The Side Hustle

Since my wife and I have discovered our mutual love of CFNM play and nudity in front of others in general, it has moved our casual clothing optional life into the world of finding those of friends who are like minded to share time with. The circle is small, and each time a new person enters it, it is exciting for both parties.

Which brings us to the topic of our friend Karly. We have known Karly for quite a long time, surely since we moved into this neighborhood and are reasonably close to her. Karly is the master of what they these days call the side hustle. She fully owns and runs an upscale hair and beauty shoppe but also has other things going: In-home wine tasting, chef's products, gourmet chocolate tastings, the list goes on. Her husband Ben is a contract attorney and splits time between NYC where some of his larger clients are and here in New England, but he has been around more lately which makes both of them happier. He feels like his book of business is strong enough to move completely out of NYC (which he hates!) and into this area. They are good people.

Jen recently hired a new associate into her practice which gives her a day off during the week, so when I pulled the car in the garage after school I saw Karly's car in the driveway. Her and Jen were in the living room talking and I changed into some sweats and joined them in a glass of wine.

After some small talk my wife piped up "Karly has a new side gig."

"Oh? What's the next in-house thing?"

"Sex toys and lingerie!!"

I almost spit out my wine. Once I stopped coughing (and they stopped laughing) I was able to say "Sex toys?"

"Yes!" She went on to explain it is a company that sells high quality lingerie (known as Naughty Nighties) as well as couples and solo sex toys. (Mostly) women attend the parties and can try on nighties, feel the sex toys and order them. Karly then delivers them personally. It avoids online ordering or visits to stores which might be uncomfortable. Since Karly also does in home wine tasting she makes it a dual party and follows up the wine tasting with the sex toys. Apparently it has been lucrative.

"How has it been working?"

"So far, so good, the wine tasting loosens everyone up and by the end both businesses do well. I just can't let on to either company that I combine businesses."

"There's more." Jen said

"Oh"

Karly looked at Jen "Are you sure? Jen nodded. Karly took a breath. "Jen has told me that you both enjoy, uh, CFNM play?"

I looked at Jen "Damn, can you at least warn me when people know" I asked in mock annoyance.

"Sorry" she smiled "It just sort of came out when Karly mentioned something I thought might interest you." She walked up to me and sat down "But I should have warned you. Maybe your naughty girl needs a little spanking later."

"Okay you two, that's for later we have business to discuss."

"Please speak."

Karly continued. Our company produces clothing and toys for women but have recently really wanted couples items and things for men. So I just received a new batch of men's products and men's, well I can't really call it lingerie, let's say spicy clothing. Women are hesitant though as they don't know if it will look good on their man, or if he will wear it, and since we don't have the, uh, equipment, if the toys actually worked."

"Okay?"

She went on "I talked to Ben and we were wondering if you and he would be willing to be demonstrators. Part fashion show, part toy party. You would try on some of the undies and then lose them as Jen and I demonstrate how the products work. I gone promise by the end of the evening you will be very happy.

I exhaled "And Ben is okay with this? Like Ben wants to do this? And if you have Ben why do you need me?"

Karly exhaled "I suppose I can let you know, Ben and I also enjoy some naked time alone. Perhaps not as much as you and Jen. And Ben and I adore CFNM time, but we have never brought it out. In fact Jen kind of coaxed it out of me a couple weeks ago. Don't worry! Secret is safe and the party would be most discreet. And since you are wondering there is absolutely positively no man-on-man action or even innuendo. Once I promised Ben he said he was okay with it, and since he was naked at the time I can say he very OK with it. As for why I need you when I have Ben, let's just say there are a number of toys and in case one or the other need a rest to continue, um, performing and testing, that it would be helpful.

I looked to Jen who was nodding approvingly.

"Hmmm."

"What?"

"I guess I am not adverse to this, it sounds fun. But with our professions we can't be known as the kinky doctor and teacher. Also I don't know if Jen told you, but out CFNM is not strictly CF, by the end of the night if I am naked I usually like to see a little something myself."

"Yes, Yes, Jen told me you like your titties. Well let me assuage your fears. First of all the four women at this party will all be women you know. Madonna, Kelly, Monique and Tina. (for reference sake Madonna is a doctor two towns over who Jen and I know from various doctor/representative dinners and Kelly is her receptionist, while Monique and Tina are two women who run a nearby independent bookshop whom we have had some great nights with at town educational fundraisers and political functions.) Secondly they are aware of the private nature of these parties. Third when I told them about ideas I had, without mentioning your names, and knowing your, ahem, requirements, they seemed very open to the idea of baring some, or all as the evening wears on.

"I thought Monique and Kelly were lesbian? What interest would they have in making a naked guy happy?"

"Not lesbian, bi. and while they have been together for 25 years both said it would be nice to see a nice cock or two up close again. I think it everyone will be happy."

"Well honey?" asked Jen. The prospect was intriguing. "Are you good with it? You know I love showing you off and I am comfortable enough, both professionally and privately with trusting these women. I have no problem with showing off a little also. And honey, all four of them, and Kelsey here do have some great racks."

She was right and Kelsey gave a little shake of her boobs accenting that she had no bra on today.

"True" said Kelly "All natural c cups and a trimmed but natural bush." she laughed.

"Fine" I said "You twisted my arm."

"Yay! I will get details out to you. I told Ben that he would see Jen's tits before the night was out" Jen nodded, "And for your hard work I can guarantee that you will see my titties and bush. After that, I suppose it is how well you demonstrate the pieces. And of course if anything gets too out of hand for anyone there is no stupid safe word. Just a "no", or shake of the head and we move on and that goes for everyone.

"Sounds reasonable"

"Okay it will be next weekend at 7:00 and any other info I will let you know." Karly finished up and left and Jen yawned. "We have so much to do here before bed."

"Yes I answered, "Including a spanking for the naughty girl who talks about our private life."

She bit her lip and pouted "Was I really a bad girl"

"Very bad, now lean over the couch and take those pants down. We are going to make your white little bottom a nice rosy pink."

She turned and sexily dropped her shorts and silky panties showing off the ass I love so much. She looked over her shoulder "Please don't hurt me. I didn't mean to be naughty."

I spanked her lightly five times on each cheek and three in the middle as she breathed heavily. "You can get up now." She turned and covered her sex with her hands. "What are you doing naughty girl? I didn't say you could cover up! "I said in mock astonishment. "Naughty girls who do that don't get clothes at all!! Strip!"

Jen pouted and slowly peeled off her clothes. "Please" She whispered. She pressed her naked body against my clothed body "I won't do it again. Please don't spank my pretty pink pussy." She opened her legs, her wet cunt dripping.

"That sounds like a good idea actually." I applied four light swats to her open pussy, letting the last tap slide up, then down slipping a finger in as she moaned.

"Let me show you I can be a good little girl." She slid to her knees and in one swoop drew my pants and underwear off engulfing my cock in her wet mouth. She gagged as she took me deep and I was torn between cumming in her mouth or fucking her tight pussy. I was already turned on and the sight of her mouth alternately filled with my cock or balls made it difficult to think. I reached down to grab her tits and gently pull her hair. I wanted her pussy so bad but then looked up at me with those brown eyes and pulled her mouth off again. "Fuck my face baby, give it good to your nasty, naughty wife."

Damn it she knew what to say. I leaned back as she took me deep swirling her tongue around the ridge of cock. She talked with her mouth full of my dick. "Cum in my mouth baby. Cum for me." She swallowed again and I couldn't hold back as spurt after spurt of cum filled her mouth. She swallowed and said "See I told you I could be a good girl. But damn we need to make you drink some pineapple juice or eat celery or something. Not the best load I ever swallowed." She laughed "You wanna kiss or should I use some mouthwash first?"

"Lots of mouthwash! Do you want another spanking?"

"Really" Her eyes sparkled, and she pursed her lips.

"I turned her around towards the bathroom. "Get that mouth cleaned up" We both laughed and eventually kissed goodnight.

The week passed and we got notice to show up at her house at 5:00 to help with set-up. I spoke with Ben a little and we both agreed that we were the luckiest son of a bitches in the world and that we both were quite nervous. We helped clear off space on couches, set up a modesty screen for changing and even cleared hthe dining room table helping to set up order forms for both companies.

The ladies arrived and soon the four guests, Jen and Kelly were all seated in the living room happily chatting and snacking on the cheese board that was put together. Although Ben and I were fully dressed, and they were all aware that they would probably see something tonight, aside from a few furtive glances up and down there was no mention made of anything.

We helped Kelly pass out wine glasses and she put on a very nice wine tasting. Tilting the glasses to test for tannins, encouraging small sips at first, noting what flavors would be present. Six wines in all (with pouring's that seemed to get bigger as the tasting went on.) a few extra bottles were brought out as were order forms and, tipsy won out as multiple bottles for later delivery were ordered.

After the wine tasting glasses were collected (exchanged for regular stem ware) and cleaned the next thing was to bring in the two chests and the rack with a number of lingerie items and various sizes.

Kelly stood at the front of the room near the fireplace and we all looked around expectantly. "Ok ladies. Thank you all for the wine orders, I hope you found that informative and helped also broaden your knowledge of wines. Now we are moving onto other items of a more risqué nature. I would like to remind all of you, and this is very serious, all of us here have businesses, high profiled businesses and are in places of respect in our community. None of what we are doing here is illegal or immoral. However to some it seems that way. Nudity and sexuality in our country is viewed more negatively that violence and a bare breast will have old ladies clutching their pearls, meanwhile a person blown about by bullets is perfect news fodder."

She looked across the room and continued "As you know my company is my appointment only and all guests are screened so that personal information, who is at the parties and what is purchased are all very private. It is therefore our policy that anything that happens here, who attends and what is purchased, is 100% private. Nothing is held on computer or forms, and all paperwork is promptly shredded and destroyed." She smiled as everyone was nodding and breathing in relief it seemed.

"Now for the fun" she said. "Some of the comments have been that while women can try on lingerie, and feel the toys, there is nothing like having a man see them and comment truthfully. Also many women think their man might look good in something or a toy might be good for them but have no frame of reference. So as you all know both Jen and myself have been happily married for years, We also found out recently that we, as couples, spend more time nude than most and that our wonderful husbands, really enjoy the CFNM lifestyle and don't mind being watched." and after a brief pause "and we don't mind watching them. So the way this evening will work is we will see the ladies lingerie, and you are more than welcome to try them on and show them off for approval. Yes ladies, I have your sizes here. Then the men will model some of our new offering for me and after that we will have sex toys for both males and females. The toys I have here tonight are all available for order, though I do have some on hand. What I have here tonight is donated by the company so we can keep them. It is literally thousands of dollars' worth of toys and clothing. This is a pretty major expenditure for the company, and one that I suggested, so I need to make this work or I will be out some cash. So at the end of the night I will need you all to fill out pretty extensive questionnaires. Sexiness, ease of use, etc. Both you ladies and our two gentlemen. These will be used in future seminars and parties so that we can all have a frame of reference better than what is listed in catalogs. So don't be afraid to try a toy, it will be yours, but there will be chances to order them if you don't get your choice or if you decide you really need it. So without further ado, let's get sexy!"

The nighties and lingerie Karly brought out ranged from the very tasteful seduction styles to the barely there, "slutty line" as she put it. Jen handed items to Karly who explained their quality, their composition (Lace, cotton, silk etc.) and in some cases, special features (Snap crotch, removable cups, dildo attachments.) There were the expected oohs and aahs, but no one moved to try anything on. Finally Karly raised an eye to Jen who grabbed the piece she had. A rather flouncy loose-fitting type short on the bottom in red silk which moved up the body to encase the breasts in a red close-knit fishnet. "God hates a coward" said Jen. Breezily she went behind the modesty screen taking great care to fling her jumpsuit, her bra and finally sexy thong over the top and emerged. The bottom was just short and bouncy enough to allow peeks of pubic hair while the fishnet showed off not just her ample boobs but also her nipples which played peek a boo with the close-knit fishnet. She walked over to me "What do you think baby" and grazed my crotch "Oh You like!" she walked over to Ben "How about you big boy" and did the same "I think we have two thumbs up, or at least something is up"

Monique grabbed Kelly's hand "Too dripping snatches from the bi's in the room!" she shouted as she took another sip of wine and a puff from the joint that had magically appeared.

Jen walked over draping herself across a chair, the bottom again gaping just enough to show the edge of a neatly trimmed muff. "I can't be the only one who wants to try something on" she said

At that Kelly, usually the more reserved of the couple walked up (to Monique's surprise it appears) and grabbed something and disappeared behind the screen. There was much struggling and grunting and cursing behind the screen until she called for Karly who helped her out. Kelly was dressed in an outfit that seemed to have a bow around her pussy and ribbons covering her ass, while her boobs were in a similar get up with a bow covering each nipple. Kelly was always a very conservative dresser, and her clothes often hid her assets. Kelly came out, pirouetted in the room, and slumped down next to Monique smiling almost shyly after the turning around for us. Kelly looked over at Ben and I "Two dicks up again!" Indeed both Ben and I were straining against our clothes. The others did follow trying things on with varying degrees of coverage. Monique went with a very sheer baby doll and even Karly had a classic bra, panties, garter under her clothes. It was Dr. Madonna who shocked everyone with a cupless one piece with snap crotch, her boobs out for all to see. "You forget I am from Italy; we don't have the hang-ups about boobs you Americans do!"

A couple more pieces went on and off and then Karly led Ben and I behind the screen. "Okay gentlemen, out of the clothes... all of them!" We dutifully dripped down to nothing. "Very nice" she said, sizing up our already hard cocks. "You guys could be twins." Truthfully we both were roughly the same size and girth. She handed us each a pair of underwear "Put these on and strut your stuff."

We started with novelty underwear, both full coverage, mine was an elephant front with large hanging snout while Ben's looked like a beagle with a large tongue hanging out. Karly took great joy in grabbing us by the tongue and snout and leading us around while the women cheered. As the outfits went on they got skimpier and skimpier so that our asses were fully exposed and our cocks, hard as they were, and balls were barely contained by the little pouch. The women were also getting more daring, grabbing asses and pouches as Karly professionally (for the most part) explained the clothing and its advantages.

"OK guys, last one, for now" she said. Ben ended up with a fishnet thong that showed everything, while I had a very tight white thong that outlined my hard cock. Ben was shown around first as the women gave his hard member a stroke or a tease. When I was brought up, Karly stated, "This one is tight and shows a great outline but when it gets wet" and with that she unexpectedly threw water on my crotch and instantly the suit was entirely sheer eliciting more cheers. "But we can't have wet underwear on can we?" and she grabbed the tabs on the side which instantly tugged away leaving me totally naked.

"Or dry underwear" called out Jen as she grabbed the side tab on Ben's mesh underwear freeing his hard dick for all.

So there we stood naked with pretty big erections and mostly covered women in lingerie. Karly instantly assessed the situation. "I was going to suggest we start with the female toys, but perhaps we can leave most of those for self-demonstration and we can use our fine studs here to see if this is something you want to take home" she smiled "The toys not the boys!"

She pulled out a bottle of lube "this will be your friend, male or female. use it often and liberally" she said as she pulled out two sleeves. "these are low tech but very effective" You notice each side has an opening that looks like a pussy and that s because they take impressions of porn stars labial lips and use those to build the opening. the rest is a unique series of flexible, squishy silicone nubs. She walked over to her husband and announced the porn stars name he would now be fucking, while Jen did the same for me. To be honest sleeves have never really done it for me, but they still felt pretty good. Jen sensing that I was only mildly aroused started stroking harder and gripping faster which had the desired effect. Ben seemed really into it though and both ladies stopped the stroking to have us take over on ourselves to show it can used as couples and alone. Soon the sleeves were taken though, leaving us hard and now very lubed up.

Next came a sleeve with a vibrating action which can be used with stroking but can also be hands free. I noticed as this was slipped on that Madonna and her receptionist had both discarded their lingerie (or pushed to the side and had grabbed a moderate size dildo and a larger vibrator respectively. they seemed so comfortable with it, I tried to make a mental note to ask Jen if they were was anything between them (both are married.) They seemed awfully comfortable, but that thought was pushed to the back as Jen turned up the vibe action which was resting right below my cock head. "Oh does my hard naked honey like that?" she purred "All naked in front of people we know, and they are watching you grunt and groan?" She took her hand off the sleeve and pinched one nipple than the other. "Oh I should see if Karly has nipple vibrators. think of that, all these clothed women and you with a vibrating cock sleeve and nipple stimulators" She laughed and tried to discreetly rub her pussy.

"Sounds like you like it too!" I groaned

"Mm hmm. I do love seeing my man all frustrated " she then leaned in and whispered, "They want you too I bet, but I get to take you home!"

"And all done" yelled Karly not a moment too soon, leaving me breathless.

"We need to let these men catch their breath. So lets just do one small thing." She held a round latex ring, with a smaller latex ring inside "So ladies, how many of you are familiar with these. These are not your Mother's cock rings" she said to laughs.

"The old metal rings were uncomfortable and difficult to work with. These" She showed the stretchy material "are much safer and more comfortable." She tossed one to Jen and Karly took on for Ben. Jen stretched the bottom over my balls and the inside ring over my cock. Almost instantly the my dick started taking a reddish hue while my balls were jutting out obscenely in front of me. "I love the way it brings the balls up front" and at Karly ran her long red fingernails over Ben's balls which we tight in the ring and elicited a low growl from from him. Jen did the same to me and of course the sensitivity of having your balls bound up also got a low moan from me. "If your man cums quick, which doesn't seem to be an issue with these two, this can help. If you just like the look and the increased sensitivity for foreplay these are fun also. Like with anything though, you should not wear these for hours, but for short times they are fine. After she and Jen gave each of us a a little more teasing and the ladies actually came up to poke around and caress, and in Kelly's case, a few extra strokes and playing more with the balls before she gave a sheepish grin and moved away despite being encouraged by Jen and Kelly to "Use us." Jen and Karly removed the rings, showing how easy it was gave us a chance to retreat to the couch to recover. Once seated she held up something resembling a snail. "What if I told this little item could rock your world, who would like to try?"

Monique raised her hands "I will give it a try". She looked around. I noticed her lingerie from before had shifted giving me a clear view of titties and her neatly trimmed pussy. As if reading my mind she covered her cunt self consciously. "I just think I might be uncomfortable."

Before anyone could answer Karly stepped in "Monique the whole idea of this is fun. Obviously our boys like being the center of attention, but if you don't want to you can go behind the screen or just cover up a little with a blanket.:

She smiled sheepishly. "I'd kinda like Kelly to watch, and I guess the girls deserve a blow by blow. Let's start with the blanket, once I get going I probably won't care who sees my cunt."

Karly found a small blanket and Monique took off her top and dropped the bottom part of her lingerie giving us another look at her neatly trimmed pussy and arranged herself on the floor. This toy vibrated against her pussy and clit, and she must have been super aroused as she was asking for more. Sure enough the towel was shoved aside as her pink pussy devoured the snail until it was mashed against her clit. Her nipples got super erect, and her pussy started leaking out the sides making me think she was squirting and her eyes rolled back in her head. I am not sure I have ever seen a more intense orgasm. Suddenly she quickly took it out "Oh my God, oh fuck, Holy shit holy shit" she breathed out. "I'll take twenty of these" she joked. She took a minute more to come down and looked at Kelly and smiled "I don't need you anymore honey"

Kelly smiled, leaned down and licked her slit "Well who is going to clean up for you."

Monique lifted her face and kissed her back taking her tongue and her juices in her mouth. "Okay, I'll keep your around." Suddenly she looked around at the ladies who were all a little slack jawed (and with hands in their panties) and at Ben and I sporting huge erections. "Oh well, you've seen it all now, no need to cover up anymore I guess."

"Well" said Carly "I know all you girls know about the rabbit, and now about the snail. You have seen the dildoes and vibrators, but one thing I don't think you all have seen is this." She held up a rather moderate sized butt plug looking item with what appeared to be a latex type of cock ring with seeming extra material, almost like a small shelf on it. "This will be the last thing our models will try to tonight. " She looked at Ben and I "This will make you cum, rather quickly I think." Ben and I exchanged glances "Ladies if you enjoy watching that moment you may want to choose a toy. You can cover up if you want or give the boys some visual stimulation. As always, whatever you are comfortable with." With that Karly made good on her promise removing her top, and her panties as my wife discarded her lingerie. If the two of us could have gotten harder it would have been a miracle. Karly's body was fantastic but Jen's hand running down my back and her boobs in my face brought me back from the lesbian fantasy playing in my mind.

Jen and Karly had us like back on our respective couches and lube was applied to the toy and and I felt Jen's finger slowly push up and in. After the first knuckle she pulled out and for a few minutes lightly worked my ass open, careful not to hurt. Once she got three fingers in and Karly had done the same I felt the butt plug moving in and opening my ass up even more "The key ladies to go slow, sex should be all about pleasure" The plug finally reached its point and underneath Jen was able to loop the ring around my blood engorged cock. "These are really stretchy ladies, and the cock should rest a little on this little extra piece of material." She then picked up a small remote. "This turns the little device on and off in two speeds. This can be used in solo play, but just judging from what we have here I would certainly recommend someone there be someone to loosen things up. But as you can see both of are men here have nice full asses. From my vantage point I could see the various ladies were certainly aroused, either caressing their own tits or rubbing toys in there pussies, I know Jen as very aroused as I could smell her sex from my vantage point and since she had removed her clothing I could see the dew like moisture on her hair. "Now when I turn this on, it says the man will come quick. " Being as aroused as I was I didn't doubt that but I wasn't prepared for it. The butt plug vibrated, and had a thrusting end, while the little shelf also moved up and down vibrating. It was like being pegged and getting an amazing hand job at the same time. It didn't take long between the moans of the women watching, my own moans and the fact that Jen had placed her tits in my mouth that I came hard, I actually saw spots. My stomach and the side of Jen's boobs were covered in cum and Karly and Ben were in a similar state. Jen waited a moment and removed the butt plug leaving my ass feeling empty and like usual I felt, at that moment, very exposed but managed to keep my hands from covering up. Of the ladies, they may have felt similar as they were covering up, grabbing their original panties and bras except for Madonna who had a bright red orgasm flush around her chest and she seemed to be just enjoying the afterglow and Jen and Karly.

"Would you guys mind staying naked for a little bit" asked Karly, "No biggie if you can't, I jus though it might be nice to have something to look at while we fill out these questionnaires. Having gotten over my immediate feeling of exposure I was fine, though the sexual aspect of CFNM was kinda over since I spewed about a gallon of cum, or at least it felt like that. Though that didn't stop Jen from touching and caressing my cock or me touching her tits to bring them to little hard points.

Karly got a lot of feedback (we saw it few months afterwards on their website that described a "test with volunteers" and every item that was tried on or used was reviewed, including one or two I sadly missed in my own arousal. Apparently her higher ups were very pleased with both the sales and reviews as she was promoted not long after.)

We went into Monique and Tina's store a few weeks later and they stated we both seemed so overdressed. We laughed and they thought another party, this time with the lingerie and toys that we were gifted or bought (Karly sold a lot that night!!!!) would be fun. "Maybe this time we arrive in lingerie, just to speed things up" said Tina. I 100% agreed though I wondered if I would be wearing the see through or the elephant trunk. The look in Jen's eyes told me she already had ideas.