Dana's Side

Wednesday

I had a test that morning, so I got up early. I ate breakfast, then went upstairs to shower. Before I did, I put on some shiny red lip gloss and took a closeup of my lips. At exactly 8 am, I texted the picture to Jack, with the message, "7 hours."

In the shower, I shaved off my pubic hair, as a little extra surprise. After my shower, I dressed for school, more comfortably than I had for Mr. Stone, but still put together. I still had a reputation to uphold. The test was not too hard, and I had used some of Jack's techniques to study, so I was pretty confident. I chatted briefly with some of the girls, and then went to get a quick manicure—bright red and shiny. I got home, ran upstairs and took a picture of my pussy, being touched by my manicured fingers, and texted it to Jack at 1:00, with the message, "2 hours." If he wasn't getting excited, that picture was likely to do it.

I started to gather my materials and props, and took all of the clocks out of my room. I wanted him to lose track of time and just enjoy the experience. I was getting excited, too. I had never done anything like this, and I was turned on by the thought that I would be totally in control of Jack's pleasure, that he trusted me to do it right. I knew that he would make sure I enjoyed myself, because I believed that he got pleasure from giving me pleasure. I wondered what my friends would think of this, and I realized that I was glad that I hadn't discussed it with them.

I put on some more of the lip gloss and took a few more pictures for later texts, pictures of my breasts, my butt, naked on the bed, etc. At 2:00 I sent him a picture of my hand cupping my left breast, with the message, "One hour". I put on my new leather bustier and corset, tying it tight to accentuate my waist, black lace split crotch panties, and black thigh high boots with spike heels. Over that, I wore a simple white cotton robe, which I closed tightly, so all he would see initially was the robe and the boots.

At 2:30, I sent another text, of me biting my right nipple and the message "30 minutes." I could picture the look on Jack's face as he got each text, and it got me hot. At 2:45, I sent another text, "15 minutes. You'd better be driving," with a picture of my ass, showing my pussy lips from behind. I waited 5 minutes before texting, "10 minutes. You'd better be in front of my house," with an attached picture of me fully nude, holding my breasts.

I walked down the stairs as I heard a car screech to a halt in my driveway, a door slam, and someone pounding at the door. I opened the door and gave him a full view of me, in the robe, with the boots. He looked at me hungrily, and I could see a huge bulge in his shorts. It appeared that my texts had their desired effect. I let him into the house and closed the door behind him, leaned up and kissed him hard on the lips. I looked at my watch. "Early," I said with a smile. "Good boy."

I silently led him upstairs to my room, handed him a matching, but larger, robe and told him to get undressed, as I walked out of the room. I came back and took his clothing, including his watch and phone and put them in the bathroom. Then I waited, to increase his anticipation, until I guessed that he was close to boiling over, then waited another 5 minutes. Then I knocked on the door.

"Who is it?" he asked.

"It's Dana. Can I come in?"

"Sure," he said, "You can come in."

I entered the room, and he was sitting on the end of the bed, in the robe, looking a little apprehensive. I opened the robe and gave him the chance to take in the outfit that I had chosen. The look on his face alone made it worth the effort. He drank me in and just stared.

"Oh my god, Dana, you look unbelievable," he finally said.

"Thank you," I responded. As I promised, today is about your pleasure, and I am glad that this pleases you."

"Oh my god, yes," he said.

As I had expected he was incredibly aroused, and I wanted to calm him down first.

"Please take off your robe and lie down on the bed, on your stomach," I asked, in a tone that didn't really allow for dissent. I saw his throbbing cock before he lay down. I put on some quiet, instrumental music and said, "I thought you might be a little tense—actually, I hope that I have made you a little tense--so I thought you might like a relaxing massage. I grabbed a tube of massage lotion and, rubbed it on my hands to warm it up and began stroking his strong, slightly hairy back. I carefully rubbed and kneaded his back, head, shoulders, legs and feet.

I then asked him to turn over. He again stared at me, with lust in his eyes, reflected in the fact that his cock was rock hard. I knew that if I touched it he would explode. Instead, I squeezed out more lotion and massaged his face, chest stomach and legs. I ignored his twitching cock, to further tease him to an incredible orgasm, when I was ready to let him let loose. I decided that I had gone on long enough, so I put more lotion on my hands and began to rub his cock, from the bottom to the tip. Every time I sensed he was about to cum, I slowed down and he would calm down. I had seen that he had good control before, but this was pretty impressive. But now it was time to let him have his release.

I unlaced the bustier and tossed it on the floor, giving him a view of my breasts, "Do you want to cum on my tits?" I asked. I think that he was so overcome by the situation that he didn't answer, so I repeated, "Do you want to cum on my tits?

Finally, he panted, "Yes, yes yes," looking a little crazed.

I grabbed his hard cock, pointed it at my chest and started rubbing until he shot an enormous load on my chest, some of which got on my face and stomach. I kept pumping his cock until he stopped cumming, smiling at him all the while. I rubbed some of the cum into my tits, and he just stared at me, smiling and looking incredibly happy. I realized that I was dripping into my panties

"Was that good for you?" I asked.

"Oh my god yes," he panted.

"Me, too," I responded. I grabbed a towel and wiped myself off and cleaned the cum off the bed. Then, I leaned down to the bed and licked off the cum that was on Jack's body and now limp cock.

Now that I got the first orgasm out of the way, it was time to up the ante a little. "You said you trust me, right?" I asked.

"Yes, I trust you."

I kissed him, hard and passionately. "O.K., then," I said, "lay down on the bed, on your back."

He did as I requested, and I reached into a bag and pulled a bunch of scarves out. "Tell me if this hurts," I said as I tied his hands and feet to the bed frame so that he was spread-eagled on the bed.

He looked a little nervous, but intrigued, as he continued to stare at my almost fully naked body. I removed the boots, slowly and sensually, and then reached in the bag and pulled out a blindfold, which I put over his eyes. I walked out of the room and changed into a see through camisole which I thought he would like, and thigh high black stockings. I let him adjust to being tied up and blindfolded. I once let a boyfriend to this to me, and I remember how, once I got used to it, it was incredible, because all of my senses were heightened. I waited for a few minutes, which I knew probably felt like forever to Jack.

I quietly reentered the room and saw Jack, laying quietly, his hairless chest moving with his breath and his cock lying limp between his legs. That was not going to last, I thought. I picked up a feather and began to lightly stroke his stomach, moving on to his chest. He was ticklish, and started to wriggle on the bed, pulling against the scarves. I kept tickling him with the feather, moving on to his small brown nipples, which hardened. His cock began to stiffen as I brushed the feather over his body. I started to use the feather on his growing cock and his balls, and he started to moan as he got harder and harder.

Time for the next step. I leaned over and gently kissed and licked his chest, so that just my lips and tongue touched him. I nibbled on his little nipples, which made him gasp before I kissed up his chest to his neck, lops and face. Reversing course, I kissed down the right side of his body, down his right leg, sucked on his toes, then up the left leg, the left side of his body, then down the center of his chest, his belly and finally gave a few kisses and licks to his now hard and twitching cock. He was writhing with pleasure, when I stopped and got off the bed.

I took off the blindfold and he blinked a little before he was able to focus on me.

He smiled and said, "Amazing."

"Thank you, I replied, as I removed the camisole, then lifted my right leg up on the bed and slowly removed the stocking before doing the same with my left leg. I was now fully nude.

"Even better," he said, dreamily.

"Thank you," I responded again.

I turned, to give him a view of my ass, then walked to the end of the bed, crawled between his legs and, without any further ceremony, began giving him a blowjob. His cock felt great in my mouth, and I wanted to do everything I knew to make him crazy with pleasure. I sucked and licked him and he started to buck his hips and pull against the restraints. I stopped my oral ministrations, and untied the scarves.

"Please get out of the bed and stand up," I directed, and he did. He was standing, legs slightly spread, with his cock, dripping wet with my saliva, sticking up and out. I put the blindfold back on him, which he meekly accepted, then got on my knees and slid under him, facing forward. I grabbed his cock and stuck it in my mouth and down my throat, so deep that his balls bounced off my head. He began to moan and whimper, and that increased as I started to slide his cock in and out of my throat while gently twisting the shaft. Jack was squatting and standing to meet my movements, and began to pant and growl. He yelled out and came, a huge load of cum shooting down my throat, which I swallowed, then sucked his cock until he was done.

I stood up and took the blindfold off, and gave him a big, tight hug, which I held for a while. It felt nice feeling his warm body against mine.

I had him sit on the bed, and I went to my dresser and pulled out a joint, which I lit and took a big hit from before passing it to Jack, who did the same. We passed it back and forth, smoking in silence, until the joint was done. I began to feel a little giddy, and weed, for me, always heightened my feelings, especially sexual feelings, so I was looking forward to the next activity.

Based on what I knew about Jack, he was enjoying my attentions, but I guessed that he would want to reciprocate. But I had told him that this was all about his pleasure, so I asked him, "Would you like to lick my pussy?"

His eyes lit up, and he said, "Actually, I really would," and that was something I really liked about him.

But, instead of laying on my back, as he would have expected, I rolled onto my stomach, and lifted my ass in the air. He didn't hesitate, and plunged right in, gently attacking my pussy from behind. It would have been good under normal circumstances, but after spending the last while catering to Jack, and getting high, it was incredible. I reached behind me and began to finger my ass, sending additional shivers up my spine. Jack did know how to take a hint, and he began to rub my asshole while still licking my pussy. I had him stop, and said,

"Please open that drawer," I asked, pointing at the night table.

He did, and saw the condoms, lube and vibrator that I had put there.

"Would you like to use them on me?" I asked.

"Of course," he responded.

It looked like he knew what to do (from Cara, maybe, I thought?) and he put some lube on his finger, and began teasing my ass with it. I felt myself relax and he was able to slide his finger in a little. I was tingling all over, when he picked up the vibrator and started teasing around my pussy while pressing his finger into my ass. This was unbelievable, and I began panting, writhing and screaming. My sphincter relaxed more as he continued fingering it and using the vibrator on my pussy. I was dripping wet and crazy with lust when he put the condom on and lubed it up, slowly pressing the huge head of his cock into my ass. I pressed back, desperately wanting him to fill me up, until he was in as far as possible. I felt full and amazing.

Then, he pressed the vibrator deep into my vagina and thrust it in and out, while doing the same with his cock in my ass. The sensation was more than I could take. I was thrashing and writhing uncontrollably, amazed that Jack was able to stay on top of me. I was screaming his name at the top of my lungs when I had what was probably the most intense orgasm of my life. It felt like it was never going to end, and I was hoping it would never end. Every nerve in my body was firing with pleasure and I started to laugh. I felt Jack cum into the condom in my ass, and he pulled out the vibrator and his cock at the same time and I collapsed on the bed, gasping for breath and laughing. Jack stroked my back gently and removed the condom, tied it off and put it on the night table.

When I was able to move again, I got up, and pulled out two cold bottles of water from a cooler that I had set up, and we sat on the bed, naked, drinking. I smiled at Jack, and he looked at me tenderly.

"Are you having fun?" I asked.

"Best time ever," he responded, and I kissed him on the lips.

I wanted more, and I knew that the next thing would be good for both of us.

"Stay there," I said, and I grabbed the vibrator and lay on the bed, with my head propped up on the pillows. I turned the vibrator on and masturbated as Jack watched, staring at me. After starting on my nipples, I moved down to my crotch and teased myself a little before sticking it in and out. It felt almost as good as when Jack was doing it while fucking me in the ass, and I started to moan and writhe, bringing myself to another excellent orgasm. As expected, Jack was hard again, and I asked him if he would like to kiss my tits. I knew he loved kissing them, so I wasn't surprised that he did. He started to kiss and suck on them, and I was purring with delight.

Then, I asked him if he wanted to fuck them, and again I wasn't surprised when he did, straddling my waist and sticking his huge cock between my large, round breasts. I was able to reach the lube, and rubbed some on his cock. He started to jam his cock between my tits, as I squeezed them tight around his shaft. When his tip came close to my mouth, I flicked out my tongue or lips to touch it. At the same time, he was rubbing my nipples, which felt great. I could tell he was reaching a climax, and he yelled out that he was cumming. I opened my mouth and received a blast of cum, some of which sprayed on my chest and face. He looked so happy, I started to laugh after I swallowed. He rolled off of me and I cleaned myself off and snuggled into his arms.

I got out of bed and said, "O.K., shower time."

We put on our robes and went to the shower. I looked at the clock and saw that it was about 7, so we had been going for about 4 hours, just about what I had figured. I turned the water on, and when it was hot, I took off my robe and went in. Jack watched me get wet, then took off his robe and joined me. When he got wet, I started to lather his body, paying special attention to his cock, which rose to attention. I handed him the soap, and he lathered me up, starting with my back and butt, teasing my asshole, which made me yelp. He pulled me toward him pressing his chest to my back, his cock pressing between my ass cheeks and reached around, vigorously soaping up my tits, belly and pussy. It was warm and it was hot, and I wiggled my butt against his cock. Jack took the hand held shower nozzle and rinsed me off, and spent extra time shooting the hot water against my pussy, and I felt tingling feelings inside me.

I turned to Jack, whose cock was hard and trembling, and said, "The one place you haven't visited yet is my favorite--that is why I saved it for last."

I grabbed him around the neck and lifted myself off the floor and wrapped my legs around Jack. He grabbed my butt to support my weight as his cock slid easily into my slick vagina. The feeling of him inside me, and holding him close, and the hot shower water was incredible. Jack took a couple of steps forward and pressed my back against the cool tile shower wall, and began to thrust into me harder. I squeezed my legs in time with his rhythm. Jack seemed to be able to go forever, probably because of the number of times he had already cum, which was part of my plan.

Steam filled the shower stall as we fucked violently against the wall. I was reaching yet another intense orgasm when I felt Jack cum, and I gasped, shook and yelled out. I was feeling amazing, and I unwrapped my legs and lowered my legs to the ground, immediately dropping to my knees and licking the cum on Jack's cock, then used the shower nozzle to clean my pussy. We stood under the water, hugging, until I let go and turned off the water. We emerged from the stall, dried off and put on our robes.

We went back into my room and I picked up the phone and called The Pizza Joint.

Victor answered, "This is Dana Angelo, sweetie," I said into the phone. "Bring it now," I continued, and ended the call.

I led Jack down the stairs, and got us beers. We sat on the couch and I turned on the baseball game, since I knew he liked to watch it. I never really liked baseball, but this was Jack's night. We snuggled together on the couch, in our robes, drinking beer until the doorbell rang. I got up and answered it, and as expected it was the pizza delivery guy.

"How much?" I asked.

"Nothing," he said, "Victor told me to tell you to enjoy it with your boyfriend."

"Tell Victor thanks for me," I said, giving him a $5 tip, and also letting the top of my robe open a bit to flash a bit of cleavage.

"Thanks," he said, starting at my chest.

I closed the door and brought in the food, putting it onto the coffee table in front of the TV.

"Here you go," I said, opening the pizza box.

"How did you know that sausage was my favorite?" he asked.

"You really need to remember that I make it my business to know things about people," I said, with a little annoyance in my voice before admitting, "I asked your sister." We ate the pizza and wings and watched the game, snuggling on the couch.

I was almost, if not completely, finished with my agenda for the evening. I brought the pizza box and wings container into the kitchen and returned with a can of whipped cream. I opened my robe, sat on the couch next to Jack, shook the can and sprayed rings of whipped cream on each of my breasts.

"I thought you might like some dessert," I said.

Jack didn't hesitate, and began to lick the cream off my breasts until they were slick and sticky. It felt nice, and caused my nipples to harden. I could see that Jack's hard cock was poking out of the robe.

"Now it is time for my dessert," I said, opening his robe and spraying a line of whipped cream on the top of his cock. I leaned forward, and slowly licked it off, and began giving Jack a slow blow job that brought him to a thrashing, shuddering and screaming orgasm. Afterwards, we sat, cuddling on the couch as the baseball game droned on. I looked at Jack, and he had a look of contentment and satisfaction on his face, and I smiled to myself.

After a few minutes, Jack looked at me, and, as he usually did before wanting to talk about "us" seemed to be struggling with himself. Finally, he blurted out, Dana, I want to ask you something,"

"What?" I replied.

"I want to start by telling you that today has been everything you promised and more. I will never forget it—you made me feel unbelievable, and I can't believe how much thought you gave this and the efforts you put into giving me probably the best day of my life so far."