In for a Penny

"Sounds reasonable, but no whipped cream or KY?"

"I said that was her original plan. A couple of days later, it changed. Now she planned on being in underwear that Justin could cut off and I'd leave them to it. However, the next morning, I discovered they had been caught outside and Justin had freaked out. He wanted to stop the risky stuff. So, Izzy's plan escalated to win him over."

"How so?"

"Oh, let's start with that I'd cut all her clothes off her. I'd strip down to my underwear, and if he didn't freak out, I'd use her toy on her while she sucked him. If Justin wanted, she'd go down on me while he fucked her. Her only limitation was that Justin could not fuck me directly. He could go down on me if he wanted and use a toy on me but not put his dick in me."

"How did it go?"

"She had to get him rather drunk before he made out with her in front of me. But they loved it. It was a little disappointing for me. Despite her reassurances, he refused to touch me. So, after they collapsed into her bed, I snuck out and visited a friend to deal with my needs. A week later, we parted ways and I've not heard from either of them since."

"Regret it?"

"Not really. It could have been better, but we were young. However, this is where my comment about playing the same role twice comes in."

"How?"

"I need to talk to someone and see how they feel about something, and I'll tell you in a couple of days."

We'd reached her car, and I took her empty coffee cup as she got her keys out. Then she hugged me and kissed me on the lips. Her breasts pressed against my chest and her stomach pressed against my bulge. I grabbed her bum and pulled her harder against me. When we parted, I saw lust in her eyes, but she moved back. Damn, I hoped that might have gone somewhere tonight.

"See you soon Rowan. And I think you're right. You're nothing like Kyle down there."

I waited until she drove off and I sighed, went back home to wank myself off alone again.

Three days later, I visited the bar and saw Penny was busy and Kent, the owner, served me. Talking about football as Penny rushed about. She looked a little frazzled, but something in her eyes held promise.

"Fancy going to a wedding?" I asked her and held up the invitation to Crystal's and Kyle's wedding.

"Hey, we've not even slept together yet. And you want to get married?" She laughed.

"We can get that out of the way if you want." And I stood and started to unfasten my trousers. Earning a frown from Kent.

"Behave. Who's wedding is it?"

Kent moved off to deal with a customer as I re-fastened my trousers.

"Crystal and Kyle. So, the food and booze will be top quality."

I frowned as a knowing smile crossed her face.

"Are you asking me because you think you'll get lucky because it's a wedding?"

"No." I replied.

"Good, because I think you'll get lucky before that. If you're open minded that is."

"What do you have in mind?"

"Are you free on Sunday?"

"All day why?"

"I'll send you the address. And make sure you're not drained of..." She nodded at my crotch.

I left the bar with a big grin on my face. It was finally going to happen. The temptation to wank was overwhelming, but I wanted to be in peak condition. Drank lots of pineapple juice and water. Spent an hour in the sauna at the gym on Saturday and had an early night.

Sunday morning, I got a message from Penny with a map location that turned out to be a tourist cabin in the woods outside town. When I arrived I found Penny's car and another outside, which confused me. But as I stepped out of my truck, she hurried out of the cabin, wearing a robe, and rushed over to greet me.

"I suppose I should come clean. It's not what you think." My face fell, and I nodded to the other car and raised an eyebrow.

"We're visiting your grandma?"

"Nope. Remember that video of Crystal and my tale about my roommate?"

"Sure." I replied, but I'd forgotten about Crystal.

"After I told Crystal about the video, we sort of talked about the content and she was embarrassed as heck."

"Hardly surprising."

"So, I told her about my experience at college and about Izzy and Justin."

I suppose women talk about things like that more freely than men.

"Anyway, I'll spare you the back and forth, but I offered to help her fulfil her desires before the wedding. She's in there now and tied up."

"Excuse me?"

"That's where you come in."

"Refresh my memory."

"She wanted to be tied up, tick. Whipped, tick. And a guy with a big dick to fuck her throat and then her ass. I figure you qualify and would be up for that."

"Penny, why would you think I'd want to fuck Kyle's fiancée?"

"She's hot as fuck. You don't like Kyle and you'd be doing it for me. Afterwards, you and I get to have some fun. Call it an audition to see if you're man enough for me."

"I need to think for a minute."

"OK, don't be too long. When you come inside, follow my lead, and say nothing until I say it's OK."

I paced up and down thinking and remembered Kyle bragging to everyone that when he was married, his dad would give him a promotion and a massive raise. Which had pissed me off, as I was due for a promotion and had been told there was no additional money available. The idea of giving him the middle finger appealed, but in this case, it wasn't just my finger.

If you ignored Crystal's personality, she was certainly fuckable. But doing it in front of Penny and being judged on my skills was a little intimidating. Not that I had any worries in that area, but perhaps her standards were as high as her wild side.

Still, what did I have to lose? Unless this was all a setup? I'd go inside and find Kyle there to taunt me. I walked up to the cabin and my eyes widened as I looked through the window. No Kyle, but it might be Crystal. It was hard to tell. She was hogtied and kneeling on a low table with an eye mask and ball gag.

There were slightly red stripes across her back and buttocks. Which was obvious, as she wasn't wearing anything else.

As I stepped through the door, Penny held her finger to her lips to remind me to be silent and slipped off her robe. She was wearing a half cup bra that offered her bounty to the viewer and panties that I suspected were crotchless. Black, lacy, and very sheer. More like a flashing neon sign to her sex instead of covering it up.

Penny put her foot on the edge of the table and pressed. Causing it to rotate. Crystal let out a startled sound, but I was only interested in the view. She was curvy and her buttocks were inviting until I saw her pussy poking between her thighs. Her lips were puffy, and it looked like Penny had already used the vibrator that sat on the table between her legs.

As she rotated more, I saw how full her breasts were and how they hung from her chest. I also noted the nipple clamps and chain joining them, then hanging down. The mask covered her eyes, and the gag hid her sexy lips. I've no idea if she'd had work done on them, but a few times when I saw her, my first thought was to imagine them locked around my dick.

And it looked like this was about to happen.

"So Crystal, want me to continue?" Penny asked.

The girl grunted. Penny stepped closer and spanked the young woman hard upon the ass. Crystal yelled, then panted. But I noticed her wiggle her ass as if inviting more. Penny picked up the toy and held it under my nose, confirming it had already been used. She turned it on and ran the tip over the woman's back and buttocks. Pressing it between her legs, but not inside the bound girl.

Penny gestured I should come closer and took my hand. Folding my last two fingers away and placed my hand on Crystal's back.

"God, your skin is so soft and smooth." Penny said as she moved my hand lightly around the girl's skin.

I twigged Crystal might have otherwise noticed my large hand, so I went along with Penny. And prayed that Crystal was onboard with this, and I wasn't an unwelcome intruder.

Penny reached over and I saw her press the tip of the vibrator into Crystal just a little. Seeing her shiver, I was sure she was close to cumming.

"Do you want this big dick in your mouth now?" Penny asked and turned off the toy before unfastening the gag.

I snatched my hand back before the bound girl realised Penny had to have had 3 hands or very long arms. In order to caress her buttocks and remove the gag at the same time.

"Yes please. I've been a bad girl and need to be punished. Urb."

The last sound was Penny pushing the vibrator into Crystal's mouth. Any doubt that Crystal wasn't into this vanished as she bobbed her head vigorously. And trying to get it as deep as she could. But tied as she was, Penny had full control of depth and frequency.

"Ready to go deeper?"

Crystal nodded and tilted her head back. She gagged for a moment, and I saw Penny push the toy past the back of her mouth. It was held in place for 10 seconds and then removed. Crystal gasped, and panted, then nodded for it to happen again.

Penny gestured to me and mouthed 'strip.'

Well, it's now or never. Either I walk out now and regret it for life or...

Who am I kidding? I'd never walk away from this.

Penny's eyes lit up at seeing me naked which was a relief. One hurdle passed. She reached out and grabbed my erection and pulled me close. Examined it from close range, then looked me in the eye and lowered her mouth over it.

God, that was good. So good neither of us paid attention to Crystal until she made worried sounds, she couldn't breathe.

Penny pulled the vibrator out and held it next to my dick. And I smiled as outclassed it in both length and girth.

"Now, if I had a larger dick, would you want it?"

"Yes." Crystal blurted out instantly.

"And what would you want it to do?"

"Fuck my mouth and throat."

"And should that be caring and sensitive?"

Crystal shook her head. "No, I want to be treated like a cheap whore."

"Is that why you want it to fuck you up the ass as well?"

"Yes!"

"Hard?"

"God, yes. Please don't make me beg anymore."

Penny looked at me and then nodded to Crystal's mouth. Seeing her pouty lips reminded me of the few times I'd imagined her sucking me. Her smeared lipstick just made this hotter. I put my dick in front of her face, and it touched her top lip.

It was almost impossible for her not to know it was a real dick and not some silicone fake. She froze and tilted her head to the side as if to strain her ears to listen out for me.

"If you don't want it. I can send him away?" Penny said.

"No, I do. Please." She stretched her head out as far as she could and with her mouth open, strove to find it.

The moment she found it she wrapped her lips around it and seemed to suck me inside by vacuum alone. Penny's hand pressed on the small of my back and applied a little pressure to push me deeper. Crystal's tongue was all over me until I got to the back of her mouth, where she seemed to hesitate.

Penny reached under Crystal and did something that made the bound girl groan in a mixture of pain and pleasure. It took a moment to realise she must have tugged on the chain clamped to her nipples. Penny pushed me forward again, and I touched the opening to her throat when Crystal started to shudder and shake.

For a moment, I thought she was chickening out at the last minute, and I was about to pull out. Then Penny's nails dug into my ass and held me there.

"Another orgasm, and only from having it in your mouth."

Crystal nodded and shuddered again.

"I can't wait to see how you react when he fucks you properly."

Penny stood and caressed my backside, slapped it once, and kissed me. 'Enjoy' She mouthed and moved behind Crystal.

Under normal circumstances, and this was anything but, I'd have taken my time and gauged my lover's reactions and matched her needs. With Crystal, it was obvious what she wanted, and I slipped as deep as I could and pressed the tip to her throat, then stopped.

I'd hit a problem. Only two women I'd been with had managed to take it into their throat and one told me afterwards she'd never do it again. If Kyle was as small as she hinted in the video, this never would have been a problem for her, if he was even long enough to reach. However, I had an alternative.

Often, it's the lack of control and inability to breathe that causes the intense feelings. Counting to 10, I pulled back and let her recover.

"More." She asked, and I did, this time holding myself in place for 15 seconds and rocking back and forth.

I put my hand on the top of her head and counted down to zero, along with tapping my finger on her head. When I pulled out, I gestured to Penny about removing the mask and she shrugged.

Crystal blinked at the sudden light, and I could see her mascara had run. She looked up at me and frowned. It looked like she recognised me, but not from where. Which, as we'd only met a few times in a large crowd, was reasonable.

"Did you like that, Crystal?"

"You know me?" She sounded worried.

"Oh yes, we've met. I've often wondered about having those perfect lips around my dick."

The mention of my dick drew her eyes to it and overrode any doubts she had.

"Do it." She said and looked me in the eye as I fed her my dick again.

For a couple of minutes, I alternated between the deep thrusts, and letting her give me a regular BJ. At least until Penny joined in again. She brought the vibrator up between Crystal's legs and seemed to toy with the girl and not fuck her with it.

As Crystal became wilder and urged me to fuck her face, she was rewarded as Penny finally buried the toy deep inside the juicy pussy. The change in the pitch told me it was muffled by her flesh.

However, Penny was cruel enough to get Crystal close and then pulled out. Crystal whimpered that she was so close. But Penny had only stopped to grab lube and then slathered it over the toy. Pressing it against Crystal's rear hole.

"Last chance to change your mind?" She asked, and Crystal shook her head.

The yell she gave as the tip slid inside her went straight through my dick and I had to pull out. Partially worried she'd bite, but more that I might cum too soon. Crystal's head dropped, and she rocked back as far as her bonds would allow as Penny fucked her ass.

I stepped around to watch and Penny grinned and gave me a thumbs up. Then reached for my dick and spread lube on it, before wanking it with one hand in time to her fucking Crystal.

"Go get her slugger." Penny said, in a surprisingly manly impression, and slapped my butt like some baseball coach.

For the record, I'm not into causing anyone pain. And I would have quit if Crystal would let me. Over the next few minutes, Crystal was crying out in pain and swearing, but refused to give up until I was buried to the hilt. When she asked if I could wait for a minute for her to get used to it, I was more than happy to comply.

Mostly I needed a break because her rectum was gripping me so tightly and pressing down with such heat. I wasn't sure how long I'd last. And my performance here had a direct standing for the chance to be with Penny.

I'd just started rocking back and forth when Penny returned from the bathroom, having washed the vibrator. She gripped my hips and used me like a giant sex toy to fuck Crystal's ass. I was trying to think of anything to distract myself, which was hard, as Penny's nipples seemed to bore into my back.

Then Penny dropped and used the vibrator on Crystal's clit. Crystal was panting and swearing, grunting, and making sounds that would puzzle a coyote. It came as some relief that Crystal climaxed again. As her anal clenching gave me just enough pain to bring me back from the brink.

After pulling out, we helped her lie on her side. There was drool and snot around her mouth and nose, and she seemed out of it. Getting a handkerchief from my jeans, I cleaned her up.

"Pick her up and put her on the bed." Penny said.

I realised the rope that tied her knees and elbows together was platted and reminded me of a strange hippy handle for the weirdest piece of hand luggage. I strained to pick her up with one hand and she dangled before I swung her up onto the bed. Wondering what airport security would say if I tried to get her through the scanner like that.

Penny unfastened Crystal's arms and swung her legs over the woman to pull her legs up and gestured I wasn't done. Noting Penny's split crotch panties now showed her shaved pussy, I pressed back inside, far more easily. Crystal moaned briefly in pleasure. The pleasure wasn't brief, but the option to moan was, as Penny pressed her shaved pussy down over the girl's mouth.

Penny let out a gasp and I could see the underside of Crystal's jaw as her tongue was lashing at the pussy pressed on her. Penny tugged on the chain attached to Crystal's nipples and I saw she had pierced nipples with little hoops on them. So, Penny had simply attached the thin chain to her jewelry. I've no idea if that was better or not.

But seeing her tits lifted by the chain and flopping about as I pounded her ass was a sight that brought on my climax. But Penny was ahead of me. And handed the vibrator to Crystal and told her to use it on herself.

She took it and rammed it inside, hard and fast. Feeling it through the thin membrane and the extra tightness was uniquely stimulating. She shuddered again as she climaxed. The feeling combined with the vibration was enough for me.

"I'm gonna cum soon."

"On my tits." was the muffled reply from Crystal.

Penny lifted off and lifted Crystal's head up to watch. I pulled out and leapt onto the bed, straddled her stomach, and shot my load all over her perfect tits.

When I got my breath back and looked at Penny, she gave me a smile and a nod. That seemed to signify that I'd done enough to satisfy both women.

"Go clean up." Penny said, and I went to the bathroom. I turned on the shower while Penny washed the toy again.

"Just for the record, you passed. Next time, it can just be the pair of us."

"Do I get to tie you up?" I joked.

"I was hoping to do that to you." She dead panned back.

"Not with that vibrator you won't." I replied, more than a bit worried.

She pouted and feigned disappointment. "I'm sure we have enough by ourselves to have a fun time. I'm going back. I'm owed at least 2 orgasms."

I showered, taking my time, to be thorough. But the thought of Penny and Crystal together resurrected my dick quicker than usual. When I returned, I found Penny naked on her back, with Crystal kneeling on the edge of the bed and eating her out like it was the last ice cream on the planet. Penny blew me a kiss and pointed at Crystal, then mimed, I should fuck her.

Why hadn't I thought about that? Oh right, I had.

Dropping to my knees, I pressed my face between her thighs, flattened my tongue and ran it the full length of her lips and then stood and pressed the tip to her pussy. Waiting a moment before she pushed back and demanded my dick. Unlike the previous times, when it had been hard and fast, I was slow and gentle. Not wanting to distract and ruin Penny's pleasure.

I'd no idea if Crystal had ever been with another girl, but she knew what she was doing as Penny's orgasm was explosive. When she recovered, she spun around on the bed and vanished under Crystal, and I realised Penny was sucking on the other girl's tits.

Our fucking got faster, and she blurted out that I should cum inside her. Not a moment too soon as I fired off my second load of the day, and Crystal followed suit moments later.

When I pulled out Crystal, despite having the post orgasm flush, jumped up and hurried to the bathroom, looking embarrassed. Penny went to check on her and returned a few minutes later.

"She's embarrassed now."

"Does she regret it?"

"No, at least not yet. But having a guy who knows her do that, is giving her a hard time. You should go."