street and her driveway. When I arrived I counted 5 other cars parked around her house. 4-5 other people, I thought (counting one person each car, and one car as hers), ok I can deal with that.

My first of a hundred shocks that night was how Penny greeted me at the door. She was naked! Her tits bounced as she walked up to me, and she was smiling and laughing. The second thing I noticed was her tits were tied up. She had a piece of rope tied around each tit like a halter.

"Hey, Bob" she laughed, "I told you it would be sexy tonight. Pick your tongue back up from the floor, lol" and she turned and walked ahead of me back into the house.

Her ass was large but cute, and I imagined getting my mouth close to that too. I knew my cock was already hard but who cared, lol.

Penny led me through the house to a large room at the rear. Soft music filled the air, and cigarette smoke wafted around. The next shock I got was that everyone in this room was naked, and there were 10 people there. All ages, all sizes, and all sexual preferences too. I knew from her description that this was a "sex party," but somehow I thought the sex would occur discreetly, behind bedroom doors, with people moving in and out at will. I didn't expect them all to be in one room, watching.

The next shock was a jolt. She turned to me, told me to undress and handed me a dog-collar to put on. My freshly erect cock shrank away to nothing!

"Bob, you are the new "guest" here tonight. Our rules are simple. You are my toy for the night, and anyone can do with you as they want to. Are you willing?" she whispered seductively to me. "I should tell you about our rules before you answer," she continued. "We do not do pain here, we might stimulate you, and that might cause initial discomfort, but no overt pain. And we don't demand you do anything you don't want to do, either. We will understand if you say no to anything asked, but, if you do refuse, you won't be invited to join us as a "member." Are you willing?"

"Sure," I said as I slipped out of my t-shirt and shorts. I knew roughly what was going to happen tonight, so I dressed accordingly. As I said earlier, I freshly shaved my cock, and had no underwear on, so two garments later I was as naked as everyone else, and as fresh as a new born.

I let Penny put the collar around my neck, and she left it loose. As she put it on, I felt her tits brush against my arm, and my cock sprang back to life. She leaned forward and whispered quietly in my ear "My cunt is the last thing you get tonight, but only if you are a good boy, ok?"

"Ooh" said one lady, about 60 (or so), as she watched me grow erect, and a similarly aged man, close to her, licked his lips and started stroking his cock.

What was going to happen? I was both excited and scared at the same time. One part of me wanted to run for the hills, and another part wanted me to run to the tits of the first lady around, lol. If cock was offered tonight, I would be happy, if it wasn't I knew I would still enjoy this night.

"The rules were going to be simple," added Penny. "I will lead you around as my toy, stopping at each person. They will then either ask you to perform, or will just seek to perform on you. You are totally in control at all times. Do you understand, slave?"

"Yes" I replied, and she pulled the leash attached to the collar tightly.

"Yes, what you little shit," she hissed.

"Uhh, yes mistress?" I asked.

"That's better, and never forget it." She sternly rebuked.

At that she led me around the room in a parade" of sorts. Letting everyone in the room see me up close, and look me over. As I said there were 10 people lounging around in this large room. Mixed evenly between men and women, and aged from young to old. Several appeared to be couples, and at least two guys were holding hands as I passed. Two women were locked in a steamy embrace and Penny kicked one of them to get their attention.

Counting Penny and my self there were 12 people in the large room.

I was going to be a busy boy tonight!

Almost immediately I was approached by a mature aged couple – the ones I first saw as I entered the room.

"Dear Mistress Penny," she said. "May we be the first to enjoy our new friend? Our ages are such, that late nights tend to leave us weary, and we don't think we can wait until the last of the night."

"Of course, you can" Penny casually said. "Hey everyone, watch Ronnie and Flo enjoy our new toy."

All eyes fell to the three of us, and I stood there waiting. Was I supposed to make the move, or where they? "Flo" took my hand and led me to a large cushion on the floor. She asked me to kneel forward on all fours and I did. "Ronnie" came up to me and smiled at me, and asked me quietly if I sucked cock. Yes, I told him and no sooner had the words left my mouth, than he knelt in front of me and stuck his cock into my mouth. Mmm. He was not large, nor small, but his cock tasted nice. If I didn't know better, I swear I tasted cunt on it? He slowly pumped in and out of my eager mouth.

Applaud filled the room and everyone was laughing and clapping.

As I knelt on all fours I felt a hand reach around my ass and start to stroke my anus. Flo?

She started to rub my asshole, and I felt one finger go into my hole. Ahh, I pushed my ass to meet her hand. She slapped my ass hard!

"You little fuck," she hissed. "I am doing this, if I want your fucking help, I will tell you!"

She then inserted a second finger into my awaiting ass and started to finger fuck me. I admit this wasn't exactly what I thought would happen tonight, but I wasn't about to jeopardize my whole evening with the first people.

My head was still forward, sucking Ronnie's cock earnestly, and I could only sense what Flo was doing to me. But I felt a tongue lick my ass hole s her fingers kept up the fucking, and I felt her other hand cup my balls. I was being given a finger fuck, and a rim job by a 60 year old lady as her husband(?) fucked my mouth.

"Ronnie, you old cunt," she then said. "don't go wasting that precious juice on his virgin mouth, I got his ass nice and wet for you. Come on fuck his hot hole." And he pulled his stiff cock out of my mouth and rose to go around to behind me. I braced my self, for although my ass wasn't a virgin, it had only known toys and not flesh. But Ronnie slipped effortlessly into my fuck hole and started to pump rapidly into my waiting hole.

Flo stood, walked around to me, and knelt in front of my mouth. "Ok, mister stud," she said. "Give my honey pot a good tongue job." And she stuck her ass into my face. Her ass smacked into my mouth and I could do nothing but lick. I put my tongue into her ass crack and started to lick her out. Ronnie was fucking me from behind now, and I was rimming her out. She lifted her hips a little and now my tongue found her wet cunt.

She pushed harder and I thought I would smother. But I never stopped licking her cunt out either.

"STOP" called out Penny. And they both moved away from me. Ronnie's cock still purple and hard, and Flo smiling contentedly "Ronnie take that rod and fuck your wifes hot cunt, NOW!" commanded Penny. "And Bob, come with me."

As I stood I saw Flo go over and suck at Ronnie's cock for a few seconds, wink, and then she turned and knelt down in front of his cock, as he slid his cock into her wet cunt.

Penny took my leash again, and we started walking. "Bob," she said. "We would be here for days if everyone kept fucking you. They will all get a chance with you to get aroused, but they can then go off together to finish off. Ok?"

"Ok" I answered as I wiped my mouth.

My next "host" was a young lady of about 20. Petite, and pretty. Long dark hair, small tits, and a nice bushy cunt. "Hi, Bob," she said. "I am Laura, and I like to kiss and fuck. Will you fuck me please?"

"Sure," I replied, and she lay down and opened her legs for me. I gently lowered myself until I felt her hands on my shaft, and she guided me into her waiting wetness. I kissed her neck and chin, and she gently rocked me as I fucked her.

As we fucked, she talked quietly into me ear "Oh Bob, this is fun. I love coming here. My first night was so frightening, but everyone is so much fun. No one will hurt you, just relax and enjoy it." She said. "I love fucking and I get so many different cocks here. I love it here. My boyfriend will probably get you to suck his cock after he fucks me. Please do it for me, please? Please taste my cunt on his cock for me?"

This little lady was a tight fuck, and an experienced fuck too. I felt her cunt muscles control my cock, releasing and tightening as I stroked in and out of her.

Again (before I could cum), Penny stopped the "show." Fuck, lol.

I thanked Laura, and kissed her gently. As I stood I watched a young man approach her and without even asking, enter her. They started to fuck briskly and determinedly. He groped her tits and pulled and twisted her nipples, as she shrieked in happiness. She tore at his nipples too, and very quickly he came in her. Both of them seemed to pause, then slump.

He pulled his cock out of her, beckoned me over, and told me to kneel in front of him. He then pushed his shrinking cock into my mouth. Ahh, she did taste wonderful, and I greedily licked all of her sweet nectar from his cock. I looked out of the corner of my eye and she was sitting smiling widely. She was also fingering her cunt, and licking her fingers. Every time she did, she looked at me and winked. He never did recover his erection and in short time, he pulled his shrunken cock from my mouth. She did taste amazing.

Four down. . . . Next!

An old couple, a young couple, some oral, some anal, I was coping well so far.

Penny then led me to a lady of about 47, who was stroking the tit of a second younger lady, as she kissed her fully, and aggressively. As Penny handed then the leash, the older lady tugged hard and I fell to the floor in front of her. "Kiss this slut" she whispered, and pulled at my left nipple.

The younger girl, around 30, looked at me, and said nothing. I leant forward and kissed her gently on the lips. "No you prick, I want it to be a hard kiss. Do it now!" And she pushed my head towards the other lady. I felt my lips press against her lips and the older lady held both of our heads. Finally, she released us and we both sat back breathing heavy.

"Now, little man, I want you to pull her tits, and make her scream. And she better fucking scream or I will kick you in your inferior little balls." The younger lady, nodded imperceptibly, and winked at me. I took both of her nipples in my hands and started to pull. Nothing! I pulled harder. Still nothing. Fuck.

I started to twist and pull hard on both tits, and I must have been hurting her, because I saw her wince, but still she refused to cry out. Oh fuck, I thought. Finally, I pulled down harshly on both nipples, pressing hard and she whimpered.

"Little man, you amaze me. Damn, the little cunt usually never gives in. Fuck." She said then lowered her mouth to my own nipple. Fuck she hurt. She bit me and I swear she drew blood, but when I looked there was only a red mark.

Penny grabbed my leash and I was off again. Just in time, I reckon that one would have bitten my tit off.

I knew inevitably I would meet the gay couple, and I also (hoped that I) knew what would occur. I hoped that Penny would lead me to these guys now, so I could get it over with. But no, damn, she led me to the last, but one, couple in the room, bypassing the two gay guys. They looked peeved, but let her pass them.

I say couples, but in fact, apart from Flo and Ronnie, and Laura and her boyfriend, I didn't know any of these people, and for all I knew they had simply paired off for the fun. They might have been couples together, or had just coupled together for tonight?

This next to last couple were ordinary looking – both holding hands and cuddling, he was about 35, and she was similar aged. She had very large tits, with dark nipples, and he was about 8 inches and thick. Neither were startling in any other way.

"Bob," he said. "I want to suck your cock. May I?" he asked quietly. "and while I suck your cock, my wife wants to suck me, but when you are ready to come, she wants to take you in her mouth, please."

And without waiting for an answer, he lowered his head to my stiff cock. She similarly lowered her head to his member, and as I stood peacefully, I watched him suck me, as she sucked him. As she was sucking him, she slowly turned her body around so he could reach for her cunt. I then watched as first one, then two, and three, and finally all of his fingers buried themselves deep in her widening gash. Finally he pushed his thumb into her cunt, and started to fist fuck her, as she calmly sucked his cock. Man, I was ready to blow my load right now.

"STOP" cried out Penny again. Fuck, this lady knew how to fuck up a good time, lol.

Without waiting for approval, she jerked my leash away, and we were walking again. I looked back over my shoulder to watch the two of them still go at it. She was hungrily sucking his cock, as he fisted her deeply and brutally. She was smiling and laughing and he was breaking out in a sweat from the exertion.

All that was left were the two gay guys, surely. Penny wasn't going to miss them was she? Finally, she didn't disappoint me. They both stopped holding hands, and smiled as Penny led me to them.

"Jack and Tony are our resident gays." She said. "They enjoy new meat very much. Now boys, be nice, Susan over there was a tad ornery with our new toy, and we don't want any more damaged goods, lol." She laughed as she stepped back to let them have me.

They motioned me over, and as I got close they stood. They told me to kneel, and I found both of them were standing with erect cocks. Both motioned me closer, and one by one they pushed their cocks into my mouth. I was sucking two cocks!

As I sucked them, I looked up. They were kissing, and stroking each other's tits. I didn't care. I had two cocks in my mouth (a first) and I wasn't about to lose the opportunity. They continued kissing and arousing each other, and I felt a hand on my cock. Laura's soft voice whispered, that she was going to please me because I had pleased her. At that she lowered her head to my cock, and started sucking me. Her boyfriend also came over and started to kiss my tits and gently pull my nipples.

I was not going to complain. I hoped to god Penny would not interfere, lol. Laura, although petite, was giving my cock a strong session. She was sucking me deep into her mouth, and jerking my rod simultaneously. It was only a matter of time until I came, especially with her boyfriend sucking my nipples, and pulling on them. The two cocks in my mouth were twitching, signaling their imminent explosions.

I looked around me – the two lesbians were 69'ing each other. The young couple were still fisting and sucking and Ronnie and Flo were masturbating each other.

Penny was the surprise of the night. I felt her push at my ass, and as I stretched to see, I noticed she was wearing a huge strap-on dildo. She had lubed it up, and was now pushing this monster into my butt. It went in and I gasped. I didn't want to lose the two glorious cocks ready to cum, but I was now concentrating on her assault of me. The dildo must have been 10 inches long and thicker than any cock in the room, but she just pushed and pushed until she was fucking my ass.

It was too much. I came hard in Laura's mouth, and felt the two guys come simultaneously. I slurped and licked and swallowed their joint cum, and watched Laura swallow all of my load. Her boyfriend rose up and kissed me and Penny kept fucking my ass.

Finally Penny pulled her dildo out and I collapsed on the floor. Everyone stopped and applauded.

One by one they came over to me, naked, sweaty and wet with sex. They all kissed me, and I felt hands stroke at my body. Would I get invited back? I hoped so.

Penny leaned into me and whispered "Now, Bob. My cunt is wet and waiting. Are you up to it?"

But that's a story for another time, lol.

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