In for a Penny

We went shopping again. Mortimer is just going to hate this even though it's not his money. I did send him a preemptive text this time. 'Do you want the lingerie pics as proof of purchase?'

'Asshole.'

I glanced up from my phone in time for the next modeling run. She asked me if I wanted to see what she was picking out. I made the terrible, world's worst mistake, of telling her yes. She came out and modeled every bra and panty she bought. And most of them I had to look close to see if she was actually wearing something.

About halfway through she sauntered to me and leaned over putting her hand on my aching cock as she almost spilled out of her bra. "Should I model the half cups here or at home?"

I reached up and cupped her tit as I responded expecting her to react. Well, she did, just not the way I was expecting. She pressed into my hand instead of pulling back and moaned when I told her if she did she was going to be bent over screaming in orgasm in the middle of the store soon after.

She got several nice tops and slacks, then she peeked around the corner of the changing room door and slithered out and onto my lap. "Acceptable?" she whispered as her lips caressed my ear.

I tipped my head and lightly kissed the upper slope of her tit. I could do that because she had a strapless corset top on that made me want to just eat her up. "Fucking hot."

"Not too much?

"Absolutely perfect."

"For Saturday?"

I brought my hand up to cup her barely encased tits, "Only thing better is if your nipples stood out a little. My brothers would have a heart attack right after their tongues hit the floor."

"I can do that if you want me to." She was grinding on my cock making it hard to think.

"Only if it won't bother you."

Penny pulled back to look into my eyes. "Do you like seeing my nipples stand out?"

I couldn't answer, but I could stop smiling.

"Barely there, noticeable, or blatant?" she said in a husky whisper.

"Noticeable." I managed to get out.

Penny wrapped her arms around my neck and went tonsil hunting.

"You don't mind?" I asked her when we came up for air. "Being looked at?"

"If you want to look, then so be it."

I chuckled. "So I shouldn't have postponed having a dinner party with you as my naked hostess then?"

Penny hissed and jumped back up and dashed to the changing room.

She came out a few minutes later. Still in her snug slacks, but the corset top had been replaced with a loose thin gauzy top. Her nipples standing out and more than just a shadow of her areola. I looked, Penny pulled her shoulders back to put her tits even more on display.

"I'm really torn between walking around to show you off and hauling your ass home and bending you over the couch to fuck you silly."

Penny's eyes fluttered, "Why choose?" came out in that husky whisper again.

I groaned softly, she grinned at me and put her arm through mine. We strolled the mall for over an hour. Every male beyond puberty looked at her bouncing tits and nipples. Almost every woman gave her a dirty look for getting their man's attention. Almost. There were three dressed just as hot that grinned and shook their tits. Penny giggled and did the same, then looked quickly at me. "Was that okay?" she asked in a timid voice.

"Would have been better if you were topless."

Penny reached for the hem of her top and started lifting. I managed to stop her before her tits were exposed, "But that would get us arrested." She stopped and looked at me. "And then I couldn't bend you over the couch when we get home."

She let go of her top and took my hand. "We need to go home."

Penny leaned toward me as soon as we got in the car. She pressed her tit to my hand as I reached to cup it. When I needed both hands to steer, she lifted her top to bare her tit when I reached back. Eyes closed grinning.

The kid in the next lane honked and gave me a thumbs up. Penny didn't open her eyes, but she did keep grinning.

She had to pull her top back down when we pulled into the parking garage, and we had company in the elevator for the first few floors. When the older lady giving her the stink eye for letting her tits out to be appreciated got off she growled, "You need a place with a private elevator."

"Why, so when I want you topless you don't have to worry?"

The top came up and off and she backed into me pulling my hands to her tits, "Exactly."

I groped and massaged. I thought we had a problem when the elevator stopped on the way up, but there was no one there. But that just revved Penny back up when I tugged on her nipples.

We made it to my apartment. "Couch, now!" I said and pointed to it.

Penny squealed and practically ran to the couch, dropping her slacks as far as her thighs before bending over and reaching back to open herself.

I roared as I stepped to her. My slacks didn't make it much further than hers and I drove into her like a mad man. I had a hot babe in my hands, rubbing on me, and showing her body off for the last several hours.

Penny just plain got FUCKED!!!!! I came almost right away as she was screaming. But the last few hours had given me a charge. I just kept right on fucking her only going firm before coming right back to cave man hard. I fucked her hard, I grabbed her ass, I reached for and played with tits and nipples, I gave her a few flat handed swats on her ass that just sent her into orbit getting her another round of ass slapping fucking.

Exhaustion was overtaking me, and I rolled us over the back and onto the cushion, landing with me still on her back, cock just barely in her pussy. I reached for a tit and Penny lifted enough for me to get my hand in before she collapsed on it and I passed out.

I was still on Penny, my cock had slipped from her pussy but was hanging in her keyhole... and she was whimpering.

"Penny, I didn't mean to, um what did..."

She took a deep breath, "I'm okay, just a bit overwhelmed."

I was relieved, "Okay."

But when we disentangled everything was not fine. Her eyes were puffy and bloodshot, she had obviously been crying. All I could do was look at her eyes and caress her cheek.

Penny put her hand on mine and smiled, "It's not what you think, but we do need to talk about it."

We took a shower, and I washed her softly and slowly.

We got something to drink, and she pushed me to the corner of the couch and then curled up in front of me pulling my arms around her. "This could take a while, please be patient with me."

I lightly kissed the side of her neck, the top of her shoulder, and held her a little tighter. It was all I could do not to reach down and cup those tits, but I did resist.

"I'm sure Morty gave you a bit of history on me."

"He hit the highlights in his usual crude manor."

That did make her chuckle. "Well, I started out like a lot of starstruck women. Left high school and headed to California to make my fame and fortune."

I chuckled lightly.

"Yeah. So after a lot of waitress jobs and such while I was waiting to be discovered, I answered a casting call for an R-rated movie with my roommate. We didn't get any parts, but I got a call from the casting office a few days later. They had another movie they wanted me to consider." She took a deep breath, "It was an X-rated movie."

"The offer couldn't have come at a worse time. I was a week from having my car repossessed and being kicked out of my apartment. I hid my car at a friend's house, talked my roommate into giving me another extension, and went with head hung low to make my money."

"The first one was hard, I had to fake everything and even then we had to redo some scenes. But I made it through it, paid off my debts, and even paid ahead a little. And then the next call came, and the next and the next."

"I got some advice from one of the former actresses, getting the piercings and tattoos so they couldn't use body doubles and making sure I was paid for stuff I was in." She sighed, "Sad to say I was getting into it. A lot of it was fake, but some scenes were pretty real, us really getting into it. They were my rose colored glasses."

"I was rolling in the dough I thought, but getting into more and more hard core stuff. I could say no in the office, but on set it was like I was compelled to do things. It took several years before I had the nerve to talk to someone about it."

She tipped her head back against my shoulder and stared at the ceiling for a bit before continuing. I took advantage of the situation to lightly kiss her shoulder. I got a nice soft sigh from her.

"Basically, I'm a throwback, a cave woman. Tell me to do something and I'll pretty much do it. The shrink called it being submissive. I'm not into bondage and pain and all that stuff. And if you tell me ahead of time, there is a good chance I'll come to my senses. But on the spot, if you tell me to strip, drop, and deep throat your cock in front of your mother and I'll do it without thinking about it and get off on it at the same time."

"EWWWWWW."

Penny snickered, "Okay, bad example. Downtown Christmas day at high noon."

"Better, kinda."

"So earlier, when you bent me over and had your way with me. I wasn't hurting, I was out of my mind with pleasure." She paused, "Weird huh?"

"Everybody has their quirks." I let my hands come up until it was just my fingertips playing with her nipples like little joysticks. I smiled, an apt analogy.

Penny wiggled back against my firming cock, "That's a common one with men."

I chuckled, "Yeah, I'm guilty." I rolled them between thumb and finger making Penny sigh. "I guess it's part arousal, part instinct. I know the arousal part is not always real. There are women like you that have nice firm nipples all the time even when they are not aroused, and I dated a woman whose nipples never, ever, stood up. Barely a little bump even when she was screaming to the hills in orgasm."

Penny snickered and pushed out into my hands. I used her tits to pull her back into me making her sigh. "That's why I got out of porn and into escorting. Basically, high price short term private porn. I knew what was coming, and I knew it was going to be over pretty shortly."

She gave a BIG sigh, "That conversation I overheard, when Hunter was going to have a couple of guys knocked off." Another BIG sigh, "I was spread eagle on the bed, a ball gag in my mouth, a big vibrating dildo in my cunt, and two pillows under my hips to put my ass in the air."

I was picturing that in my mind, and between a rock and a hard place reacting to it. The scene was fucking hot to imagine, but imagining Penny tied up like that killed the hot.

"And I wasn't tied down, I prepped like that for him," came out softly and slowly. "Because he told me to," barely above a whisper.

I was staring at the wall, and Penny was quivering in my arms. I had no fucking clue what to say.

"Hillary showed up a little later, and we spent the rest of the day getting our asses fucked. Sometimes in a sixty-nine, other times in line with a face in the others cunt." She snorted, "But we had to keep the dildos in our cunts to make it feel like Hunter had more than a little hot dog between his legs. I'm not positive I would have actually felt him in my ass otherwise."

It took a second, then I had to laugh. That was the worst comment a woman could make about a guy. Small enough she wouldn't know for sure if he put his cock in her ass.

When we finally quit laughing I took a long slow series of kisses on the top of her shoulder headed for her neck. "I hate to say it, but you may be disappointed in me. I'd venture to guess I've had more sex in the last few days than since I first got laid."

"You heard Hattie's opinion of my sex life," I continued. "I've had the few odd girlfriends, but not a lot of sex. The usual missionary, doggie, eating pussy, and I thought I'd had a decent blowjob until you swallowed me down."

That made her giggle.

"Then you tell me that if I told you to, you'd not only bend over and spread your ass, but enjoy a good hard fucking as well." I had to stop and think, "And you're into women on top of that. I mean it is the ultimate man's fantasy, but I'm not sure I can get my head around it."

"I can't say I'm into women, more like into being with a woman for you."

"Okay," I said slowly.

"It's not the being with her that I enjoy, it's the looks I get from him as he watches us. Trying to do things that will get him off."

Ah, that made a little more sense. "I can try and not be so suggestive."

Penny took a deep breath, "Or my husband can use and display his willing wife."

That took me by surprise. "Really?"

"I'll try and not pop my tits and nipples out around your family, and you try and not put me over your knee and spank my bare ass." Penny giggled, "Well not my bare ass, maybe a thong at least."

We cuddled and kissed a bit as we talked the little things out, then Penny stood and went toward the bedroom. "I'll meet you in bed."

I heard the shower start, and crawled into bed with a raging hard on. The shower stopped and started a few times, then Penny came out looking squeaky clean and radiant. Then she surprised the holly hell out of me.

Penny stopped just barely on the bed and lifted my cock. It took me a moment to realize she was lubing my cock. She wiped her hand and crawled up beside me, face in the bed, knees tucked under to her tits, and ass in the air. "Take me husband," she said softly as she spread her cheeks.

It was an eternity and a flash. I was looking at her and jumping up behind her. Her ass was lubed and slightly spread. Penny groaned softly as I put the tip of my cock against her. I was nudging a bit when she got impatient. I was nudging forward and Penny slammed back taking me to my balls in one stroke. "Yessssssss," she hissed.

Well fuck this. I grabbed her hips and just slammed into her ass over and over. Both of us screaming and cumming until I collapsed on her with my cock still twitching as I held her tight. It was different having my cock still trapped in her ass even if I was going soft. She giggled when she rolled away making me pop out. She got me standing and us to the shower. I was cleaned and entertained. It is so fucking hot watching a woman shower for you.

We cuddled and we groped, and I tried to get used to it. It would take me a long time to get used to a woman wanting to be told what to do. To put her body on display, or to be used for my sexual satisfaction.

Penny was spooned in front of me, my firm cock in the crease of her ass. "So was that good for you?" she asked wiggling that ass back against me.

I was glad she was in front of me so she couldn't see my face. "That's the first time I ever... well... um."

That ass was picking up speed moving up and down my cock. "So we'll have to try it a few more times to see huh?"

I gave her tits a soft squeeze, "But you enjoy it."

"Mmm, yeah. It's not like I hate it, but I'm not some ass slut either." She put her hand to her mouth giggling.

"What?"

"Remember I said Hillary and I spent our day getting our asses fucked?"

"Yeah."

"Well that old broad was a certified ass slut. She'd whine if she had to take a cock in her cunt, but got off on the guys fucking her ass. She was depraved enough to suck that cock clean after it had been in her ass or anyone else's."

"EWWWWW, that's just plain sick."

"Yeah, she and her husband were quite the pair. She wanted cock in her ass and throat, he wanted young flat chested girls that looked under age. They'd gang up on some eighteen year old and he'd fuck the kid's ass then she'd slurp him clean so they could start all over again. She'd pass out when he fucked her ass and pushed her face into the kid's cunt while he did it."

"Wow," was all I could say.

"Yeah, there are some really sick puppies out there, and most of them are the ones you'd never expect. All prim and proper out and about saying shit about others to deflect from themselves and their nasty flip side in the bedroom."

"Did you ever..."

"I only met him once and didn't know it at the time. Having him in my ass was no big deal, as in really no big deal. It was okay, but he'd get lost in even a decent cunt. Barely long enough to hit my throat."

I didn't know if I should groan or chuckle at that.

Penny pulled away, rolled me to my back, then turned to take a much closer inspection of my cock while her glistening pussy was just above me. Her soft moan as she slowly took me to my balls was almost a religious experience.

She licked a little at the head of my cock as she slowly but firmly stroked me. "So what kind of things have you thought about doing with a girl?"

"I... Um..."

She took a sloooooow lick up the underside of my cock. "So let's eliminate all the usual's. Deep throat, anal, and three ways." I twitched. "We can do those anytime." I tried not to twitch again.

"Titty fucks?" that came with a not so slow lick.

"Tried it once, no twice. Didn't work with little tits, she had to hold my cock in her cleavage. The big tits were okay, but they were starting to sag and came with big everything else so no."

"Where'd you cum with them?"

"Tissue and cleavage."

"What, no painting tits and faces?"

The stroking was picking up speed and I was hard.

"Isn't that one of the all-time male fantasies? Standing above a woman stroking that hard cock as she watches his hand while she plays with her body for him. Feeling his eyes following her fingers as she goes from tits to cunt and back. And when you're ready, what would be hotter? Shooting all over her tits, or seeing her with her mouth open wanting you to cover her face?"

I pulled that engorged pussy down to my face as I erupted between her lips. Stroking my cock when her lips were wrapped around the head sucking the very life out of me while I did my best to drink her dry.

I woke being lightly kissed. "Might have to try that a few times to see what you like better." She pulled up right beside my ear, "I'll try not to squirt too much when you cover my face."

- - -

The next two days were torture, pure unadulterated torture. Penny was in and out of the bedroom trying different outfits on to see what I liked. Then it was down to what bras and panties / thongs / g-strings I preferred. Of course, bra trials were bottomless, and vice versa for the bottoms.

I tackled her and hauled her off to bed at least twice daily, and that was before the evening shower.

Saturday morning we slept in, well, we stayed in bed. It was difficult to crawl out and take a shower after two hours of passion.

I slipped on some jeans and my old college sweatshirt. Penny came out and all I could do was stare. It wasn't fancy, but it was HOT.

Simple jeans that clung to her ass just enough but not too tight. A dress shirt without pockets just thin enough to show the lace bra. That in turn thin was enough to let her nipples stand out a bit and a good shadow of her dark areola.

She came up, gave me a soft kiss, then put her head on my chest. "I take it you approve. I wasn't sure if I darkened my nipples enough or if I should have done them darker."

I groaned, "My brothers are going to want to eat you alive and their wives are going to want to kill you."

Penny tipped her head up grinning, "There's only one brother's appetite I'm worried about, and so far he's eating just fine." That was said as she ground her mound against my hard cock.

"If we don't get going I'm hauling your ass back to bed."

Penny grinned, "As good as it sounds to have you balls deep in my ass, all the sheets are in the laundry." I groaned again. "But I ordered another dozen on Morty's card."

I held her close and squeezed her ass.

"You keep that up and this tiny g-string won't stop me from leaving a big wet spot."

I gave her ass a good swat.