Jenny's List: Day 10

"Note to the Reader: It will help with your understanding if you have read all "Jenny's List" stories in order."

Day 10

If you've been reading along, you know how my day started. She's only 4 days away from leaving my home in Florida for her home in Tennessee and I cannot imagine what it is going to be like to wake up alone when she's gone.

Today, Jenny had her mouth on my morning wood, as usual. What was unusual was that she had a lubed finger penetrating my anus. I'm not sure which woke me. Either one certainly would.

Jenny worked her finger in as she sucked, licked and stroked my cock. This is heaven. I'm just sure I died 10 days ago and this is heaven. Her finger went in and out. Each time seeking out that walnut sized organ that made my erection harder and would eventually make my orgasm more intense. Her mouth was working wonders and she quickly brought me to the edge.

I moaned, "I'm right there, please don't stop," but she did. She pulled her mouth away as her finger was removed from my ass. I missed both immediately and felt that peak and crash that comes when you edge.

"I want you to come on my face and then wash it off with your piss," She demanded. It was the reverse order of things from yesterday. I pissed first and then came. She also had stated yesterday, that this wasn't something we would do regularly. It irritated me that she was not living to her promise. However, I was about to blow my load on her gorgeous face, so I didn't object.

As I let the shower warm up, I took hold of Jenny's breasts; one in each hand. I pulled her close to me and we kissed. I really didn't want to do what she was asking me to do. I thought it was degrading. Maybe, I considered, this was just an issue from my upbringing that I needed to set aside.

Steam started to come from the shower stall and Jenny pulled me in by my dick. After getting the temperature just right, she dropped the washcloth on the shower floor, kneeled on it, and began to take me in her mouth. It felt so good. At this point in our short relationship she knew how to play with my balls, lick the head of my cock, suck in and out, and get me to moan.

Jenny also knew how to get quickly to my orgasm. She seemed to want it sooner rather than later, so she re-inserted a finger in my ass. She grabbed my scrotum and pulled down slightly, adding just enough pain to the pleasure. Then she urged me to jack myself off while she sucked and licked the head.

I went to work, joining her in the quest for my come. It was only a minute or two later and I was ready. "Here it comes," I told her. She pulled her mouth away. I continued to jack off as she took hold of my cock and pointed it at her face. I came hard and it was very pleasurable. (I don't know why that isn't demeaning toward a woman but piss is. So I decided to just enjoy both.)

When she pulled her finger out I was able to relax. My bladder was ready to explode with my morning accumulation and it didn't take another moment before I was washing her face like I had a hose in my hand.

Jenny closed her eyes and smiled as she leaned back and let me shower her with my urine. It's an odd visual effect when the yellow washes over her face. It gives the skin an unusual tone that lasts only a second before it's gone.

When I finished she stayed on her knees and kissed and sucked my cock. She said, "Thank you for indulging my perversions. I'd really like to know what yours are so we can indulge you as well. What's on your list?"

I really hadn't thought about it at all. I didn't have a list. If I did, it would have been covered by the last 9 days together, inclusive of this morning. So I told her, "If I think of something we haven't done and would like to, you'll be the first to know." She smiled, took one last dip down my deflating cock, and then stood to kiss me.

"So," I asked, "What is the kink of the day?"

"I'm not sure," she responded, "I was hoping you had an list we could work on. I realize that the last 9 days have been all about me. I am sorry I've been so selfish. I would really like to satisfy you today."

"You don't know how much your sex drive and perverted list have satisfied me. I've been blown away, figuratively and literally," I stated. "But you saying what you just did, sure makes me desire you even more."

Jenny demurred at that comment, took my hand, and pulled me under the raining shower head.

After drying off we headed to the kitchen so we could get our morning coffee. While we did, her phone rang and she asked if she could take the call privately. I nodded and she headed for the Lanai, pulling the door closed behind her.

When Jenny came back in she said, "OK, that was Penny. She wants us to be 'mystery shoppers' tonight. They have a new manager who will be handling the restaurant and they won't be there. They want us to go and eat and then give them a review of her performance. She's going to text us several questions she wants us to answer after the meal. Sound good? Then we will go to their house to tell them what we thought."

Though I wondered why she had to take the call privately, I asked,

"I'm game. Anything else you want to do today?"

"Work on my tan. I want to lay out by the pool all day and read a book. Do you mind?" She replied.

"Nope. What Jenny wants, Jenny gets. This is your vacation, babe." I told her.

She smiled, winked and then said, "I'm headed back to my place to change and then to the pool. Will I see you there?"

"Later," I told her, "I'm going to spend some time with my online investment club and catching up on things I've left undone. I think I have a panic email from the board of my old company. It's two or three days old, so I probably should reply," I laughed.

Jenny kissed me and said "see you later. Our reservation is at 7:30."

I didn't end up going to the pool. I had left the investments to the team for several days and most of them are not very good at it. We were down about 15% on the last week. It's not panic time, we were still up 22% on the year, but no one likes a loss.

The panic on the part of the board was that one of my original partners was talking about cashing out like I had. They were concerned because she was married to another of the original developers and they were afraid both would leave. I gave a call to Bart and Carole I they told me the guy got it all wrong. Carole was pregnant (and I congratulated her) and she and Bart were building their dream home. They needed extra cash. She wasn't cashing out, just selling some shares. No big deal. We made plans for them to come visit before the baby was born and for me to visit afterward.

I texted Jenny in the middle of that mess and told her I would pick her up at 7:15. The drive to the shop was only about ten minutes but parking in that area was tough so we might expect a five minute walk.

At 7:15 I was on time at her place and Jenny was out the door and ready to go when I pulled up. I hadn't expected that. The restaurant was actually only 5 minutes away and parking wouldn't be a problem. I was just hedging my bets thinking she would run late. Apparently I didn't know Jenny as well as I thought.

Our time at the restaurant was excellent. I hadn't realized just how nice it was. I thought it was a pizza place. I had never been there, I only ordered delivery. Instead, I found the menu was varied. The atmosphere was very relaxed, as I expected from Josh and Penny. Yet, the staff was very professional. Not stiff in the way they served, but they didn't miss a beat.

As for the manager, if Penny hadn't told us that the manager was a "she" we couldn't have guessed who it was. There was a guy, named Camden, who was behind the bar most of the evening, offering direction to the servers. He was also the bartender, but looked very much in charge.

Paloma, was the actual manager. She was very sweet and attentive, to all the patrons. She came by our table twice to see how we were doing. We witnessed how she handled a customer whose steak was not done right. She disarmed him with her charm and the meal was corrected very quickly. Overall, job well done.

When we finished our meal, Paloma greeted us one more time on our way out the door. We walked to the car and then made the short drive to Josh and Penny's house.

Penny greeted us at the door in her daisy dukes and a tight t-shirt without a bra. I had a feeling this was going to be a fun night. Josh called out from the kitchen, "What can I get you to drink?" I chose beer and Jenny chose wine.

We sat down and gave Josh and Penny our evaluation of the dinner. We offered very high marks on everything. It was a pleasant experience. I mentioned Camden at first. Penny nodded, "Cam's the bartender and a 10% partner with us. He's been there since we opened. As part owner, he oversees things carefully but really prefers to be behind the bar and not in charge. That way, when it's closing time, he gets to leave before the manager and get home to his wife and kids."

"What I really want to know about is Paloma," Penny inquired. We gave high praise and said she seemed to be in charge, respected by the staff, and competent in handling the duties.

Penny and Josh looked at each other with a knowing glance that said, to me, they felt like she had been the right choice.

Josh said, "Tell me how she was dressed."

Jenny spoke up, "She had on black slacks and a white button down shirt. It was unbuttoned to her breasts and she was wearing a black camisole. It showed cleavage but not too much. I thought it was very appropriate to what I think you were going for in your restaurant. The other servers were dressed in a more relaxed manner, but Paloma's outfit made it clear that she was in charge without having to say it on a name tag. I'd say you made a good choice."

Penny turned to me and asked, "I'd like to get your take on her. What she wore, how she carried herself, what were your impressions of her, as a woman."

I thought this was a very odd question. In any interview or employment situation this would have been completely out of bounds. But, they asked so I answered. "She's very attractive. I assume she's South American. I did notice the cleavage for sure, but again, it wasn't over the top." I said defending her.

"What about her ass," Josh asked.

There it was again and it had sexual harassment written all over it. I was concerned. "Josh, I think you are treading on very thin ice here. You could lose your whole restaurant over this line of questions. Since you asked, she had a great ass, though," My inner teenager couldn't help the last part.

Penny interjected, "So bare with us on this line of questions for a moment, please. Did you think she was an attractive woman. One, if the circumstances were right, you'd love to have sex with."

I reluctantly turned to Jenny and we both agreed, "Yes, I'd love to fuck her," we said in unison and laughed.

Penny said, "OK, Josh, you get to pay up on this one. Josh and I had a bet and he loses. Let me explain to you. Paloma is trans. She's from Guatemala. She had the good fortune of coming to the US on a student visa. When we first met Paloma she was living as a man, but in our interview for a dishwasher she said she wanted to transition. We have secretly been helping her. Our bet was that I believe she passes completely as a woman. Josh thought you'd pick up on the fact that she's trans. Let me be sure, you didn't right?"

Jenny spoke up first, "I had no idea. Now I want to fuck her even more."

I followed with, "I would have asked her out if the circumstances presented themselves. I had no idea."

Penny beamed with pride, "I have been coaching Paloma that there is a difference between living as a trans and living as a woman. Paloma is a woman through and through, so she's been working on being a woman on the outside as well. I'm proud of how far she's come from an effeminate boy to a gorgeous woman."

"Wow," I said, "You've done great with her because I really didn't notice at all. I thought I was well attuned to such things but I missed it."

Penny also offered, "Florida can be quite conservative. We want to set her up for success and we were afraid that if she came across as trans she might struggle to gain respect as a manager. We are very proud of her."

Jenny asked, "So what was the bet?"

"Well," Penny said, "We assumed you'd come over with a hard cock and a wet pussy wanting to play with us. Josh said you would notice Paloma was trans and I said you wouldn't. Whoever lost, has to sit out this sex session except to serve drinks, provide towels, or whatever we need. They have to go to bed horny and unfulfilled. Looks like I'll fall asleep with his hard-on poking my back all night." She giggled.

In my mind I was happy with this result. I know Josh wanted to engage in sex with me and I had not been down for that. So with him out of the equation, it would be Penny, Jenny and me. I was really looking forward to this evening.

Josh got up and walked out back to the bedroom. "He'll be back. He has to dress the part. Now, we should get naked. Evan, can I undress you?"

"Of course," I said with a big smile.

Penny stepped up to me and unbuttoned my shirt and pulled it off my arms. She pressed those huge breasts against me as she worked her way to her knees. Then she unbuttoned my slacks and pulled them down. When they got hung up on my leather flip flops, she took those off and then my pants.

Then she moved back to my boxer/briefs and rubbed my hardening cock through the fabric. She took hold of the waist bands and pulled my briefs down. As she did my cock popped out and slapped her in the forehead. She laughed and gave it a slap back, "If you hit me, I'll hit you back," she said in a childish voice. She was getting me harder by the moment.

My attention had been on Penny. So as she turned and said, "Let's get you next Jenny," we found that Jenny was way ahead of us and was naked and approaching.

"Evan, can you help me strip Penny?" She asked.

"Of course," I replied and began to peel off her shirt and pull it off her arms. As I busied myself with her tits, Jenny went to her knees to remove the shorts. After a moment, Penny shifted her stance and moaned. I knew that meant that Jenny had her fingers or mouth at work on Penny's redheaded pussy. Penny and I kissed as she moaned into my mouth.

As we were warming up to one another, when the doorbell rang. "Josh," Penny called out, "Get the door, dear."

Josh emerged from the bedroom in nothing but a jockstrap. His huge cock barely constrained by it. When he passed by us on the way to the door, I noted two things. First, he was walking funny. Second, he had a butt plug up his ass, which explained the walk.

I guess I should be used to being naked around Josh and Penny when they open the door to an unknown visitor, but this wasn't something more normal people did.

Josh opened the door and said, "come on in. They've already started."

A short, auburn haired young woman walked in. She said, "I see you lost the bet, Josh." Then she threw him her purse. As she walked straight over to us. The stranger tore off her shirt. Her breasts were firm and pert, b-cup, I guessed. She was toned and had the faint signs of six-pack abs.

When she got to us, she dropped to her knees and took my cock in her mouth. Not what I was expecting. As she sucked me to full hardness, Jenny looked up to me with a questioning face. I shrugged that I had no idea who she was. Penny broke the ice by introducing us. "Evan, this is Amber. The girl from security in your neighborhood. She said she really wanted to blow you. I guess she meant it."

Damn Girl, I thought to myself as she made it clear this wasn't her first blow job. She was real good. Maybe on par with Joy from last night.

As Amber did her work and Penny rubbed her breasts on my hip and Amber's head, Jenny whispered in my ear, "I decided my list included enjoying the man I love having sex with two other women and me. You got to be a part of my mmmf experience. Now you get to enjoy your own fffm experience. And remember, Josh is here in case we need him for anything." I had no idea why I might need Josh, but the rest of it sounded great to me.

The girls led me over to the rug and laid me down on it. Jenny and Penny moved their tits to my face. I suckled for a while. Penny's huge, areolas and large, hard nipples in the bright pink of a pale redhead. These contrasted with Jenny's c-cup breasts with small areolas of darker, brownish pink. I was in heaven. And Amber was still between my knees.

"Ladies, do you mind inviting Amber up here where I can finally meet her?" I asked.

Amber worked her way up my body, slowly. She kissed her way up my stomach and took time on my nipples. All the while her hand had hold of my cock. When we were face to face, "I said, good to meet you."

Amber smiled in a way that lit up her whole face. If Penny is cute, and Jenny is beautiful, Amber was gorgeous. How a 50 something guy ended up looking into the deep brown eyes of someone this unbelievably attractive, I'll never know.

Amber broke my mesmerized stare saying, "I have wanted to thank you for so long. I love my job. And I really have loved getting to know Ken. I call him my anatomically correct, Ken Doll. But I wanted to express to you how lucky I feel that you gave me a job."

I was about to object. I hadn't met her at all. I only reviewed her resume and used my computer skills to do a deep dive on her background and socials. Then I signed off on hiring her. But when I opened my mouth she inserted her tongue and I figured the point was moot.

As Amber assaulted my mouth with her tongue, I felt the other two suck on my nipples and rub themselves up against me. I was luxuriating in this bath of flesh and lips and tongues. I could feel a hardness that was a strong as ever before. When I subconsciously reached down to stroke myself, I was joined by multiple hands. What a thrill.

Amber pulled away from our kiss and asked, "Would you mind licking my pussy?"

A moan escaped my open mouth and I invited her, "Bring it to my mouth."

Amber disentangled from the other two and put her knees on either side of my face. Then she lowered herself to my mouth. Unlike Jenny and Penny, Amber was clean shaven. I think that's an age thing, though I really couldn't remember how old she was. I do know she was old enough to pass the licensing that allowed her to carry a firearm while on security patrol, so that was old enough for me.

With her lower legs blocking my arms, I couldn't use my hands to help part her lips. I used my tongue to do that task and she helped by using one finger to rub her clit. My tongue darted inside her fleshy folds. She was wet already and she even tasted young. I'm not sure what I mean by that, but it was different from the taste of Jenny, or Penny, for that matter.

I lapped at her as she rode me and fingered herself. From below I felt a mouth take my cock into it. I think it was Penny. I had become familiar with Jenny's way of sucking and this seemed different. I did a mental count of hands, boobs, arms, legs and lips and I was sure it wasn't Josh. I wouldn't put it past him to join in while my vision was obscured by Amber's sweet pussy. I relaxed trusting he was honoring the terms of the bet. I assumed he was on the couch, wishing he could join in.

It couldn't have been 20 minutes and I was on the edge of coming. Though I hadn't fucked anyone yet, we had traded places with our pussy eating and nipple nuzzling. I didn't want to finish too soon, so I moved away from the group. They looked up at me with questions on their faces. I said, "I'm about to pop and need to relax a minute. Please, pleasure each other while I watch. That will turn me on without making me pop."

I moved to the couch where Josh was sitting. His jockstrap was strained by his aroused cock. I can only imagine the feeling he had from sitting on that butt plug. To prey on the bet a little, I said, "Josh, I could use another beer." Then turning to the ladies who were two on one on top of Amber, I asked, "Ladies do you need anything."

Amber moaned, "I could use a bottle of water."

Jenny, whose face was buried in Ambers pussy uttered a muffled word and shook her head no

Penny said, "I could really use a cock, but not from you Josh. That's the rules. But if you'll bring my strap on, lube and a beer, I'll be satisfied." She then bent her head back to the smaller tits of Amber.

Josh jumped up from the faux leather couch to do our bidding. I noticed the fabric was slick from what I assumed was his sweat of anxiety of watching without touching himself.

When he returned he had a dildo in hand that was roughly the same size as his cock. It was attached to the leather straps of a strap-on. He handed me my beer. Then he handed Amber her water and Penny her beer.

Josh then took olive oil, Penny's lube of choice, and rubbed it up and down the dildo like he was jacking it off. He patted Penny's ass and she adjusted herself to make her pussy available to him. He inserted the dildo, slowly at first and then began to fuck her hard with it.

Penny moved her face to Amber's and offered her tongue. Amber sucked on it like a tiny cock. At the same time, Amber was moaning and writhing. It was only a minute later and Amber was coming. She stretched out straight legged, toes pointing, and screamed into Penny's mouth. Then she began to buck and thrash. Jenny was treating this young lady to pleasure she barely knew before.

As she finished, Jenny sat up and wiped off her face. She smiled at Amber, then looked over at Penny and Josh. "Josh," she said, "you can go back to the couch. I'll take it from here."

Jenny began putting on the strap on as Josh picked up the oil (so as not to get it knocked over) and returned to the couch next to me. I noticed he say very close; shoulder to shoulder and thigh to thigh. I knew what he wanted. I decided to allow him the press of flesh even though he wanted more.

Jenny got behind Penny and resumed the fucking. Amber watched and drank from her water bottle for a moment before setting it aside. She then moved under Penny in a 69. The lesbian show was amazing to watch.

I began to stroke myself and noticed that Josh was watching me more than he was watching the women. Knowing he wasn't allowed to come, I decided to indulge his gay fantasy of me. "Josh," I instructed, "Use the olive oil and jack my cock. Not hard and fast, I'm coming in one of those ladies. But you can help me get hard for them."

Josh almost leaped off the couch to reach the oil. Then he returned and splashed, not poured but splashed, oil on my cock and took hold and jerked me. Jenny turned and smiled with lust as she saw what I was allowing.

Soon, Penny and Amber were coming again. I guess the pressure from fucking with the strap on also pressed against Jenny's clit because she came as well.

We all sat and enjoyed more drinks for a while. Josh lazily jerked me off. That was all I would allow him. But it worked to get his cock real hard. The fabric of the jockstrap was clearly uncomfortable for him. So I reached over and freed his cock from its confines. He was so excited already and my touch caused him to moan and drip a small stream of pre-cum from his tip. Penny saw this, walked over and scooped it up with her finger and fed it to him, saying, "Shame on you. You almost came. You know that's not allowed." They smiled at each other.

After a few more drinks, Jenny lay on her back and said, "Lover, come lick my pussy, please," as she undid and removed the strap on. I would have moved quickly but I had a difficult time getting Josh to let go of my cock.

I said it before and I stand by it. I much prefer a hairy pussy to a bald one. I also love eating Jenny's pussy. It is like cuddling up to a favorite pillow. I went to work with my tongue and fingers. I moved slow at first. She was already sensitive and I wanted this to last a while.

I heard a voice in my ear ask, "Mr. Johnson, can I suck your cock some more." It was Amber and I gladly nodded my yes. I was on all fours and between Jenny's legs. So Amber got behind me, laid on her back, and shimmied between my legs and began to blow me.

Penny then whispered in my ear, "I want to be part of pleasing you too. Can I play with your ass." I knew how much pleasure prostate play can bring me, so I nodded again.

I felt the olive oil splash on my ass and a finger work it into my anus. With my tongue licking Jenny, I moaned my pleasure at what the other two girls were doing. Jenny shuddered at that.

Eventually, Penny worked in two fingers and I felt full. But she wasn't satisfied with that. "Mr. Johnson, I bet you could take three of my fingers," I heard from behind me. Then she went for it. It took a moment to adjust to those three fat fingers. Lips working my cock really helped I think.

After a few minutes Penny asked, "Can I try to fuck you with my strap on."

"Carefully," was the reply that came out of my mouth, and I couldn't believe I had said that. The dildo was far bigger than her three fingers.

I felt more oil applied and Penny slowly worked in the head. I think I screamed into Jenny's pussy, like the last time this happened with a much smaller dildo." The pain was searing. But as she slowly worked up to moving in and out, I found my ass give way to accommodate the girth. Eventually, I have to admit, it began to feel good.

This went on for a while and then Penny pulled out. I pulled my head away from Jenny's now convulsing pussy and begged, "Please put it back in. I am so close to coming."

Jenny took hold of my hands and crossed her legs, trapping my head. I didn't plan on going anywhere but, whatever. Amber, wrapped her arms around my knees and pulled them wider so my ass was wide open. Penny said, "Here it comes." And the dildo slipped back in.

God it felt good. It felt big. And it felt different than a moment before. To this day, I can't tell you for sure that it wasn't Josh in my ass. No one said anything later, though a look of guilt was on all their faces.

Jenny's convulsing turned into a full loud groaning orgasm. As her juices flooded my face, Penny's dildo sped up the anal assault. And Amber brought me to the edge and then over it. I groaned into Jenny's pussy once again and unloaded my semen into Amber's hungry mouth. All the while that dildo kept me excited as it passed over my prostate with each thrust.

The girls moved quickly after we all came and the dildo was pulled from my ass. Only then did Jenny release my head from between her legs. I collapsed on my side and looked at all of them. Each wearing a fake innocence on their faces.

I looked to Josh who was sitting on the couch with a huge hard on. It was slick with oil, but who's to say he didn't do that to himself on the couch as he watched? I just couldn't be sure. And, as I said, no one ever fessed up. Secretly, it didn't matter. It felt damn good. I didn't tell them that.

Penny demanded that Josh clean everyone up as we sat on the couch and surrounding chairs. Jenny's wet pussy was first. He licked up and down her wet thighs and then used a towel to dry her. Then he went over to kiss Amber, who apparently hadn't swallowed yet. He looked a me with a shit eating grin on his face. Or was that a come eating grin?

He nearly deep throated Penny's dildo and then wiped it clean as well.

We drank for a little while longer as we rested up. There was still one girl in the room I hadn't fucked. I really wanted to get my cock into Amber. Jenny saw me staring at her and she broke that ice, "Amber, I think Evan would like to fuck you. Is that OK?"

"Mr. Johnson, it would be my pleasure," Amber responded.

She got up from a spot on the floor where she had been sitting. Then she relocated to my lap. She straddled my legs and allowed herself to sink down on my cock. Damn, that young pussy was tight. I understood that she and Ken had been fucking. I also assumed that she was on the far edge of promiscuous, but it hadn't loosened her any. What a feeling. This could have been Jenny's ass, as tight as it was.

As Amber rode me, we kissed and I sucked on her nipples. Penny said, "Jenny, suck Josh's cock. Remember, though, he's not allowed to come." That sounded like pure evil to me, but Jenny complied and Josh didn't resist.

In the meantime, Penny was licking my balls. No doubt she was also getting her share of Amber's wetness as it seemed to flood out from between us.

I would have liked to last longer. However, I knew it was likely I'd have more chances to enjoy this sexy girl. Instead, I pulled her close and told her I was going to come. I took over the pace and fucked up into her. Maybe 10 strokes later and I announced my orgasm and followed with a flood of come.

Penny hadn't missed a beat. She kept licking until Amber sat up tall and let my cock fall out. Penny replaced Amber's pussy with her mouth and cleaned me off, as I sat spent and satisfied.

Jenny stopped what she was doing so Josh didn't come. Penny assured her, "It's OK, he'll get his early in the morning."

Amber got up first to dress. I followed and then Jenny. I took a moment to tell Amber how glad I was to meet her and looked forward to many more meetings over time. She kissed me and Iour tongues wrestled briefly. Jenny pouted and said she was jealous, so Amber kissed her too.

We laughed as we waved goodbye to Josh and Penny and headed for the door. Josh's cock was still standing up hard and I was pretty sure Penny wouldn't let it go to waste.

Back at my house, Jenny and I showered off and climbed into bed and quickly drifted off to sleep.

(Hey reader, Thanks for giving me high praise on my previous stories. I hope you'll leave a comment on this one. What else would you like to see in Jenny and Evan's relationship? How would you like them to live out their next few days together?)