The Extra Person Wingman

Sequel to:

"The Extra Person: Watching, Helping (Literotica, Jan 2022)"

"The Extra Person: Playing (Literotica, April 2023)"

* * * * * * * * * *

Kate turned on the shower, stripped down to nothing, and stood in front of the mirror. It was still almost four hours until Tonya and Eric picked her up for a day at GrapeFest, but she was already so excited it was difficult to sit still. After going many years where her only sexual relief was courtesy of her imagination and her finger or vibrator, she had finally hooked up with her friend and his wife for an exciting night of voyeurism and sexual release (The Extra Person: Watching, Helping, Literotica, Jan 2022).

That night had included many firsts for her - her first time watching others having sex, her first time since before her marriage having sex with someone other than her husband, her first time with a woman, her first time having sex with multiple partners... And then her new friend Tonya promised she could get her laid again - another new notch in her headboard to help her celebrate being a grown, sexual, independent woman. The more she remembered that night less than a week ago, the hornier she got (The Extra Person: Playing, Literotica, April 2023).

She took one last look in the mirror - her curly blond hair, hourglass figure, neatly-trimmed light-brown pubic hair, recent pedicure - and remembered Tonya telling her how sexy she was before diving between her legs. She hoped Tonya's boast that she could get her laid any time was true, but if not her Plan B was another night with them - either way, she was having sex that night. Still, a little warm up wouldn't hurt anything.

She stepped in the warm water and and felt renewed excitement as she applied soap. When she applied it to her boobs, she could close her eyes and remember Tonya's soft, full lips sucking her nipples. When she applied it between her legs, she remembered Eric filling her with his erection, her first fuck in way too many years. As she applied the soap, fantasized about her friends, and transitioned from cleanliness to physical pleasure, her biggest decisions were rubbing her clit or fingering her pussy, and what new fantasy to use as she gave herself another amazing orgasm.

She had developed many new fantasies during their encounter, and each one had delivered deep, intense, fulfilling orgasms. It helped that she hadn't missed a day since. She had relived each memory of them, and was even exploring new possibilities for their next time. Most of her masturbatory sessions were in bed, either while she was trying to go to sleep, or when she woke up after an intense, sexual dream, but she had done one in her car and one in the laundry room when she washed the panties that both Tonya and Eric had used to smell her womanhood last weekend.

This was her first time in the shower, and as she slid a soapy finger in to her wet, soapy pussy, she imagined she wasn't alone in the shower, and it was Tonya's finger giving her the pleasure. As she started feeling it in more of her body, Tonya's finger was replaced by Eric's erection, and as he fucked her Tonya sucked her nipples. In her fantasy, she was watching both of them giving her pleasure in the shower, and she felt the unmistakable tingling deep inside her body that quickly turned to pleasure waves coursing through her body. In just seconds, her short, blissful trip to another amazing orgasm was complete.

* * * * * * * * * *

The orgasmic spasms spreading through Tonya's body slowed as she removed her soapy fingers from between her legs. As the image of licking her own pussy juices from Kate's face subsided she opened her eyes and saw Eric hungrily smiling.

"Oh CRAP, how long have you been there?" she asked a little embarrassed. Even though she often masturbated in front of him, it was still a surprise when it wasn't a planned occurrence.

"Long enough to really enjoy the show!" he said with a huge smile.

"Oh stop," she said. "You've seen me do that plenty of times," she added as she dried off.

"Yeah, but usually after I asked you to. It's very different to see you doing it in the wild. Thinking about today?"

"Yeah, and I can't decide what I want to happen. Part of me wants to hook her up with someone so I can enjoy my voyeuristic side again, but part of me wants to not hook her up so we can be with her again."

"Yeah, that's a great conundrum to have - either outcome is amazing..." her horny husband answered.

"You're OK with doing this?" Tonya asked as she found a matching panties and bra that she wouldn't mind someone seeing later.

"Yeah, definitely - we've been fucking like newlyweds this week - I can't see that changing no matter what happens today. I would LOVE to rub one out myself, but I can't. I'm not as young as I used to be, and if for some reason we hook up with Kate again, I need all my energy for the two of you. If I do anything now, I may not be able later tonight." Eric looked pleased at his dilemma.

"Oh, poor baby - can't jack off because he has to be ready to fuck two women. I bet there are so many guys who would like to have that problem!"

Eric watched her put on the bra and panties almost wishing she was instead taking them off for them the have hot, steamy sex. It was a great problem to have - either jack off while fantasizing about two women, ravishing one of those women right now, or waiting a few hours and possibly getting to be with the two women from his first option - it was a great problem!

"I can't sit here and watch you get dressed - it makes me too horny. I'm going to go put ice cubes down my pants to see if I can get this thing under control."

"Fine, Sweetheart," Tonya replied, laughing. "Just don't do anything to damage it - it will be used later!"

* * * * * * * * * *

Eric and Tonya were a few minutes early when they arrived to pick Kate up for GrapeFest. Tonya, normally fussing with her hair as Eric was trying to get her in the car, was excited about her new wingman role and was ready early for the first time in many years. She was dressed, gorgeous, and ready to try to get Kate laid. If her plan worked like she hoped it would, this evening she would be sipping a nice glass of wine while watching Kate, naked, laying under some horny gentleman working hard to make her scream in pleasure.

When Kate opened the door, she had the hair, nails, and outfit exactly like she and Tonya had discussed during the week.

"You look like a million bucks!" Tonya squealed as she pushed past Kate into the house. "If we weren't on a mission, I'd do you right now!! But I DO need you to take your clothes off..."

Tonya had never been to Kate's house before, but she had a sense where the bedroom was and headed that way.

"Are we having sex now? I though we were going out today," Kate replied, very willing but more than a little surprised.

"Not ALL your clothes - leave on your bra and panties. I need a sexy picture for 'The Plan'."

Tonya had developed and massaged and modified 'The Plan' - her mission to get Kate laid by a stranger - all week. Eric had heard multiple versions, and every time they discussed it they ended up having sex. After the weekend they had with Kate just a few days ago, and then all 'The Plan' sex during the week, he was a seriously satisfied man.

Kate followed Tonya into the bedroom, and in a few seconds she yelled for Eric. When he entered, they were both standing their in their underwear.

"So is part of 'The Plan' - us having sex before we go to the festival?" He asked. Maybe his conundrum would be resolved sooner than he imagined.

"No - just need a picture," Tonya said with a definite sense of urgency. "I was going to take a selfie, but it will be better if you take it. Do you have your phone?"

Eric opened the camera app as Tonya posed them. Kate was in front, matching bra and panties proudly showing off her excellent curves and ample cleavage. Tonya was behind her but just as undressed. She reached around Kate and cupped her boobs.

"Take this one," Tonya directed.

Eric happily snapped three pictures hoping one was what his wife needed. Tonya took the phone and scrolled through noticing the differences in each. She loved the way Kate looked, and she liked the way her body was just slightly visible to one side of, but behind, Kate. You could see just a hint of her own curves seductively hiding behind Kate, her own under garments there but just barely visible. She also loved the way her hands were cupping Kate's boobs.

"Hmmmm..." she said in deep thought. "Not sure my hands covering her bra are right. Try another with my hands on her hips. She reposed them as Eric lusted after the three gorgeous pictures. His dick started stirring as he remembered back less than one week ago when he fucked them both.

"OK, take this one," Tonya again ordered. Everything was the same except her hands were on Kate's hips and you had a better view of her impressive tits.

"Gladly," Eric answered as he took the requested picture. He knew his wife would eventually get the picture she wanted. He also knew he was getting some excellent jack off material for future use. He looked at it before handing the phone to Tonya.

"This is good," he said, "...and I think I know what you're after. I really like the tease of your underwear behind Kate, but what if it was just your panties? We wouldn't really see your boobs, but we would know where your bra is supposed to be, and the guy you show these to will realize you aren't wearing one. Two almost-naked women will be incredibly enticing."

Tonya thought for a second, and as she reached behind her to unsnap it Eric was snapping pictures. She posed and gave the order, and he took the requested picture. Again he looked before passing the phone to her, and again he was happy with how sexy they both looked. Still, there were never too many images for late-night masturbation, so if he could keep her going, the better those nights would be.

"Maybe the panties, too? You're behind Kate, so it's the tease of you being naked and not the full image. Just the curves of your naked body outlining the curves of her almost-naked body. Incredibly sexy!"

Tonya thought for a second before sliding off her panties. Again, Eric got in a few shots before she was ready, making sure at least a few were of her totally nude. Again she posed them and gave the order.

"Oh yeah - so fucking sexy!" Eric said handing the phone to Tonya. Tonya finally showed the pics to Kate and asked here which one she would be OK with Tonya showing to a potential conquest.

"Wow, these are sexy!" She said scrolling through them. "I think the one where we're both in bra and panties to start. We can always get more daring later if needed."

"ORRRR," Eric drawled wondering how many more times he could pull this off. "How about if Kate takes her bra off, too, and you use your hands to strategically cover certain parts so that the guy knows you're mostly naked but doesn't see the good parts? But he does see your hands holding her boobs - no way any straight guy can turn that down!"

Kate turned to look at Tonya unsure what she would say. There were no secrets between them after last week, but she was getting really horny and was almost ready to blow off the festival and move on to Threesome 2.0. Still, if Tonya could pull the plan off, a new notch in her headboard was very appealing.

"What do you think, Kate?"

Kate reached behind her back and quickly removed her bra. Again, Eric didn't wait to snap pics and got a few candid shots before the posed pic Tonya requested.

"OK, very fucking hot," he said as he drooled over the most recent pictures. Before they were posed he could see all of Tonya's naked body and Kate in just her panties. 'These will be fantastic JO material,' he thought to himself.

"Yeah, these are what I'm looking for," Tonya said before handing the phone back to him. Send me these three," she added showing him the requested pictures.

Eric sent her the pictures and sat back to enjoy the extra time he could watch them run around in the undergarments as his wife's OCD kicked in. She would not allow either of them to get dressed again until she ironed their clothes. That was at least another 10 minutes of seductive curve watching for him.

* * * * * * * * * * * * * * * * * * * *

As they drove the 10 minutes from Kate's house to the GrapeFest site, Kate was ready to talk.

"I know I've told you this already, but I had an amazing time last weekend. I really appreciate you guys including me," Kate excitedly said.

Eric wanted to say he had a great time as well, but he was smart enough to know this was a conversation best left to his female companions.

"We had a great time, as well," Tonya answered. "We've talked about that, and about our plans for today, all week. I hope you don't have any regrets."

"No, I don't," Kate answered. "Probably my only regret is we didn't do it sooner. I feel so different about myself, and things I want to do now. I feel desirable for the first time in forever, and I feel ready to be in sexual situations again."

"You should feel desirable," Tonya responded. "Taking those pictures it was all I could do to let you get dressed for our adventure today. I was thinking about you in the shower this morning and had a memorable experience. I was ready to turn fantasy to reality when we got to your house."

Kate looked extremely happy to have been part of Tonya's morning fantasy.

"How about you," Tonya continued. "Any new adventures this week you'd like to share? The next best thing having sex is talking about it. No Wait - the next best thing is watching, which I plan to do tonight, and then the next best thing after that is talking about it. So, anything new you can talk about?"

Kate told Tonya that she, too, had had a morning shower fantasy, and included all the details. She then added that she had many fantasies throughout the week, and the closer it got to the weekend the more fantasies she had. She finished with the one in the laundry room with her panties.

"Speaking of panties," Tonya said with a naughty grin, "Don't plan on going home with those. They are going home with us!"

Kate wore a massive smile as she shook her head 'yes' to agree with Tonya's demand.

"I was hoping you guys were available for dinner next weekend," she said to Tonya. She had noticed Eric always deferred to his wife during these kinds of discussions.

"Just dinner?" Tonya asked, feigning innocence.

"Well, what ever you guys are up for," Kate responded. She went for the naughty look to counteract Tonya's faux innocence.

"Hmmmm - we're probably free, but I'll need to ask my hu..."

Eric was eagerly shaking his head 'yes' before she finished her sentence.

"Uhhhh, looks like we are free!"

Eric's companions completed the dinner arrangements while he looked for parking.

* * * * * * * * * * * * * * * * * * * *

"OK, so we're looking for single guys about our age that look reasonably intelligent and are also nice to look at. When we have a couple of possibilities we'll hang out near them and observe - how do they treat other people, are they really single or just getting away from their wives for a little while?"

"And after that?" Kate asked.

"Next we move in a little closer. We laugh, put a hand on the small of each other's backs, or maybe even our butts - you know, not like were a couple but like we're comfortable with each other."

"OK, I guess I understand," Kate replied.

"Then we try to make a little eye contact, smile, see if they smile back. If we get smiles, the next time we bump into them we ask a question - something about the wine they are trying, or maybe a good local restaurant. Follow my lead."

"OK, so what are the pictures for?" Kate asked.

"Those are for when we're pretty sure we have a prospect. We're not going to get busy in the middle of the festival - we'll meet somewhere. The pictures will be to make sure they don't chicken out. We say 'if you want to see the real version of this' and agree where to meet."

"OK, that makes sense," Kate "But what if after the picture they think they will get both of us?"

"Then I tell them I am a voyeur and you have agreed to help me fulfill a fantasy - to watch you have sex. And I will add that after you are done with them they won't have anything left for anyone else."

* * * * * * * * * * * * * * * * * * * *

"Oh my gosh, where did all these men come from?" Kate asked as they walked up the main street hosting GrapeFest. She was like the proverbial kid in the candy store. Some were alone, some were with a friend, but most were with a partner. The age group was perfect for 'The Plan', and there were plenty of available candidates.

"At all these festivals," Eric responded. "Looking to either meet a girlfriend, or at least to get laid."

"Kind of makes you 'hungry' down there, doesn't it?" Tonya added with a barely-noticeable motion between her legs.

"Yeah, it definitely does," Kate answered excitedly, her head on a swivel.

They walked up one side of the street stopping at booths that had samples of wine and men. Kate would indiscreetly point out candidates and discuss them with Tonya. Tonya approved of some, dismissed others, and if they were true potentials she would send Kate a text with 'names' that would help them identify them as they continued their mission.

The first candidate was 'Mr. Tan', followed by 'Super Starch', then 'Pretty Shirt', and 'Miami Vice'. There were a few more, but these gave them a great batch to start with. At this point Eric was just a passenger in Tonya's plan. He did anything she asked him to do, enjoyed as many samples as he could, and enjoyed the MILF scenery while his cougar companions hunted men.

Over the next few hours they eliminated 'Mr. Tan' as too arrogant, and 'Pretty Shirt' after Tonya got close enough to see the indention on his ring finger where his wedding band used to be. He was either looking to cheat, or so-recently single that there was the risk of emotional baggage. They were looking for someone very-single and ready for a no-strings-attached fuck.

After lunch they started stalking 'Super Starch' (Tonya's favorite because of his perfectly-ironed clothes) and 'Miami Vice' (that perfect 'I shaved three days ago' stubble). They managed to briefly talk to each of them, and also managed to lightly touch each other per 'The Plan'. Both seemed receptive to female friendship and stayed close by as Eric, Tonya, and Kate moved down some of the less travelled booths.

"How do you think it's going?" Kate asked, obviously excited from flirting with Tonya and their potential prey.

"I think it's going GREAT," Tonya answered, equally excited. "I've noticed both of them looking when I would put my hand on your butt. I think they are both at least intrigued. If either of them approach us to talk (instead of us having to approach them), then I'm going to take the next step."

"And what's the next step?" Kate asked.

"I will send the two of you back to get me a bottle of Merlot from that booth we liked. While you're gone I will tell them I want to watch you get laid, and if they're receptive, I'll show them the underwear picture."

"OK, but what if they don't want to?" Kate asked worriedly.

"They're starting to hang around with us and make it to the same booths as us," Eric responded. "And they're guys. At this point they're probably both thinking they will ask for phone numbers. When Tonya tells them what they can have instead of phone numbers, they will be in. Guys don't turn down sex."

* * * * * * * * * * * * * * * * * * * *

"I know the people that run that winery," 'Miami Vice' said as they tried a new Chardonnay. "They're really great people and make excellent wines."

"Really?" Kate asked as she seductively smiled. "Do they have a Merlot? I think that's my favorite."