Chapter 54: 2:01 AM

It was at that point Tom realized where my cock was. But he didn’t know Jackie had been a virgin when we had taken off in the plane. He also did a poor job of reading the situation as Jackie had her hands covering her face, crying. “Holy fuck ... You two fucked on the way down? That is so fucking kinky. It had to be a blast.”

Tyleen was just as bad, “Damn ... What a memorable way to lose your virginity.”

Jackie was still crying, impaled on my pole as I quickly undid the clasp holding us together. To get the focus from Jackie, I said, “I am not sure I’ve seen the maneuver you did while freefalling in any manual. In fact, I would bet all manuals would frown on that activity.”

I had all the clasps holding Jackie’s harness to mine undone. I put my hands under her arms and raised her up a little over a half foot. There was a licentious slurp as my cock was pulled from Jackie’s sopping wet and tight passage. She wailed into her hands as I did so. It was then I realized I could’ve raised her off me while we were floating down. But then, I was also enjoying the crush of her cunt walls on my dick.

Her pussy tube was free of all impediments. The previously plugged-up orgasmic fluids were free to pass out of her hole. The first glob of our combined fluids splatted on the ground between her feet. There were two more that made lewd splashes to mix with the growing pool of lightly tinted pink excretions. The sound and feel of the cum leaving her used pussy had Jackie run away from us, bawling.

Tim, still not exactly Mr. Sensative, said to me, “You mean she was a virgin? Shit, you’re a lucky fucker. That had to be a great fuck ... That tight body of hers.” Thank goodness Leanne was better at reading the situation, and moved Tim away from me. Which was good since I was ready to deck him.

Martha did the same with her sister. “Don’t be a bitch. Go see if there is anything you can do for the girl. She just had a large cock up her for the first time. And, you heard the screams.”

Tyleen patterred off, to see what she could do in the way of help. Martha stayed with me as I removed the last of the rig and started to gather up the lines and canopy. She asked, “You mind if I ask? Why now?”

Balling up the last of the canopy, I answered, “Believe me, it is not how I saw it going the first time with her.”

“So you saw a first time?” Martha raised an eyebrow. “What were you expecting the first time?”

“I can damn sure say, it was not while skydiving,” I answered. I walked the canopy and rig over to the helper at the landing site. “Let’s just say, I figured it would at least involve a bed with a mattress.”

“So you don’t have a water bed at home, I take it,” Martha grinned. “You were thinking you would take her virginity at home in your bed. Where you would take your time enjoying all the charms she has to offer. I can say from the few I have sampled her. It would have been one hell of a night or day. Or possibly a night that extends into a day.”

Not giving her the full story, I said, “Yeah, something to that effect. Though, I wasn’t planning on pushing the subject.”

“So, again how did it happen?” Martha asked leaning in.

“By accident,” I replied. “Jackie was being her usual self. Playing with fire without the thought of getting burned. Like when she tells me she isn’t going to do something I ask. She knows she is going to do it. But she wants to see how far she can push it. Well on the way down, she pushed it too far. She was teasing me or hell maybe she was teasing herself. Either way, she had my dick head where it didn’t belong when the altimeter opened the chute. I stopped. She didn’t. That is until I was fully inside her. And damn did that hurt like hell. One second my cock head was at her entrance. Less than half a second later, I had my dick punch her cervix out of the way on the way by. My head continued up her until she got caught by bottoming out on my pecker. The whole time it felt like her pussy was ripping off my skin as she stretched.”

“You mean she took all of you in less than a second? Fuck that girl deserves a medal and hazard pay. I’ve been fucked a lot. And I mean a lot. And I wouldn’t want you doing that to me even today,” Martha stated. “That’s not stretching a pussy that is pummeling it. I’m proud that she can even stand up. When you get to the hotel send her to the hot tub. She needs it.”

“If you think it will help I will,” I said. “Anything else?”

“Yes ... Buy her flowers and chocolates and anything else she wants. I have to ask. How in the hell did you get the leverage to pump in and out of her? And do it with a cock as red as yours is?” She nodded down at my groin. “You should come up as well. After slathering your dick with a tube of triple antibiotic ointment.”

It was a strange conversation to have with her. Yet, it was like I was talking to one of my best buddies in the locker room. Nothing seemed to be off limits. And no question asked didn’t get answered in some manner. “I didn’t. I just stayed embedded to the hilt. But she did kick and move some.”

Martha pointed to the puddle of juices that had started to soak into the ground. “So how in the world is there that much spunk and pussy juice over there?”

“Simply being in her and feeling the contractions of her pussy on my dick was enough to set it off,. I replied, only slightly embarrassed, I had cum just from being in her.

“Damn boy, you got it bad for her,” Martha said. “Spewing just from being in her pussy. That is so newbie, high school stuff.”

I lied mainly to myself, “I don’t have it bad for her. I mean, I find her attractive and fun. But have it bad for her? I don’t think so. As for cumming, I think it was because my dick had been on fire and her warm juice soothed it. And her walls squeezed me over and over. Plus she climaxed as well.”

“Hell, I’ve known she has it bad for you. That is nothing new,” Martha explained. “It is like saying, Tyleen wants your dick in her as often as you will do it. Nothing surprising there.”

“I guess,” I said going to find Jackie and Tyleen. They were sitting on the hood of the car talking and back in clothes. Not their original clothes but a T-shirt and sweats. The T-shirt had on the front, “I have to take this off. Before I” On the back it had the silhouette of the skydiver on their sign and “Naked Skydive AGAIN.” The sweats were similar with the front left leg having the silhouette and “Naked Skydiving.” Jackie got off the car to walk away as I approached. The “NO Pants Allowed” went up and down covering her cute tight ass. I thought it was funny they had the T-shirts printed up in English as well.

The helper gave Martha and me the same outfits to put on. We both stepped into the clothes. It seemed completely natural to dress in front of the others. I said, “It’s time to get back. I may see you on the roof.”

Martha said, in response, “Do not forget to send Jackie up as well.”

“I won’t,” I said. To Jackie, I said loudly, “Come on. Time to get back to the hotel.”

Staying at a distance, Jackie said, “I’m going to go back with the Simpsons.”

Martha jumped into our conversation. “No, Jackie. Tyleen and I may go out yet.” They were not going to go out. Both Jackie and I knew they were not going out. It was an excuse to have Jackie ride back with me. Supposedly, we would talk about the jump on the ride back.

“Fine,” Jackie said coming back my way. She walked slowly glaring at me with each step. If there ever was someone who did not want to be near me, it was her. I held the passenger door open for her and helped her in. She accepted the help, still keeping mum. She groaned and grimaced sitting in the front seat.

She raised up her feet onto the seat keeping them a foot and a half apart with her knees even further apart. The crotch of her sweatpants was easily seen. It had a large wet spot in the center where they covered her pussy hole. The spot continued to get larger as we drove to the hotel. Every time I asked her some version of “Are you ok?” she gave some version of “I’m fine.”

We got back to the hotel exchanging no real thoughts or feelings. The crotch of her sweatpants continued to dampen all the while. The dark spot between her legs was there for all to see as she walked through the lobby and onto the elevator. Jackie did nothing to hide it from anyone looking at her.

In the room, she was just as talkative. I again tried to find out what she was thinking and feeling. Again, she didn’t give me any hints as to what she was thinking. Even when I asked her if she wanted ice cream or maybe a coffee and Baileys before going to bed or up to the hot tub. She shook her head no and said nothing.

She stripped out of the clothes from the skydiving company. I could see some pink on the inside of them when she lay them on the bed. Though she had used her dildo for years, it had not stretched her like my dick. And the extra girth had torn at what the dildo and multiple women’s and men’s fingers had left of her hymen. The evidence of it was the pink soaked into the sweatpants’ fabric.

The visible confirmation of her deflowering made me somewhat sad to know the way it had happened. She deserved better than a hard jam of my dick through her cunt. I vowed at that moment when she did ask for us to engage in intercourse, I would make it special and long-lasting. But most of all, I would make sure she enjoyed it.

Jackie left the room in a towel and nothing else headed to the Jacuzzi. Even under the towel, her butt cheeks went up and down sexily. I did notice her gait was off. She had a bit of a penguin walk. I wondered how many times that had happened in the past, if ever. I hoped the soaking she was going up for would return her to her perfectly sexy walk.

I, too, stripped and put on only a towel. I was maybe five minutes behind her. I saw Jackie’s brown hair lying on the edge of the hot tub, already with her head back. I could hear her voice but didn’t understand what she was saying. Then I noticed two salt and pepper heads barely breaking the surface of the roiling water. She was talking with the Simpsons about something. I was fairly sure, it had to do with my cock being stuck up her.

I turned around and headed back to the room. I was sure the Simpsons spoke Jackie’s language. It was something, I didn’t believe I would ever do. So I left them to talk without me. At some point in time, I was confident Jackie would fill me in.

I went to the shower instead of the hot tub. I let the women talk while I let the hot water from the shower head beat down on my dick. The spray was not too hard on my flaccid member. The water beating down on me was restorative. While it had not gotten me to one hundred percent, I was easily ninety. By morning with a little ointment, my cock would be at full capacity. My balls might be as well.

Forty-five minutes of hot water sprayed on my dick and I got out of the shower. My cock felt much better. Most all the sting was gone. After getting out I went to my luggage and pulled out my not secret stash of lube. It was water-based lube, which even had a cherry flavor to it. It was wishful thinking that I could get a blowjob out of one of the women in the hot tub. Since it wasn’t likely I would see either of the Simpson sisters, leaving Jackie as the only candidate for the job. But she likely would not be up for sucking on my dick. And I wouldn’t be asking.

The lube did more to fix the slight rug-burn type of sting going through Jackie’s vagina stretching it in less than a second caused. I sat in Jackie’s favorite chair nude watching some movie, I wasn’t paying attention to. I did though let my dick hang out in the cool air. When the credits for the movie ran, my dick was much improved and Jackie was not back. I couldn’t help but wonder if the three women were talking, or if the oral soothing took a more physical approach. Knowing what I did about Tyleen, I was betting on the more physical approach. Her spit acting as the local anesthetic to Jackie’s orifice.

Either way, I was ready for bed and in it, naked, long before Jackie came in. I heard her come in and I asked, “Did you have fun in the hot tub talking to the Simpsons?” I threw in the ‘talking to’ so she didn’t feel the need to deny any activities implied had it not been included.

Quietly from the bathroom, she answered, “Yes.” Nothing more was said as the water in the sink started, and I could hear her brush her teeth. She was backlit as she came through the bathroom doorway. She didn’t have the towel or her robe on. I did love that view. Her hourglass shape with a small heart-like shape the bottom of her pussy and the gap of her inner thighs made, illuminated. The light coming in through the window lit her once the bathroom light was turned off.

That view was great as well. Her perky breasts firmly kept their small coned shape. Her taut stomach seemed even flatter since I had seen her naked for the first time back in Washington D.C. And in the low light the faded hickeys going down her stomach were not so clear. But the purple of her cunt lips seem to have renewed their color. It was likely from the single hard blow when I was buried in her.

Her walk was much improved from earlier. The penguin-like walk was gone and her hips again had their sexy swing. It was just muted. She stood in front of the window looking out for a second before she pulled the blinds fully closed. Drawn, the blinds plunged us into complete darkness, with the exception of the red glow from the digital alarm clock. It glowed eleven-eleven.

Even after I had said, “Good night,” she slipped between the sheets, naked, without acknowledging my comment. She stayed on her side hugging the edge with her back to me. She had done something like this the first week but by the end of the week every morning she was draped over me or me over her. Thus I took it in stride, closed my eyes, and drifted off.

There is something about 2:01 in the morning that gets Jackie going. I woke up at that time, from the strange feeling someone was watching me. A sort of premonition while I slept woke me. After looking at the clock, I rolled my head in the other direction, feeling the staring was coming from Jackie’s side of the bed. That is when saw the whites of her eyes that were somewhat pink from the red glow. She had her head propped up on her hand looking at me. She didn’t change positions or say anything when I turned fully to her.

I mirrored her position raising my head up to rest it on my raised hand. We looked at each other for over a minute not saying anything. I finally ask, “What’s up?”

Though asked quitely my voice seemed to fill the room. It startled her, but she answered, “Nothing. Just watching you sleep and thinking.”

The thinking sent a shiver down my spine. I wasn’t sure if the earlier conversations with the Simpsons were to calm down a murderous rage. Or just to talk over how much she liked having a cock in her the first time. The possibilities were endless. But sleeping beside someone is truly the ultimate form of trust. So I wanted to make sure the trust was justified. “What were you thinking? Hopefully, not a thousand different ways to kill me in my sleep.”

“Why would I do that?” She asked in response.

“I don’t know. I just wanted to be sure,” I replied.

“No, not that. Other stuff,” She said sort of dreamily.

“May I ask what that other stuff is?” I asked her with the correct ‘may’ not ‘can.”

“Sure,” She said just as dream-like not getting the hint she was supposed to tell me then.

“So what are you thinking at this hour, looking at me?” I asked.

“I’m trying to remember the feeling of the orgasm I had with you in me. I remember it was powerful and mind-blowing. But the actual sensations. I can’t remember. Kind of like the pain. I remember it was painful but not the specific feeling of pain,” She said.

“Ok,” was about all I was going to add to her thoughts. I knew the body couldn’t recall the actual sensations pain or pleasure, only remembering it occurred.

She continued looking at and through me. “I thought, I would always remember the feeling and pain of having my virginity taken ... Taken doesn’t sound right. Given is a better word. I had always planned on willingly giving it to someone. But in this case, taken is actually correct.” I didn’t like where she was going but figured she needed to get the thoughts off her luscious chest.

“But now,” She continued, “Not six hours later I don’t remember the specific feeling of you being in me. Oh, I remember the pain. In fact, my pussy is still burning and sore. But I can’t recall the actual feeling of that or your sperm entering me and filling my insides. I remember it felt more miraculous than anything I have ever experienced. But nothing more ... So I don’t know. I am just looking at you hoping the feelings return.”

“Ok,” I repeated in acknowledgment of having heard her.

Then she added, “I don’t blame you. You do know that? I don’t blame you for taking my virginity. I would have given it to you at some point. Likely once we were in Texas. I guess my playing around and the altimeter just changed the timetable and manner.”

I was surprised by her admission she thought at some point she would have made love with me. As I had told her in the past that was the only way I would enter her. Who could have predicted a mishap while skydiving? “I’m glad you don’t blame me. I am sorry it happened the way it did.”

“I know. I can see it in your face. You are a sweet and kind man. You would have never done something like that on purpose. I do wonder, though, if Tyleen had the skydiving instructor set up the circumstances for it to happen. I mean, she knows me well enough to know I would play with you on the way down,” Jackie said, what I had thought on the drive back to the hotel. She leaned over and gave me a light kiss on the lips.

“So do I,” I said after the sensual heartfelt kiss.

Again looking at me, the next surprise of the not-quite morning came. “You know you can hold me. I like it when you do that.” She scooted closer but did not turn over so we could spoon together. I wrapped my arm over her and pulled her the rest of the way to me. Her small tits had their hard nipples pressed into my chest before the firm mass behind them was squashed into me. Her leg wrapped over mine opening up her vagina’s lips slightly. She used her leg to pull her pelvis tight to mine. In doing so my dick grew, going up through her partially open slit and hitting her clit as it continued to grow.

She kissed me a second time for a slightly longer time. It was more intense in those short moments than any she had given me before. She backed up only her head leaving her body molded with mine. She looked me in the eyes for a good while. She appeared to be in the final stages of a decision. A minute later, she let her decision be known. “I’m not a virgin anymore. I hope that doesn’t change things with your not entering me the first time unless we were making love. Because I want you to make love to me. Please ... I know in the past you said I had to be in my right mind to ask it. Not just filled with lust. Well, I do lust for you to be in me again. But I would like you to make love to me as only a man I love could.”

Being told to my face not something she was saying to herself that she loved me was new, but not a surprise. I loved her, as well. So making love with her would not be a lie. Correcting her, that I would make love with her not to her, was not in the cards at that moment. Later I would explain the difference. Before I kissed her, I said, “It would be my honor.”

I kissed her again and put my hand on the back of her head wrapping her hair in my fingers. Our lips were pressed together in a kiss filled with passion and lust just under the surface. Our tongues explored each other’s mouths like they hadn’t done it ever before. I took in the taste of her and the toothpaste she had used earlier that evening. She explored the recesses of my mouth. At other times our tongues danced a slow seductive dance.

Breaths were shared as she let out a low moan of satisfaction when her hand grabbed my ass. I too was enjoying her hands clawing at my butt while breathing in our shared air. Our lips locked tightly together made for one airway shared by both of us. At that moment, we were joined just not in the way Jackie was planning on. But the shared breaths and movements of lips and tongues excited both of us more than I believe either were expecting.

Jackie was panting expectedly within five minutes. I, on the other hand, was planning on worshiping her body in ways I hadn’t been allowed to just days before. I slowed our kisses pulling away when she tried to press them together tightly. I kept my lust at bay for the moment and tried to do the same with her. “Jackie, we have all night. And that is how long I plan on taking.”

She sighed, “Oh, yes.” Her lips went back to mine but without the force of earlier. She panted and shook as she maintained control of herself, despite herself. I returned the light kiss and licked her upper lip as it captured it between mine. We made out like a couple of eighth graders behind a skating rink. Passions running high but nervousness at what the next move of our lips or hands should be. The huge difference being we were completely nude while in each other’s arms.

It was that nudity, my hand explored. I had seen her body hundreds of times. And on a couple of occasions stroked much of it. This time, I had full access without concern of being turned away or overstepping. It meant my hand could slowly traverse her silky flawless back and around the sides. I glided my hand over each of her vertebrae. My fingers went around the edges in an attempt to memorize her whole body. Slowly our mouths left each other, so I could find her jawline. And Jackie could leave her lips parted and head thrown back exposing her neck to me.