In for a Penny

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Tease."

I got a good grip on that ass and steered her out the door and to the elevator.

"Now you're just making my nipples ache."

They got pinched and played with on the ride down, and Penny was a bit flushed. She undid one more button on the way over. One more than what was 'appropriate', but it gave me a nice look into her shirt at a lace covered tit.

We pulled up in the driveway and amazingly there was an open space right where it could be seen out the front window. I was going to get out but Penny pulled me to her and laid one hell of a kiss on me. While I was still in a daze I watched her reapply her bright red lipstick, then she took her thumb and wiped what she had left behind on my lips. All I could do was smile. All right, it was an ear to ear fucking grin!

The curtains fell back into place as we got out of the car.

We walked hand in hand to the door, but I didn't get a chance to knock. Mom pulled it open and gave me a big bear hug. She turned to Penny and hesitated. Penny finished it and stepped to mom for a hug.

"Well come in, come in." mom herded us to the den. There was a big roar as somebody did something on the field. "He's here!" mom had to shout.

Bill turned his head and was probably going to show his ass when he stopped. I barely held back a snicker. I felt the slightest elbow from Penny's arm wrapped through mine.

I was right, in less than a minute the TV was the only noise in the room. My brothers and my sister's husband only had eyes for Penny.

"Guys this is Penny, my new wife." She glowed and gave me a peck on the corner of my mouth. "Penny, this is..." I made the rounds of family and kids. Penny treated them all like royalty. My brother's wives had dressed up a bit for today, but none of them held a candle to my Penny. There was nice, there was pretty, and there was class. Then there was Penny, simply elegant.

We sat back and off to the side a bit on an old love seat. But Penny turned her back just a bit and leaned back into me. I put my arm over her shoulder and hand down on the side of her tit. We cuddled, my brothers were having a hard time concentrating on the game.

Mom at least tried to carry on a conversation, and we passed on 'our story'.

"When I got the text last week, I had to fly out to Vegas. That evening I was sitting down in the lounge killing the evening when this vision walked through the door."

"Stop!" Penny groaned and swatted at me.

"I'd had a really bad day with a really bad boss." Penny continued, then reached down and flexed her fingers like she was grabbing ass. Mom got a bit of fire in her eyes. "We got a notice our apartment building was being sold and demolished so we had ninety days to find something. All in all just not good."

Mom shook her head but wanted Penny to continue, otherwise, she would have interrupted with questions.

"Titus was sitting at the bar nursing a drink."

"He always was a lightweight," Bill called out. His wife smacked him. "What?" then turned his attention back to the game.

"We struck up a conversation, I don't even remember about what. Next thing we know it's three in the morning. We said our goodbyes and promised to meet in the morning for breakfast. I don't think I slept a wink."

My sister-in-law snickered.

"So I rush back to the restaurant and there he is, My Prince Charming."

It was my turn to groan. Mom grinned.

"We haven't been apart since. Two days after we met, he asked, and I said yes."

"You mean you screamed yes."

Penny blushed and I got a nice kiss. We just looked at each other. This was not part of the script, but it was... I started to lean back toward her, getting lost in her eyes.

"Ahem!"

I glanced at Mom, then grinned and gave Penny a not so quick peck. Fred made gagging sounds until someone slapped him on the back of the head.

I'm curious, if I kiss Penny again, will he get slapped again?

I was being given the 'mom eye' now, complete with a raised eyebrow. "I do hope you are going to find a better place to live now."

Penny looked at mom, "What's wrong with his place?"

Mom looked at Penny with pity in her eyes, "Oh honey. I know love can blind you, but that dinky little apartment. It's just so..."

I chuckled, Mom and Penny looked at me. I turned to a confused Penny. "Mom still thinks I live up by the college."

"But..." she turned to Mom.

"When did you move honey?"

"Which time?"

Mom went a bit wide eyed, she wanted to ask, but not in front of Penny.

And then Penny did it, oh fuck... You know those time delay circuits they use for live TV to cut something in case someone says something they shouldn't. I really, REALLY, wished I had one right now. "Honey, why don't we have everybody over after I get settled in? What do you say?" She had that twinkle in her eye that should have set off warning bells.

"Sure dear. It will take a few weeks to get everything settled, but sure."

Mom won a battle, so it was time to gloat a little and go for winning the war. Before I knew it, mom was inviting Penny down to see my old room. I had left as much as possible behind when I went off to college.

Downstairs and through the family room, otherwise known as Mom's sewing room, through the partition wall and back around to my old corner. We never got that far, and it still makes me grin.

There was a support pole for the main house beam, and Penny spotted it. She took a few steps towards it, then leaped and spun around on it leaning back as she went around a few times.

"Oh I haven't been on a pole in months. Can we get one honey?"

I was stunned, and mom was coughing.

"It would be so much nicer to have one at home instead of going down to the fitness center to work out."

"Huh?" I asked.

"What, don't they have them out here? All the good facilities in Vegas have pole classes. It's the best workout and it makes you use muscles you don't normally exercise."

I heard choking from behind me and turned to see Gail all red faced. "Well, I guess if it will save you trips to the fitness center we can look at some." I said still facing Gail. She decided to go back upstairs.

Penny jumped up and wrapped her arms around me, she turned to mom, "Isn't he just the best?" then gave me one hell of a kiss. We were alone when we resurfaced. I just wrapped my arm around her and grabbed her ass as we resumed our kiss and grind. She had to wipe my lips and reapply her lipstick again.

We stuck around for another two hours, but there were enough mom interruptions of our kissing and groping that we needed to get home. We didn't make it, well not quite.

We were two blocks away from the house when Penny leaned over and began undoing my pants while trying to caress and squeeze my cock through my slacks. They were pulled open and down a bit along with my shorts. Penny dove in.

She got two not so good strokes, then popped off, flipped the console lid up and out of the way then leaned down and took me to my balls. I was barely keeping it between the lines.

Penny gave me a bit of a break, she just enjoyed sucking and swallowing for a little bit. I had just gotten used to a hot babe sucking me down while driving when she went into overdrive. Throat fucking while driving can make you lose concentration, but I will HIGHLY recommend it.

Penny kicked back pleased with herself and glancing at my cock hanging out. I looked down and grinned at the bright red lipstick ring at the base of my cock. I don't know what Bill would be more jealous of, the fact that she could do it easily, or that she sat there grinning with cum on her chin afterward.

My hands were brought to tits in the elevator, and Penny strutted to the back of the couch and bent over pulling her slacks down as she leaned over. Her thighs were wet.

I dropped my slacks and slid into a wet and willing pussy, a very willing pussy.

"FUCK MY GOD DAMN CUNT!"

I grabbed her hips and just began enjoying her. I also discovered that since she had gotten me off on the trip home, I was in no hurry to blast off in her. Oh yeah, I enjoyed pounding her hard and making her scream in orgasm. Then I'd slow down a little then pick my pace up and listen to her keen before she went off again. I barely held off for her fourth orgasm, but the fifth did me in. Penny was spasming and flailing and speaking in tongues as she came around me. The screech she let out when I filled her pussy should have broken windows for miles around.

I stood there buried in her still quivering pussy, hands braced on her ass as I slowly softened. I stood back as I began to slip from her, and looked down. "That has got to be the fucking hottest thing I have ever seen."

Then the former porn star surprised me. "Take a picture, I want to see."

I pulled my phone out and stepped back one more step to get it all in. Her ass and pussy in the air, her gaping pussy filled with cum and overflowing. I got one pic, then two more as a large dribble ran down her thigh.

I stepped around the other side of the couch and held it down so she could see. Penny moaned and pulled my cum covered cock to her mouth and cleaned me when she looked at pics of her overflowing pussy.

She was still bent over the couch, bare ass in the air. She slowly stroked me as she flipped back and forth between the pics, "Makes me wish we had the place wired for video. I want to see if it looks as hot as it feels."

Then she gasped and looked up at me beet red realizing she had said that out loud.

I smiled, "It looked damn hot from my point of view." And I took a chance, "What would be hotter, watching yourself live, or watching yourself do something from the previous round while I ravage your body?"

Penny was trying not to grin and biting her lip. I reached under to play with her tit and she lifted to give me better access. "So what would it be for you? Watching up between our legs as I plowed your pussy or ass?" that got a hiss before Penny pulled me forward to suck my cock down.

"Or would it be for me? Watching up between my legs as you gorged yourself on my cock? Seeing the expression on your face as you played with your food." Penny groaned. "Mmmmm, and seeing the look on your face when you felt the pulses in my cock as I unload down your throat."

Penny squealed and collapsed down to the couch trying to rip her nipples off as her whole body quivered in orgasm. Her breathing returned close to normal, and she was getting her arms under her.

Well, let's give it a shot. "Stay there, I want to look at you again." She moaned and dropped her face back to the couch. I'll take that as a good sign.

I stepped back behind her and started to firm back up at what I saw. Penny had spread her legs as far as her jeans around her thighs would let her. Her pussy lips were engorged deep red, her juices flowing in a little trickle from her pussy, a healthy mix of hers and my cum. But it had now run down to her jeans and was beginning to soak in.

I lightly ran my fingertip along the edge of one lip. "Oh isn't that fucking hot. Dribbling horny pussy. So wet and horny I could slip right in there, or even put a jumbo dildo in there."

Penny let out a loud moan and quivered a little increasing the flow from her pussy.

"If we had prepared, we could have another hot babe slip her fist in that sloppy pussy while I drove my cock in your ass. Double fucked by fist and cock..."

Penny started spasming and her hips quaking in orgasm. I couldn't take it and let my slacks drop and drove into her pussy almost missing and driving into her ass. Her head came up in a massive scream and she grabbed fistfuls of cushion as I fucked and fucked and fucked.

It was pure cave man fucking of a screaming willing woman. I just grabbed her hips and gave it all I could. Penny was in one long orgasm, and took it up a notch I didn't think possible when I hooked my thumb in her ass for a better grip.

And then she collapsed. I pulled from her still quivering body and ran around the couch to check her. She was still breathing and her pulse was fast but she was okay. Even as I pulled her jeans up and was carrying her to the shower I had to grin. Never made a woman pass out from cumming before!

Undressing a limp woman is not as easy as it sounds. Might not have been too bad if we were on the bed, but in the bathroom, it was a daunting challenge. Even her disheveled look laid back on the toilet was hot. I got a few murmurs as I picked her up and got us into the shower. She came alive long enough to put her arms around my neck, and was barely able to support herself as I dried her off.

I laid her back on the bed, and if I'd had the ability, I would have ravaged her all over again. Laid back, knee kicked out and arms spread. Practically unconscious, and still on display to me.

I pulled the comforter up as I kissed up her body. Baby smooth mound, nipples standing proud, soft neck, and soft lips. Little sounds acknowledging my touch but that was it.

I gathered our clothes, smiling at the crotch of her jeans being TOTALLY soaked. Walking back out to the great room and grinning again. This huge room with twelve foot ceilings and her aroma filled every cubic inch of it.

I made a sandwich and took it out to the balcony and kicked back on the lounger watching the boats on the ocean. Seeing a few of the larger yachts and remembering wishing I had some hot babe out there with them. Smiling knowing I had the hottest babe I could imagine in my bed.

I was just about to the point of having to go in or turn over when Penny came out slowly. She sat in the lounger beside me, but didn't say anything or look at me. FUCK. "Penny, I'm sorry if I took it too far, if I hurt you it wasn't..." that's as far as I got.

Penny launched off her recliner, straddled mine, and laid my barely firm cock up my belly. Then she situated her wet lips on either side and laid on me with her lips on mine going tonsil hunting.

I wrapped my arms around her as she began grinding her lips and clit against me. I let my hands drop a bit and her hips picked up speed. Against my better 'normal' judgment I let my hands drop to her ass and gave it a soft squeeze.

Penny's head came up as she screamed in orgasm then collapsed on me, her hips still trying to work her clit against my now hard cock.

"I'm not sure about earlier inside, but there's a good chance the neighbors heard that one." She just giggled.

We managed to untangle long enough to shift back inside with Penny right back on my lap. I gave her a light kiss, then held her chin so she couldn't look away. "I'm trying to get used to this, I'm just worried that I'll go too far, that somehow you might..."

I got a soft kiss and a grin. "You haven't even come close."

"Even when you passed out?"

Penny was turning red and grinning.

"Okay, but we need a way to know if we've gone too far, either of us."

"How about a safe word?"

I thought a bit, then grinned at the memory of the first time I brought her home. "Anchovies?"

She giggled and nodded her head grinning.

"One down, a hundred million questions to go."

Penny swatted at me then laid her head on my chest. "I'm not that bad."

I kissed her forehead, "No you're sex on legs and every man's dream come true. I'm just afraid of being "a guy" and screwing things up by taking it too far."

"Like?"

"Like the other day in the mall. Walking around with a hot braless babe on my arm is a fantasy I can cross off my list."

"You showing me off was one of mine too," she said softly.

"Glad I could help."

Penny tipped her head up and looked at me, "Does that mean we can't do it again?"

Time to take another chance, "Maybe in a loose knit top that your nipples can poke through?"

I got the lip biting nod I was coming to accept as a definite yes.

"But how far is too far? Sheer tops, sheer dresses, jacking off on your face and strutting you around with cum dripping from your nose and chin?"

Penny reached down between us and began slowly stroking my firming cock, "Would you do that? Would you mark me and show me off like that?"

I looked at her with my mouth hanging open, "Would you really?..."

"I'd drop to my knees in center court and jack you onto my face myself if you told me to. And even knowing it ahead of time I'd still do it."

"I... I..."

"For the right man..." she paused and took a deep breath, "For you," Penny gave me a soft kiss, "I would gladly wear your mark. Put a wide leather collar on me that marks me as yours and I would grin as you buckled it up."

I gulped and got hard, she grinned and wiggled on my hard cock. "For as fucking hot as that sounds, I don't think we could get away with it for very long."

Penny turned and started grinding her wet pussy on my hard cock, "So if you could, how would you mark me as yours? Something that would stand out and still be acceptable." This was said as she brought my hands to her tits and encouraged me to grope and play.

I saw my picture on the wall behind her and grinned. "Bright red lipstick, braless with nipples standing out."

Penny lifted enough to stand my cock up and sink down with a groan, "Too easy. How about a thick chrome ring around my neck?"

Penny was alternating between grinding and fucking herself on my cock. "That would be a bit much. How about you wear a choker all the time?"

One hand came up to her neck before dropping back and picking her pace up. "With a lock on it?"

"Sometimes, or a big thick heart shaped ring. If it was appropriate, a long chain down into your cleavage to draw your eye to those beauties."

Penny was giving herself a good fucking, "A chain... between... my nipples?" she got out between strokes.

I gave the bars in her nipples a slight twist, "I could see that."

Penny collapsed on me, cumming on my cock. I let her slow a little, then grabbed her ass and continued fucking her from underneath. We soaked the couch. I was glad it was washable.

We rolled to the floor still coupled, and I lifted up a bit to see her eyes closed and grinning.

"The next one goes on my tits and face and I want pictures of it. Every time until I get my chokers."

I kissed the tip of her nose. "So should we run right out and get one, or wait a few days?"

Penny covered her face with her hands but was grinning, then rolled us over and sucked my cock clean before dashing to the shower.

I came in as she was finishing, but I wasn't allowed to shower. Well, not myself. I was forced to stand there while Penny lathered me up and made sure every little bit was squeaky clean. She pouted when I insisted on drying us, but after we were dry I pulled her back to me, lifted and squeezed her tits, then rolled a nipple while my finger made a short trip to her pussy. She was just wet enough to slip a finger in and around her clit before bringing it back to my lips to lick it clean. She was also not happy that that was all I was going to do right then.

We cuddled on the bed and discussed her implant and tattoo removal. She was having a love hate decision on the implant removal. She didn't mind getting back down to what she had, but she was worried about being saggy. I kissed her while doing my best to grope and play with her tits to assure her we'd find someone well qualified to do it up right.

Penny was running her finger on the back of my hand that was enjoying her nipple. "Could we um, like make them um, stand out a bit more?" Then she looked at me, "Since you like them that way that is?" the last part coming out in one quick sentence.

"What about what you want?"

There was that lip biting thing again. "Well, I like guys looking, but especially you looking. They stand out okay in thinner tops, but kinda get lost in thicker ones."

I was lightly playing with them, rolling and moving, feeling them stiffen a little. "You know, there will be another problem if you have them sticking out even further."

1...34567...12