Lost in His Past

"I have to wear it naked?"

"Uh huh. I am." She answered with a giggle, lifting the tiny skirt front up far enough for him to see her shaved pussy. "Now if you hurry and get undressed I might be inclined to play a little before we have to go."

"Play like in how?" He asked as he pulled his shirt up and off.

"You can do anything you want to me as long as you don't take anything I'm wearing off. Of course you have to have your costume on as well and you can't take anything off from that either." She said as she spread her legs apart slightly, letting one finger slide down between her legs. "And I've been thinking about this for hours, so you can imagine how wet I am right now."

"Good lord. What have I gotten myself into?" William asked quietly as he stripped off the rest of his clothes, leaving him standing there completely naked with a raging hardon pointing at her. "So do I get to see what I'm wearing or do you just want me to fuck you right now?"

"Well, since you're offering!" she answered with a grin. She stood up, pulled the skirt up as far as it would go, exposing the tops of her thigh high stockings and her completely bare ass and pussy. She sat back down and lifted her legs high in the air, spreading them in a wide V to give him a perfect view of her pussy. "I'll take one big fat hard cock please. You do deliver, don't you?"

William may have had concerns and doubts about being with a woman half his age, but he was still a man, and having a bare naked pussy thrust at him with an invitation to fuck wasn't something he could pass up. He stepped to her, his hard cock sticking toward her face between her legs as he reached up and caressed her thighs softly through the mesh stockings.

"Ohhhh that does feel nice. I thought you might wanna just shove it deep in me right away."

"In a minute," He answered, letting his cock rest on her exposed pussy. He continued to stroke what was left exposed of her legs above her boots while he gently stroked his cock across her exposed pussy.

"Oh god what a tease!" she moaned loudly as she reached between her own legs and pressed his cock harder against her lips and clit. "Ohhhhh yeah what a tease."

"You like being teased?" William asked her quietly.

"Uh huh. But I also like feeling your cock inside me. I so wanted to just push you down and ride you this afternoon. If my sons hadn't been there I'd have let you take me in the pool, on the table, in a chair or even hanging on the jungle gym. Sweetie I'd have let you put this fantastic cock into me anyplace....oh damn!" she moaned as he pulled back far enough to let his cock slide down her lips and press between them, his fat head pushing into her tunnel. "Oh god yes. You could have done this anyplace you wanted."

He worked his cock in and out in short little strokes, each only an inch or two long, but each one pushing slightly deeper than the last. With his whole length finally lubricated he started stroking into her, pulling out until only his head remained inside, then pushing quickly into her again.

"Ohhhh fuck fuck fuck!" she cried loudly as he drove into her over and over again. "God you fill me so much. I don't think I've ever been so completely fucked as you do to me!"

"You feel pretty fucking good around me too," he grunted as he pushed in and out of her pussy, her tight walls gripping him and caressing his shaft as he drove in until his head bumped against her cervix.

"God you're going to make me come!" she squealed loudly, her feet dropping to the edge of the bed to lift her hips in time with his thrusts. She moved both hands to her breasts, sliding the gloved hands in between the satin cups of the outfit and her own bare nipples. "God god god god it feel s so good!" she cried a bit louder. "Fill me up. Oh fuck fill me. Fuck my hot little pussy. Ram it in me. I wanna feel you drive it all the way in meeeee!" she squealed, her voice easily an octave higher than her normal tone. "AHHHHHH FUCK I'm COMING!" she screamed loudly as he slammed his cock into her over and over, his thighs slapping loudly against her bare ass as she rocked up to meet his powerful thrusts.

"Oh shit yes!" William groaned as she orgasmed around his cock, her pulsating pussy pushing his own climax to its limit. His body jerked, jamming his cock deep into her and unleashing a huge gush of cum into her. "Oh damn." He panted as his body jerked time after time, pumping more cum into her with each passing second.

"Oh baby that was perfect," she cooed as she lay there on his bed, his cock still twitching inside her. "I've wanted to feel that all afternoon."

"Glad you enjoyed it. I know I damn well did." William panted, trying to catch his breath and allow his body to recover from the adrenalin that has been surging through his veins.

"Ok stud, now get that costume on so we can go have some more fun." She said, pushing him back gently. As his fat cock pulled from her a gush of their combined juices leaked from her gaping pussy onto the bed. "Goodness I feel like the floodgates opened." She giggled as William walked to the bathroom, coming back with a wad of toilet paper.

She took the paper and covered her pussy as she got up, walking comically bow legged to the bathroom.

William chuckled to himself as he unzipped the bag. The outfit looked like a dark reddish leather wrap around skirt with a wide brown leather belt, and a cape of similarly dark red material. "What is this? A dress?"

"Not at all lover, You're a Spartan warrior." She said leaning against the bathroom doorway.

"I'm really supposed to wear this?"

"Too exposed? No more than me." She said with a giggle, walking over toward him and running her hands around his sides from behind until her body was pressed against his naked skin. "You'll wear it for me, wont you?"

"I've never worn a dress before."

"But just think how well I can tease you at the party. Just slide my hand up under and squeeze your big cock!" she cooed softly as she let one hand slide down and wrap around his deflated cock. "Not to mention that I'm as exposed as you are. Just think. You can slip your hand between my legs any time you want and play with my wet pussy. Does that excite you? Knowing that I'm gonna be completely exposed for you?"

"Actually it does." He answered honestly. "Where do you get these naughty little ideas?"

"Oh that's easy. I thought about all the things my ex wanted me to do or try and figured that if I ever met someone else that I really really liked I'd do my best to do them all for him." She answered, giving him a tight squeeze from behind. "And I really really really like you." She finished in a whisper.

"Even if I'm twice your age?"

"You know, when I first saw you I didn't even consider you a prospect. Way too old for me. But one night I had this really weird and convoluted dream about getting old all alone and decided that age really didn't matter nearly as much as attraction and love. I wouldn't say I love you, way too early for me to even think that way, but I will say, I am incredibly attracted to you. Sometimes I lay in bed and can't get you out of my mind and then have these really realistic dreams about you. Yeah, I'm definitely attracted."

"So it would seem." William answered, not quite sure how to reply. He was incredibly attracted to her too, and not just because of the great sex, but when he was with her, touching her, looking at her, a big part of that hole inside him didn't feel quite so large and intimidating. To some extent she warmed his heart in a way that only his late wife had. He couldn't explain it or understand it, and at some level it bothered him, but the effect was none the less there.

"Come on now. Let's get you dressed so we can go before all the good food is gone!" she said as she released him and stepped back.

"I still don't know about this." He said as he pulled the leather skirt out and stepped into it.

With a little help from Shelly he was soon dressed in the skirt and cape, only part of his chest bare as the cape hung over one shoulder, a large metal buckle holding it closed around his neck at his left shoulder. The sandals were another issue all together. If not for Shelly he felt like he'd be going barefooted, unable to quite get the twisting around the leg ties done right. He followed her down the stairs and out to her car, where he climbed in the passenger side.

"You know," she said as she pulled out of the driveway, "with both my hands on the steering wheel I really couldn't do anything to stop you if you decided to play with my pussy."

"Oh really?" William asked in reply as she put the car in gear and headed down the street. "What if I did something like this?" He asked as he reached up to her shoulder and undid one of the snaps that held the leather strap in one of the brass rings that held her top in place. He flicked the second snap loose, allowing that strap also to slip from the ring, leaving nothing holding the costumes black and gold cup up. The weight of her big breast pushed the cup down and he quickly peeled it down further, leaving her whole breast exposed and hanging out the front of the costume.

"Nope, can't do anything about that either." She answered with a smile. "But I will tell you this, if you tease me you better be ready to satisfy me later!"

"If you mean satisfy by allowing you to pretend I'm your sturdy steed, I'm game. I'd love to see you straddling me in that outfit bouncing up and down like you were riding across country."

"I'm more than game for that." She said in a soft whisper, "especially if you keep teasing my tits like that." She added as he gently ran his finger back and forth across her soft breast and rock hard nipple.

"So you like that, do you?"

"Very much. The only thing better is when you do that with your tongue."

"Hmmm not sure I can do that here, but we'll see when I might be able to sneak in a lick or two." He said with a grin, continuing to stroke his finger slowly across her hard nipple.

By the time they pulled into the parking area of where she worked, a large industrial looking building with a name he didn't recognize on the front, Shelly was more than ready for him to continue his attentions elsewhere, a fact that she made known more than once on the drive, and a fact which William had intentionally ignored.

William got out of the car and walked around to open the door for Shelly. She climbed out, making sure she spread her legs wide so her pussy would be visible in the parking lot lights before she stood up. Once up out of the car she wrapped her hands around his neck and pulled his face to hers, her lips sucking his, and her tongue trying to force its way aggressively into his mouth.

"God you've got me so damn horny!" she whispered. "I wouldn't mind getting fucked right here again."

"Here? In the middle of the parking lot?" He asked in surprise.

"Fuck yeah. Right here right now." She practically demanded as she pulled them to the hood and lifted herself on the fender. She wrapped her legs around his and pulled him to her so his growing hardon would press between her legs against her wet pussy. "I don't know why, something about you screams at me to throw all caution to the wind. Take me. Just take me right here and fuck my brains out!" she begged huskily, one hand slipping from around his neck to reach down and pull his costume up enough to free his cock.

"Seriously?"

"Uh huh. Fuck me baby! Please!?" She begged as she rubbed his cockhead up and down between her wet lips.

"Shelly!"

"Uh huh. That's me. Come on. Stop teasing and make me come!" She begged, the bright moonlight and the bright parking lot lights making the scene anything but private. "No one can tell who we are. We have masks on. Come on, fuck me." She continued to beg.

In answer he pushed his hips toward her, sliding his fat cock into her with a soft squishing sound from her pussy and a moan from her lips.

"Oh yeah. That's it. Kiss me and fuck me." She begged, trying to pull his face down to hers. He let her press her lips to his and then began to stroke in and out of her pussy, one hand balancing him on the car fender and the other reaching for her still exposed tit. He squeezed and kneaded her breast as he pumped his cock in and out of her pussy, her moans, muffled by his own mouth, grew more insistent by the moment.

"Oh yes baby. Right there....god just like that!" she squeaked softly, breaking the kiss but still pressing her forehead to his. "God you're gonna do it. Gonna make me come just with your fantastic.....oh fuck me!" she squealed loudly as her whole body shuddered. She let go of his neck and leaned back, her arms and legs shaking as her pussy convulsed around him. He felt her vaginal muscles rippling along his cock, trying to pull his fat shaft deeper and deeper.

He continued to slowly stroke in and out of her as her orgasm passed slowly away, her shuddering slowing and her trembling legs once again still.

"God damn that was intense." She panted. "But you didn't come!"

"I will. I'm saving it for that ride you promised."

"Oh sweetie, I'll ride you any time any place. You just name it."

"Later my horny little bandita." He answered, reaching both hands up to fix her costume cup and snap the leather straps back in place. He pulled from her, his cock pulling free with a loud slurp. He pushed his skirt down to try and cover his erection and finally gave up. "I can't go in there like this."

"Hmmmm no you can't. But you can put it back inside me and finish off inside me."

"you'd be leaking all over for the next hour. No, we'll just wait a few minutes. It'll go down."

"Too bad. I kind of like the look. Definitely matches the outfit. I know guys that would kill to show off a bulge like that."

"Really? Seems kind of embarrassing to me."

"Come on." She said, sliding off the hood. "Time to go. And if you're still showing when we get in there, all the better for me." She slipped her arm into his and guided them both around the parked cars toward the doors of a large building. As soon as they were opened the sounds and scents of the party closed around them. People of all sizes, shape and of course both sexes took the opportunity to dress in everything from ridiculous outfits to very suggestive and revealing outfits. If he expected his hardon to go down after he got in here he realized he was quite mistaken, especially when a maid walked by, the thin lace bra failing to hide her nipples and the short lace skirt and tiny white apron allowing anyone who wanted to, to see that her black thong panties were as much around her thighs as they were covering her. William wondered if she knew how much she was exposing, but got his answer as she reached a staircase heading to what looked like some upstairs offices. She stepped up several stairs, stopped, and pushed the panties down the rest of the way before continuing on up the stairs.

A young man in a fireman's costume quickly picked up the panties she left on the stairs and followed her up, disappearing down the hall.

"Well, Angelina got her wish." Shelly said quietly.

"What wish was that?"

"She said if she couldn't get fucked tonight that there was no hope she'd ever feel a man's cock inside her again."

"Wouldn't seem like she'd have a hard time finding a guy to fuck her with looks like that."

"Wouldn't be, except that she has a reputation for being a lesbian. It's not true of course, but her last boyfriend started the rumor that she was and that's why they broke up. The real reason is that he has a tiny little prick and couldn't satisfy her with it." Shelly said with a giggle.

"geez."

"Oh yeah. And then there's Jenifer." She said pointing toward a woman in a Greek goddess outfit. "I'll bet you dimes for doughnuts that she's as naked under that as I am under this."

"Why would it matter?"

"Cuz she wants to get Mister Jenkins, her boss, alone and try and get him to fuck her. She's been trying all year to get him into her. I'm sure she pulled out all the stops tonight."

"So why doesn't he?"

"See that tall woman in the old fashioned dress? That's his wife."

"Ohhhh, I see." He answered as she steered him across the room. They stopped by a small potted tree along the wall and she wrapped an arm around his neck and pulled him down to kiss him.

"What was that for?"

"Just to mark you. I didn't want anyone stealing you away before I could come back."

"Back from where?"

"Well, to be honest, I gotta pee. Side effect of the sex." She whispered.

"Oh, okay. I'll wait here."

"Good boy. Don't fuck anything I wouldn't ," she said before disappearing into the crowd.

William stood against the wall, watching the wide array of costumed people go by. Some were downright scandalous in what they failed to cover, but the majority were either much more subtle or simply more conservative. As he was standing there he saw a woman in a snow white toga walk toward him. In many ways she reminded him of his late wife, similar build, full round breasts, but not too big, long blond hair. Yeah she could have easily been his wife thirty years ago, but then back then you didn't wear anything that revealing.

As she approached he knew that under the thin white costume her tits were free, each one wiggling and bouncing slightly as she approached.

"Hello William." She said quietly as she stepped up to him, wrapping one arm around his neck. Her other hand quickly moved to his cock hidden under the skirt portion of his uniform.

"You know me?" He asked, reaching for her hand to pull it away from where it had closed around his cock.

"I do. I know everything about you. But then you know almost as much about me as well."

"I do?" William asked in confusion. Yes she had a mask on that blocked the whole upper half of her face, but even if she hadn't been wearing the mask he wasn't at all sure where he could have met her. "I'm sorry, I don't."

"Tell me William, what do you see in that girl?"

"Huh?"

"Simple enough question, what do you see in her? She's very young for you. Only half your age. Isn't that a bit young?"

"I suppose it could be, but she says age doesn't matter. I would have argued that point until a few hours ago....what do you mean she's only half my age? How would you know?"

"I know a lot of things, but I still want you to tell me what happened a few hours ago. Certainly it was more than just some good sex?"

"No, actually we just sat on the patio and talked. We actually have a lot in common."

"You have much more in common than you know. Tell me William, what would your wife think about you getting involved with someone again?"

"My wife?" he asked back, his face slipping from the happy smile he as he thought about his late wife. "I'm not sure she'd approve, especially someone half my age."

"I think she'd approve of anyone that you loved, truly loved. Just because she was taken to heaven doesn't mean you should stop living life."

"I don't know that she would agree."

"Oh William, I would have thought you would have known me better than that by now." She practically whispered.

"I don't even know your name, how can I know you?"

"Mary. My name is Mary. Does that help?"

"Not really."

"Trust me, it will. But let's get back to Shelly. Do you love her?"

"I don't know. I kind of feel like I could. I know I'm strongly attracted to her."

"I know that too. I've seen how you look at her, how she looks at you. Yes, you two could make a good couple."

"Well, thank you Mary. But I don't know. My wife hasn't been gone all that long and to be honest I feel a bit like I'm somehow cheating on my wife."

"Trust me you're not. And if you like this woman, really like her, then do what you need to do to see if it's love. Age really doesn't matter after all." She said as she leaned closer and pressed her lips to his. It was a soft kiss, a loving kiss, and to William it felt every bit the same as the last few kisses his wife had given him. He suddenly missed her very much and wondered just what he was doing here anyway.