Friends Helping Friends Ch. 06

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Christmas shopping with a friend turns interesting.
8.3k words
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Part 6 of the 8 part series

Updated 03/08/2024
Created 08/12/2023
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m_storyman_x
m_storyman_x
10,422 Followers

Thanksgiving was over and Christmas was working it's way closer, with it all the usual things to do. Christmas shopping being included. I'd always struggled on what to get my wife. We kept lists for each other, but her list this year was even shorter than usual. It included three items: sexy dresses, lingerie, and "underwear and stockings that turn you on". Clearly she'd gotten her mind focused on one thing this year. Unfortunately, I wasn't exactly good at picking dresses for her. Lingerie was no problem. Underwear was easy. But dresses? I never did well with those.

We'd agreed that tonight we'd go to the mall and she'd give me some ideas of things she liked. It was bound to help. Mandy was upstairs getting dressed almost half an hour after we were supposed to leave. Why she had to dress up to shop, I don't know, but then I guess it's a woman thing. I was patiently waiting for her to finish getting ready when the doorbell rang. I of course answered it. I could hear Mandy coming down the stairs behind me, her high heels clop clopping with each step as she almost ran down the stairs, clearly trying to beat me to the door. She didn't. I opened the door while she was still a good third of the way up to the second floor, and stood staring at a tall, slender redhead I only vaguely recognized.

"Janice!" Mandy called from behind me.

"Mandy! I made it!" The redhead said cheerfully from where she stood on the front porch.

"You did," my wife answered as the redhead stepped in past me. The two hugged and then separated. "Honey, this is Janice. She's kinda new to the office."

"Hi. I said, feeling confused before looking back at my wife. "Are we still going shopping?" I'd seen my wife dressed up a lot more lately, but the short black zipper dress she had on seemed overkill for shopping. The long-sleeved dress only came to the middle of her thighs and the turtleneck had a zipper that ran down the front from the top of the neck all the way to the hem. The fairly stretchy knit material hugged her curves snuggly, accentuating her full breasts and her curvy hips. I vaguely remember her buying the dress quite a few years ago to wear to a single event, to never come out of the closet again. But here she was, dressed in the sexy black knit material, black stockings that were barely long enough to be covered by the short dress and knee-length leather boots. She looked truly incredible.

My wife laughed softly. "Yes and no. Yes, we're going shopping, but no, not together. I enlisted Janice to help you."

"Help me?"

"I know how hard it is for you to shop for clothes for me, and I really like Janice's style. Since she's almost the exact same size as me, she can help you pick without spoiling the surprise for me!" She turned to look at Janice. "Show him!"

Janice grinned and took off her long coat. She had on a very short red dress that seemed to be little more than a tube of spandex that molded itself to her body, covering everything from just above her nipples to the middle of her thighs, the outfit finished off with red stockings and heels. She was surprisingly close in build to Mandy, right down to her probably 36D breasts. "Wow," was all I could say. "You sure you want me to take her shopping?"

"Why? Afraid you might not be able to keep your hands off me?" Janice said softly as she stepped toward me. She slipped her arms around my waist and leaned her body against mine and ground her pelvis against my already hardening dick. "Glad to see you enjoying the view. It'd be a shame to get all dressed up and not have you enjoy it."

I looked past her toward my wife. She grinned and nodded. "Feel free to tell her how good she looks."

"Well, you do look spectacular." I said a little tentatively, not wanting to piss my wife off at being overly complimentary.

"Thank you!" she said with a smile before her look turned more serious. "Mandy, Jack, I have a question for you two."

"Okay?" I said a little curiously.

"My husband and I play this game when we go clothes shopping so he doesn't get bored. We've talked about trying it with another couple, and since you two are already exploring that kind of thing, maybe you'd be a good couple to share it with."

I was immediately put on guard and answered, "What kind of a game?"

"Well, it's kinda a showing off and flirting kind of game." Janice said, looking back at me, still holding my pelvis against hers, and not seeming to be ready to let go.

"Showing off, like showing off our bodies?" Mandy asked her co-worker.

"That's a pretty close description. Greg gets really turned on watching me flash him and any other guy that happens to be lucky enough to be in the right place at the right time. So, we play a little game, flashing and touching each other while we're shopping."

"Okay. Maybe you better explain more first." I said hesitantly.

"Well, first he buys me a new pair of sexy undies, then we go look at lingerie. I pick at least one thing that I would like to wear for him, and I model it."

"So you put it on for him?" I asked, not sure how this turned into flashing, though I could imagine some pretty skimpy lingerie.

"Uh huh. The rule is, when I model anything, I have to come out of the dressing room completely, and make one full turn for him, before I can go back. If I renege and don't come out, I have to undress in the parking lot and ride home naked. I have to admit, at first it was kinda hard, but now I love it. I get so turned on. Anyway, once we pick a piece of lingerie, and sometimes he makes me try on more than one piece, I put on the panties he bought me. Then we go shopping for dresses. He picks some for me to model, and I pick some I like. Of course the same rules for modeling dresses apply. Anything he picks and asks me to model I have to. The idea is to tease each other to climax before we're done, by both flashing and touching."

"So, like jerking him off or something?" Mandy asked her friend.

"That's one way. Another is to let him get between my thighs or even into me if he can arrange it. My goal is to get him to come in my panties, and his goal is to get me to climax before I get him to come. If he makes me come first, then when we get back to the car, I have to strip and ride him until he fills me. If I get him to come in my panties first, then he has to buy me the lingerie I modeled for him. Easy."

"And all you have to do is, what, get him to jack off in your panties?"

"Well, he can come in my panties with me holding them out, or he can slide it between my thighs, dry humping, some people call it, or he can cum in my pussy and let it leak out into the panties. I mean, we can't exactly go around coming on the floor, can we? It has to end up in the panties."

"That sounds like it could be difficult," Mandy said, looking at me to see my reaction.

"Not as hard as you think, not if you get creative and do things in short little bits. Oh, I almost forgot, I'm not allowed to touch my panties unless his dick is hanging out. So if he pulls them down my thighs to play with my pussy, well they stay down until he pulls them up, or I fish out his dick. Sometimes he'll pull the panties down so far that they almost show below my dress, and I have to leave them there. But the positive side is then that I can lift my dress and flash him my bare pussy, which he absolutely loves."

"And you guys do this a lot?" I asked, a little surprised at the game.

"Almost every time we go shopping." She said with a grin.

"And you never get caught?" Mandy asked.

"Oh, I didn't say that. We get caught by people a lot. The trick is to not get caught with your goodies hanging out. There's not much anyone can do if your husband has his hands under your dress, but you don't wanna get caught even partly naked with kids around! Bad, bad situation. No, you have to be really careful about when and where, but that's part of the stimulation, trying to guess where your partner is going to do something. I've gone so far as to try on a dress and then, standing right in the middle of the dressing room area, slip it off so I'm completely naked before I walked back into the dressing room. Or accidently have a dressing room door come open. One time I hid in the middle of a clothes rack and he leaned on it while I sucked his dick with other people all around us."

"And he likes this?"

"One time, he took me to the shoe department with my panties way down my legs. So far down that my dress didn't even cover them. He had me try on some high heels. I thought the poor boy helping me was going to cream his pants when I asked him to slide my panties back up. Just because I couldn't touch them, didn't mean I couldn't ask a stranger to."

"Did he?" Mandy asked.

"Oh yeah. I even made sure he got two fingers into my pussy before he was done too. That nearly did make Greg cream his pants. I took him behind a rack, and pulled his dick out and in less than a minute I had him coming in my panties."

"So you won and got the lingerie?" Mandy asked.

"Uh, No. The shoe boy made me climax, so I lost. But I didn't care. It was the first time I had anyone other than Greg make me climax in a public place."

"And you want us to play this game?" I asked Janice, looking back at my wife to see that she was clearly interested.

"I think it'd be fun to try with someone besides Greg. What do you say stud? Game to try?"

I looked at Mandy. "You sure you want to do this?"

"Well, it does turn me on a little to walk around without underwear on. Maybe we try it? Just once?"

"Great! Take off your panties and bra." Janice said as she released me and turned to face Mandy.

I watched as my wife unzipped her dress and take it all the way off. She stripped off her bra and panties and put the dress back on. I could see how this dress had lots of potential for flashing, and I could now also see her nipples poking the top of the dress out. I was really wishing I was taking her shopping. I wouldn't at all mind watching her flash me in all kinds of places around a store.

"Alright, Greg is waiting in the car. We'll meet back here at nine-thirty." Janice said to both of us.

"You're not coming?" Mandy asked suddenly.

"With you? No. If Greg wins, well, you'd be the first time he's been with someone else. Might as well let him enjoy it without worrying about me watching. Besides, Jack still needs to get ready."

"I am ready." I protested.

"Not if you're still wearing underwear. How will I get to your dick if you're wearing all those layers?"

"Oh, well, yeah. I can see that." I said a little sheepishly.

Mandy got her coat out of the closet and put it on, covering almost her entire dress. I couldn't help but think that if she wanted to, she could unzip the dress and walk around in just the coat. "Oh, one more thing," Janice said as Mandy got ready to go out the door. "Don't let him forget he's supposed to be buying MY Christmas presents."

"I won't."

"Oh, and yeah, I should probably warn you. He's a bit of an exhibitionist. If he hasn't already pulled his pants down and given himself a hard-on for you to look at, I'd be surprised."

"He'd do that?" Mandy asked with raised eyebrows.

"I'd be surprised if he hasn't. But then, use it to your advantage. If you get him all worked up even before you get to the store, it'll be so much easier to get him to fire off in your panties!"

"Um, okay then. See you in a couple hours hon," Mandy said a little nervously as she stepped out.

"Now, lets get your clothes off," Janice said with a naughty little grin. "At least your pants. I wanna see what I get to work with."

"What you get to work with?"

"Sure. Flashing you, sucking your dick, stroking you, trying to get you into my pussy. Might as well enjoy ourselves. That's the whole point of the game, right?'

"I guess so," I agreed. I walked into the living room and began taking my pants off. It struck me that over the last few months I'd become surprisingly comfortable getting undressed in front of women other than my wife. I pulled my briefs down and off, and stood back straight as she gripped my hips and then slid her hands around my waist. Both hands moved down to my partly hard dick and grasped it.

"Mmmm. Feels like it could be nice. You are going to let me look, aren't you?"

"For a price."

"Let me guess. You want to see me, too?"

"Seems fair."

"Then all you need to do is turn around."

I turned to face her as she released me and stepped back. Her coat was tossed on the floor and the tube type red dress was lying on top of it, leaving her in nothing but her red stockings and heels. Her skin was creamy white, flecked with little reddish freckles all over her body, including her full, rather firm looking, breasts. She had a very small patch of auburn curls on her mound, trimmed into the shape of a heart, the tip pointing down toward her full, round, creamy white lips. She had a small amount of inner labia protruding down between a modest-sized triangular gap where her legs met. "Well?"

"Uh, damn," I mumbled, looking at her incredibly sexy body.

She stepped toward me and reached down for my dick, wrapping one hand around it as it grew to its full proportions. "I could say the same thing," she whispered as she pressed her body against mine, my dick still in one of her hands. She pushed her tits against my chest and then her lips to mine. We stood there, my hands stroking her hips, butt and back, while we shared a long, wet, lip-sucking erotic kiss. "You know, I've never had another man in me since I got married. This would be the first time and I'm a little nervous. Maybe it would be a good idea to try that before we go out?"

"You think that's a good idea? Us having sex I mean?"

"I think if I don't, I'll regret it all night," she whispered. "Just for a minute."

"You sure your husband won't mind?"

"If my husband is half the man I think he is, by now he's found a quiet parking lot to get to know your wife a little better."

"You think they're having sex?"

"I think if she says yes when he asks, that he'll be more than happy to try it. We've talked about doing something like this a long time, but never quite knew how to find a couple to try it with."

"Well, if you're sure."

"I am."

I gently turned her around and pushed her back until she had to sit on the sofa. I knelt down then lifted and spread her legs. "Better get you wet then." I whispered before lowering my face to her pink pussy lips. I slowly licked up her slit, tasting her wetness and teasing just the tips of her lips.

"Oh fuuuuuuck," she moaned softly as I dipped my tongue between her lips on my second long, slow pass. I used my fingers to spread her firm outer lips and flicked the tip of my tongue across her clit. "SHIT!" she gasped in surprise. She reached for my head to grab at my short hair and try to pull me to her as I started to lick faster. I teased my tongue up her slit over and over, tasting her quickly increasing juices, pushing the tip of my tongue between her lips to flick across her clit. She moaned loudly and began to shudder as I concentrated on her hard, sensitive nub, pushing her oncoming orgasm closer and closer to climax. Her legs began to tremble as her moans grew louder as I pushed her further up that wonderful slope.

I could tell by her humping hips and moans that she was close, but I wasn't quite ready to push her over the top yet. I pulled my face away and shifted on my knees between her legs, bringing my engorged head to her wet lips. I pressed my mushroom against her pussy lips and rocked my hips, sliding my cock across her lips. I stroked it that way several times, pushing it down against her with my fingers, putting enough pressure on it to spread her lips and force my rock-hard shaft to rub across her clit. I rocked my hips, stroking the bottom side of my shaft and my engorged head along her sopping wet slit, pushing her orgasm closer and closer to fruition. I watched her body language, and knew she had to be almost there. I put a little more pressure on my dick as I pulled my hips back a little further, settling my head into the entrance to her depths. Part of me wanted to just thrust it into her, but I held myself back and slowly, very very slowly, pushed my engorged shaft and head into her.

"OHHHHHHH FUUUUUCK!" she cried as she felt me forcing my member into her surprisingly tight little tunnel. "OH GOD DAMN YES!" she cried as her climax overtook her body. Once I felt her pussy clench around me in climax, I started pumping my dick in and out of her with abandon, pushing her climax higher by the second, her whole body shaking and spasming as her pussy contracted around my shaft. I knew I was going to come any second, and I suspected she didn't want me filling her pussy, at least not yet. I pulled out of her and pressed my shaft to her pussy with my fingers again, continuing to stroke my cock along her wet slit, teasing the underside of my engorged head with her lips and clit until I could hold back no longer.

"Uhhh, damn," I grunted as my body bucked toward her. My cock spurted a huge streamer of cum out at her as my balls pressed against her leaking pussy, the streamer landing on her face it sailed so far. The second and third landed on her firm, round tits and the fourth and fifth on her stomach. I stood there, panting, looking at her incredibly sexy body as my dick oozed the remaining cum onto her mound and her auburn curls.

"Oh fuck," she panted.

"Sorry about that."

She giggled. "Sorry? You're kidding, right? When Mandy said you were fifty-four, I was like, oh man, this isn't going to be all that good, but shit, you don't look fifty-four and you sure as hell don't fuck like it!"

"Thanks, I guess."

She pushed me back and got up. She walked to the kitchen and found a dish towel then used it to wipe my cum off of herself. She came back with a smile. "Let's try not to do that in the store. I'm a bit of an exhibitionist, but I don't know if I could walk through a store with cum all over my face."

"Yeah. I won't." I agreed with a nod. I started pulling my pants back on as she stepped into her tube dress and pulled it up. Her coat came next and she was dressed far faster than I could be.

The mall wasn't too far away, only about twenty minutes from our house. I parked near the entrance that I knew was close to Victoria's secret, even though I didn't visit it very often any longer. I used to frequent it often, that and a little independent lingerie shop further down the mall buying things for my wife. But that was before I'd given up on giving my wife lingerie she never wanted to wear. It felt a bit odd walking into the mall with Janice on my arm instead of my wife, but then, most of the looks we were suddenly getting, were probably due to her being much younger than I was, or maybe it was just how hot she looked. It was pretty clear to anyone looking that I wasn't her father, but I was actually old enough to be! I let her lead me to Victoria, and then a large display of underwear.

"Pick something revealing and stringy," she whispered.

"Stringy?"

"Yeah, you know, strings, like a thong. It'll show less when I walk around with 'em pulled halfway down." She giggled.

I chose a see-through cream colored thong, which she didn't bother to try on. I paid for it at the counter, the young woman behind the register giving me a disapproving look. I supposed she thought Janice was a kept woman and I was her sugar daddy. Anyway, we walked out and then Janice led us down to that same little lingerie shop I'd stopped in so often years ago. I was a little surprised it was still there. "Pick anything you desire, and I'll model it for you," she whispered in my ear, her hand finding my crotch and stroking my dick through my pants.

"Even if it shows a lot?"

"ESPECIALLY if it shows a lot!" She giggled. "When I married Greg I wasn't nearly as much of a show off as I am now, but it kinda grew on me, so enjoy it!"

m_storyman_x
m_storyman_x
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