Jenny's List: Day 13, 14 and so on

Day 13

I woke up in the morning with a hand on my cock. Not lips like in the past several days. It was a hand. Not that I was complaining. Jenny had hold of my cock and I loved that.

She lazily stroked it until she noticed I was awake. Then she whispered, "Fuck I hurt bad down there."

"I'm not surprised," I told her. "I think you were fucked for about 6 straight hours. To be honest, while your hand feels great, I'm a bit raw myself. I can't imagine what you're suffering through."

"I'll just warn you," she said, "I'm not sure we'll be fucking today at all. My pussy and my ass hurt way too much. Who else fucked my ass? I know Paloma did, but her dick was no bigger than a finger."

"I'm not sure. Honestly, I thought we all fucked your pussy but I could be wrong." I told her, and then followed up with, "Let's get up and get some coffee."

"Not yet, I want to finish you off first. I don't want to be bending over for the soap later and find you in my butthole." She said with a smile.

I laughed and lay back. That's when she moved her mouth down to my cock. Jenny really knew my cock at this point and knew what I liked. She licked and sucked on it until it was covered in her saliva. Then she would go down as far as she could. As she pulled back up, she would pause with the head being all that was in her mouth. There would be a swirl of her tongue like she was making sure to get any pre-come I was leaking, and then she would go back down again.

At the same time, one hand would be wrapped around the base of my cock. Her fingers would follow her lips up and down, applying extra pressure around the shaft.

Jenny's other hand would massage my balls, my prostate, and occasionally a finger would tease my anus. Sometimes she's slip it in. Other times it would just rub around it like a rim job.

Jenny continued as long as I needed her to. However, the tenderness of my cock made me more sensitive than usual. I told her I was about to come and she changed things up on me. She pulled her head away and jerked me off on my own chest. Don't get me wrong, I still got great pleasure out of it. It just wasn't the sensation I got when I came in her mouth.

Jenny jumped up and went to the linen pantry and got a hand towel to clean me up. As she did, I realized that the come kiss I had come to expect, was missing this morning. Yesterday morning she was crying because she felt like a bitch for pulling away from me. Today, she's pulling away again. Fuck, a woman can really mess with your mind. Even when it's unintentional.

The rest of the day was mostly spent where we first met; at the neighborhood pool. We swam and sunned. We talked some. Things were colder between us to be sure.

After a long day, we watched some stupid show on Netflix and she jacked me off. I tried to reciprocate but she complained about how much she still hurt. I didn't doubt it, but it seemed like a disconnect from 24 hours ago when the night ended with her asking me, "Make love to me."

Day 14

I knew we had to get up early to head to the airport so I was a little surprised when that warm sensation on my cock returned that morning. Instead of her mouth, I woke up to Jenny riding cowgirl style.

I'm not sure how long she had been riding because I had a dream we were fucking before I woke up. So I was more roused from a dream to reality than I was awakened. And it felt good.

She said, in a voice that was already near orgasm, "Let me set the pace, I'm still very sore." So I did. Jenny swayed her hips forward and back like she was listening to a slow dance song. I love the feel of her warmth, her wet and hairy pussy, and the sight of her tits. She was beautiful. She was what I wanted in life. And I knew she was leaving.

I wanted it to last but her orgasm caused such contractions in her pussy walls that she milked the semen right out of me. She collapsed on my chest briefly before hoping up and inviting me to join her in the shower.

As I entered the shower with her she said, "I want you to piss on me again."

I answered, "No, I won't do that. You associate piss with shame and humiliation. You may want our relationship to end on that note, but I don't. I love you and I want us to find a way to continue our newfound life together. I won't let you demean what I think we have."

"Fuck you," was the surprise response she blurted out. Then she soaped herself and washed her hair, all while I stood against the far wall of the shower. We were 3 feet apart but we might as well have been the 500 miles we would be by the end of her flight.

We showered and dressed. I took her to her place so she could pack and then we drove 15 miles to the airport in silence. I was hurting bad but she rebuffed every attempt I made to talk about it.

She asked me to take her to Departing Flights. Not to pack and come in. I got her luggage out of the trunk and she stood on tip-toes to kiss my cheek. She said, "Thank you for everything. Really, it meant so much too me. Please don't try to call me. I'll get in contact when I'm ready." And she walked away. Just like that.

I think I went through several stages of grief on the drive home. Denial. Anger. Sadness. I pulled over at a gas station but not because I needed gas. I needed to get off the road and cry.

The Days that Followed

For the next several days I check my phone six or seven times an hour. I didn't want to miss her if she reached out. She didn't. My mind went deeper and deeper into depression.

My friends that I had grown to know more personally, and sexually, reached out to offer their care. Ken and Amber took turns dropping in for wellness checks. Penny delivered pizzas I hadn't ordered. Jackson and Valeria both called.

After about a month, my former business had a board meeting. As a 10% owner I was expected to be there. They even chartered a private jet to take me to Kansas City.

It was great to see my old partners and to see the son of the two who had gotten married. It was fun to catch up on old times, yet I still couldn't shake the sadness.

On the flight back, there was a cabin attendant who wasn't there on the way to KC. I was alone on the first flight. She was stunning. Her name plate said she was Josie. A bleach blonde who carried herself with grace. She had muscle tone in her arms so it was clear she worked out.

Josie was very attentive to the point of outright flirting. She even said, "The captain says we're going to be flying a mile high. You have to be careful when you say that on a plain, right?"

I just smiled at her. I suspected that my partners saw my sadness and sent her as a sex surrogate pick me up. I wasn't biting. I just didn't have the psychological energy to enter into another relationship.

When I arrived home I stopped at the guard house and nodded to Ken as he let me in the gate. As I drove away, windows down, I swear I heard him say, as if on the phone, "He's headed home now."

Assuming I heard wrong, I parked my car and headed in to the house. I was greeted at the door by Penny. Sweet Penny. As bubbly and vivacious as she was, she was equally sympathetic and concerned. She pulled me into a full body hug that portrayed that concern.

As I walked in, I saw Josh, Paloma, and Amber on the couch together. Standing nearby was Jackson and Valeria. Penny said, "Mr. Johnson, this is an intervention."

I smiled weakly, "Thank you for caring. You are all special to me."

"You seem to have forgotten how special we are to you, Mr. Johnson." Paloma said as she stood. She spoke in that cute, broken English accent that betrayed her Guatemalan upbringing. (I'm just repeating in better English.) "Each of us has tried to make contact with you. To take you out or to drop by. We know others have as well."

"What she's saying is, we love you, Evan." Surprisingly coming from Jackson. "We know the pain you have in your heart, but you don't have to suffer it alone."

I was feeling both love and guilt in that moment. "None of us are Jenny, but all of us have enjoyed being with you," Amber said, again, surprising me with her mature approach for such a young lady. "Yes, we've shown our love with our bodies more than our words. But we have offered ourselves to you out of our deep respect and love for you."

Josh then spoke (it was as if they had rehearsed it. Which I'm quite sure they did. It was an intervention after all.) "What we're saying is we are here for you. Not just in the shallow way people say that. We are here for you right now. Our hearts are yours. And our bodies are yours."

I broke down sobbing at that moment. I just sat on a chair and cried like a baby.

They all gathered around me. They gathered as close as only those you had been intimate with could. It was Amber who placed her hands on either side of my face and said, "We'd like to show you how much we care. And maybe, in doing so, you'll realize how much your friends have missed you."

With that she kissed me. First she lightly touched her lips to mine. Then I felt her tongue lick my pursed lips. I opened my mouth to invite her in. She moved to sit on my lap, which seemed to cause the others to back away. While our kiss was wonderful, I didn't want them to leave. I pulled back for only a moment and looked up to see each of them undressing one another.

First Penny was naked and she came back to my side and began to kiss my neck. Then Paloma. She took the other side and began tonguing my ear. I was getting hard before but this accelerated that process.

The other three quickly joined together by the chair. They were all so close that I could smell each one. I could feel the warmth of their breath. Their skin rubbed against mine. Josh even took the extra step to rub his cock along my leg.

I've maintained all along that I'm not gay, but the exploits that Jenny and I went on for two weeks, sure had me bi-curious. It was only then that I realized that the small nudge on the side where Paloma was standing wasn't a finger. It was her little cock, standing at it's full height and unashamedly so.

The team took time to pull off Amber's shirt and then mine. Then Amber stood so they could remove her pants. Valeria and Paloma moved quickly to unbutton my slacks and slide them down. Valeria then nodded to Paloma and she moved to take down my briefs. She made sure to stroke me for a moment as she did.

Josh and Jackson put their hands under my arms and helped me to my feet and then guided me to the same spot on the floor where Jenny had been massaged that day a month ago. Amber brought her mouth back to mine and we tongue wrestled. As we did, I felt what could only be Penny's big tits on either side of my cock. Hands were massaging me and making me feel wonderful.

Valeria whispered in my ear, "We don't want to do anything you don't want us to. But we'd each like to take time to make love to you in our own way. Jackson will sit back as he doesn't have any interest in men, but Josh is available if you like. And I know Paloma want's to be included with the women. All we need to hear from you is what you want from us. Or, if you prefer, just let us offer you what we'd like to give. What do you prefer."

Amber pulled her mouth off mine so I could answer, "You all have taken me completely by surprise. You can't imagine how thankful I am. You can see how horny I am, though." I said and then continued, "I think I'd just like this to flow. Where ever it goes, it goes."

Amber smiled, Penny backed off, and then guided my cock into Amber's very wet and tight pussy. I cried again. This caused Amber to look town in fear she had done something wrong. "No, No, you're fine," I assured her. Then addressing them all, "You've just addressed and emptiness that I've had to over a month. It has hit me in all the feels."

Amber continued her riding of me and Penny came around and asked if I would like to lick her pussy. "Of course," I said, and she swung her legs over my shoulders and offered the gorgeous red haired mound to me.

At some point, someone started licking my balls and fingering my ass. I have no idea who. Really didn't much care. But it was all I needed to be sent over the edge. I took hold of Amber's hips and came deep within her.

She rolled off me and someone licked me clean. Penny stood up off me and I looked around. Valeria was riding her husband's cock, Josh was stroking his and Paloma was licking her lips. She looked so cute doing so, though I was hesitant to push her into anything more. I felt like she was a fragile person and I didn't want to hurt her.

Josh went into the kitchen and came out with a six pack of cold ones. I sat on the couch with him on one side of me and Paloma on the other. Why did I feel I was being set up.

I wouldn't be hard for a little while, so I just enjoyed watching Valeria riding Jackson's cock.

Penny took Amber's hand and pulled her on top of her in a 69 position. A red head and an auburn haired girl pleasing one another. It was heaven to watch.

Paloma reached over and began to stroke my cock. I looked over at her and she looked like she had gotten caught with her hand in the cookie jar. I gave her a kind smile and a nod and went back to the voyeuristic view in front of me.

Josh hopped up again and asked if I wanted another beer. "No," I responded, "But I'll take a bottle of water. I definitely don't want a drunk dick today." Paloma responded to this comment by going down on me. Just like the other day when she gave me a blowjob, it felt so good. She really knew how to please a guy. I began to use my hand to rub her back and she moved so that I could reach her ass. There had been no intent on my part. If someone gives you a blowjob, you respond affectionately, right? But Paloma wanted something in return.

Josh saw it right away when he returned from the kitchen. He went back into the kitchen and came out with our drinks and the olive oil. He handed me a bottle of water, put down his beer, and then drizzled a bit of oil on Palomas crack. Then he nodded to me.

What choice did I have? I reached over and rubbed the oil along her crack and she moved her ass again, giving me clear access to her little hole. So I inserted a finger to the first knuckle. She moaned around my, still flaccid, cock. She pushed into my hand indicating I needed to go deeper, which I did. There was almost no resistance to sliding my full index finger into her. Not that she wasn't tight. It just slid in around the tightness. I suspect my reaction would have been to pucker up. Not Paloma.

As I finger fucked her, I heard Valeria orgasm. It was beautiful to watch her deep dark skin against Jackson's light brown skin. When she came she slammed down hard on his cock and sat there and shook for a moment. Then she slowly got off him and padded off to the bathroom. Amber sat up from her 69 with Penny and asked, "Mr. Jackson, would it be OK with Ms. Valeria if I took over?"

"She would see it as a pleasant surprise when she comes back into the room." He invited her. (I laughed at the formality of the south. We were all naked and fucking and amber was "Mr." this "Ms." that.) Amber got up, twirled around to kiss Penny, and then moved to straddle Jackson's nice black cock.

Penny started to head to the kitchen and asked, "Can I open some wine?"

"Sure," I moaned around the loving blowjob I was getting, "Around the far side of the kitchen, where the pantry is, there's another door. That opens into my wine closet. Take your pick."

It took a moment and then I heard, "Holy shit, Josh. You gotta see his wine selection."

Josh got up to go look and it took them a moment to return. I heard the rattling of the wine bottles on racks and figured they were fucking in there. When they finally came out, they had a couple of bottles of my Stag's Leap Cabernet Sauvignon. If we had a sommelier present I'm sure they would say that it's an upscale wine that pairs perfectly with fucking.

Meanwhile, Valeria had returned and sat next to her husband and played with Amber's breasts as she rode him. Penny brought in several wine glasses and poured them and distributed them to anyone who wanted one. Amber, Jackson and Valeria all said "yes." I declined.

Paloma looked up at me and said, "Please don't move your hand." And then sat up to take a glass. She drank it with one hand as she continued to coax my cock to hardness. All the while, my finger was fucking her ass. I had even managed to insert a second alongside it.

Josh sat down again next to me and Penny backed into his cock, aligning it with her pussy, she sat down. Amber had just done the same, standing up and turning around to face us on the couch across from her, Valeria and Jackson. So I wasn't shocked when Paloma said, "I'd really like to do that too, if you are OK with it." I smiled and nodded yes.

Paloma hopped up fast enough to spill her wine, but didn't. I guess she wanted to move quickly before I changed my mind. My cock was hard enough and she spread plenty of oil on it. Then she backed into me and inserted me into her bottom. Like I said about my finger, she was damn tight, but my cock slid in nicely.

Amber said it first, "Oh, you should see the look of satisfaction on your face, Paloma. You've really wanted this for a while, haven't you."

"I love a man in my ass." Paloma replied, then turning he face to look at me, "But I really have wanted to fuck Mr. Johnson since we first met at the restaurant."

"First of all, thank you. I appreciate the compliment. Secondly, my cock is in your very tight, very sexy ass. Can you please call me Evan now?" I asked.

"We don't know each other that well, yet." She responded, "But I'd like to get other know you better."

I had to ask, "What about Cam."

Penny spoke up, "They are not allowed to have a relationship. Paloma is an employee. So they just fuck from time to time. Nothing serious."

I just had to laugh at that. Values have sure changed over my 50 years.

Paloma was working that cute ass on my cock and getting a lot of grunts out of me, when she looked over her shoulder again. "Mr. Johnson, would it be ok if I turn to face you?" And then she added, "please."

It occurred to me that this would add another layer of intimacy. It would be like "getting to know each other better." I didn't know if I was ready to be in a relationship with a transgender woman, but I was more than ready to face Paloma. I desired to kiss her, play with her tits, and .... Well if the mood hit me, I might even play with her sweet little cock.

"I wish you would," I said to her. As she got off me to turn around, Amber and Valeria cheered for us. Penny looked over her shoulder at Josh and said, "See, I knew they would enjoy each other. I win the bet." I was shocked that they were betting on us. I also knew that Josh was getting pegged later by Penny for betting against us.

Paloma faced me and straddled my legs. Then she put a hand between her legs and mine and lined up my cock to insert me in. As she settled down on my erection she took my face in her hands and kissed me. Our tongues invading one another's mouths in a very sweet way.

Paloma raised up and down on her knees and knew just how to be sure that I wouldn't slip out. I had one hand behind her back to hold her close and another between us massaging that beautifully perfect set of breasts.

I could feel her small hard cock between us and it turned me on to think she was hard for me. She ground deep into me and then back out again. Taking my full length in her ass without the wince of pain you might expect.

She seemed to automatically sense that I was getting near to an orgasm because she picked up the pace. She was moaning nearly as much as I was and I wondered if the idea of an anal orgasm was a real thing.

As I began to fell myself about to let loose, my hand just naturally drifted down to her cock. I could hold the whole thing in my fist with too to spare. Paloma pressed herself more to me and I began to shoot in her ass. As I did she groaned in a deep voice that betrayed her gender identity. I felt her come leak out all over my hand as her tongue dove deep in my mouth.

She rode me until I slipped out. Then she took hold of my wrist and brought my hand to her mouth and licked me clean all over. I caught her completely by surprise when I then put my tongue in her mouth and tasted her. She squealed a happy note as I shared her fluids.

When we separated I noticed that everyone else had stopped their fucking and were just watching us. Penny had the biggest grin I'd ever seen on her. Amber looked like she was going to come just from the show we put on.

I looked at the others and said, "Please, finish." Penny went back to fucking Josh and Amber did the same with Jackson. Valeria had three fingers up her pussy and was hard at work.

Paloma just leaned forward and rested her head on my chest. He b-cups rubbing against me, as our breathing began to come under control.

Amber and Penny seemed to be synchronized in their orgasms. A few minutes later Josh and Jackson flooded their pussies with their come. I didn't notice what happened with Valeria as my view was blocked by Paloma's hair and I really didn't want her to move. She felt so good against my chest. Like she belonged there.

The five others got up and got dressed. Jackson and Valeria said their goodbyes as Penny and Josh cleaned up bottles, glasses and the kitchen. They came over to tell Paloma they were ready to take her home but she was fast asleep.

I whispered, "She's fine here, if that's ok with you guys."

Penny beamed and said, "Of course, you two are so fucking cute."

I admitted, "I don't know what this means long term. But I promise I'll be gentle with her." Then I winked and said, "Except when she doesn't want me to."

Penny gave me a kiss as she rubbed the back of Paloma's head. Josh leaned in for an awkward hug. Then they turned out the lights as they left.

I scooped up Paloma in my arms and took her to my bed. I lay her down and then spooned her, holding her tight. Listening to her lightly snore, the dreams came easily. My life was on track once again.