Chapter 4: Cherry Picking

On the way back to the house she moved over really close to me and put her arms around my arm but didn't say a word. It was uncannily silent during our trip back, but that was ok. She was nervous, as any young lady would be when she knows she's only going to be a virgin for another hour or so. She was in her own thoughts and I wouldn't even attempt to venture a guess at what they might be.

I just let her be silent and made sure I was there to be held.

We pulled into the garage and let the "machine" do its work closing the door. I looked at her tenderly then leaned down and gave her a soft kiss, which was readily returned.

I followed her up the stairs into the kitchen where she turned around, threw her arms around me and held me tightly for a few moments before asking me to make her a Cuba Libre with a cherry in it.

I nodded and said, "I will certainly do that for you as soon as I get cleaned up and changed. Is that ok?"

She nodded with a smile. On her way upstairs to get changed, she said she'd meet me back down in the living room. With a smile on her face and a bounce in her step Dee disappeared quickly up the stairs.

I went up and jumped into a quick shower and put on my "best" silk boxers and my favorite Japanese silk "smoking" robe then made it back down to the kitchen to mix us up a couple drinks.

I made both drinks full strength this time, as I knew she would need to relax a bit. This was going to be her night, and I was going to make absolutely sure that it was special for her. I made sure that I dropped a cherry in her Cuba as requested.

I'd heard the shower running a bit ago and it was quite some time before I heard the door close.

I placed the full glasses on the mantle and turned to greet my young lover.

Shyly, she came slowly down the stairs towards me in the most stunning, sheer, pure white negligee, obviously one of her "secret" acquisitions at Victoria's Secret. Under that was a very small and sheer "camisole" that did nothing to hide those magnificent tits, and a pair of pure white, lacy silk panties with a cherry printed on them right in the front of her mound, just about where the little sentry would be waiting for its attention. Like the cami, the panties hid nothing.

"Oh my god Dee, You look absolutely stunning," I gasped as I was standing to meet her.

I could see the nervousness in her eyes as she looked at me for approval. I smiled at her lovingly, held my hands out to her and took a small step forward to signal her that it was ok to take my hands.

As she took my hands I could feel her quivering slightly. As bad as she wanted this to happen, she was still so nervous.

Ok. That was the first thing to settle.

I leaned over and gave her a quick peck on the lips and steered her to the couch, sat her down and handed her the drink I'd made earlier.

She took the glass from my hand, looked up with a smile and took a large drink from the glass.

I sat down next to her and pulled her to me. "You look extremely beautiful Deanna. You are dressed perfectly for the occasion." Kissing her tenderly on the forehead then on the tip of her nose, I continued with a big grin, "You remind me of a fresh piece of fruit."

That elicited a strange look from her as she scrunched up her nose and asked, "A Fresh piece of fruit?"

"Yes kitten. Ripe, and ready to eat." To which she just totally cracked up, put her arms around my neck and put a kiss on my lips to beat all then lowered her mouth to my neck and gave it a quick nip with her teeth.

Seemingly loosened up a bit, she laughed and with a loving look, whispered to me, "Honey, this cherry is ready to be eaten."

The kiss that followed was long, passionate and intense. Her tongue played tag with mine with an intensity that I had not gotten from her before. As she moaned, my right hand moved up and cupped one breast gently, which caused a very fierce moan.

I tweaked at her nipple through the negligee and cami and it immediately responded by hardening. Her tits were so responsive it was almost unnatural.

When we broke off the kiss our eyes locked on to each other and I took both breasts in my hands and kneaded them softly. She moved her arms up around my neck even higher to give me more unrestricted access to her luscious orbs.

One of her hands reached down and wrapped around my rigid cock and she moaned loudly, and once again, with a sparkle in her eyes, asked me her magic question, "Is this for me?"

I looked deeply into her eyes and with a smile, gave her my "stock" answer; "It's yours if you want it my love."

"Oh Tommy, I want it. I want it so bad, I can't stand it anymore."

I stood up from the love seat, took her hands in mine and lifted her to her feet. She gave me a questioning look when I bent over, lifted her up, and began to carry her towards the bedroom. She buried her face in the crook of my neck and nibbled lightly, kissed and gently licked as we made our way up the stairs. She lifted her head slightly and whispered quietly into my ear, "I love you so much."

As I made it to the door and turned to enter, I noted that she had already pulled the blankets down and laid down a silk "virgin pad" to protect the bedding and mattress from any blood that may "leak. Another Victoria's Secret surprise."

She whispered again, "I love you so much Tommy. Please, make love to me? Please."

"I love you too honey, and it will be my pleasure to share my love with you."

I gently set her down on the bed centered on the silk pad that she'd put down and joined her in the bed.

Our eyes met quickly and the love being expressed with just our eyes was intense. I reached down and slowly and deliberately started to remove her negligee. She twisted a bit so that I could take it from the bed and put it on the chair next to the bed. I sensually took my hands and caressed her face, then down to her breasts and slowly untied the two bows on the front of the cami and pulled it away from her body leaving her nude except for those incredibly sexy pure white, silk panties she had put on.

She looked up at me and reached over to pull off my boxers as I put my mouth on first one breast then the other not leaving one to be neglected. I felt her hand circling my cock as she gently stroked it.

With her other arm she pulled me down to the bed to be right beside her when I reached to slowly, seductively, remove her panties, her hands met mine to symbolically give her sex to me.

We pushed them down off of her butt and hips as she raised them slightly to assist with the removal of the last protection her sex had for this evening.

She let out a loud moan as one hand cupped her mound and slit while it was moving back up from its pleasant task of removing the panties.

With both of her hands, she took my face, kissed me deeply, and pushed me over onto my back. She immediately started moving her face down my chest over my belly and on to my cock. Her hand had been keeping it warm for her hot moist mouth, and she took the tip of my cock in her mouth, licked and sucked it like a woman that had been giving head for years. I moaned loudly as she licked from the base to the tip and sucked my balls so softly into her mouth while stroking gently. She settled down to suck me dry. Her head bobbing up and down, twisting around, and generally trying to pull as much sperm from my balls as she could.

"Oh shit honey, I'm going to come," I gasped out to her.

She moved her head up so that the head of my cock was just inside her mouth and started moving her tongue around until I unceremoniously shot my load into her beautiful mouth. She didn't slop a drop. She wolfed it all and continued to suck me until it was all cleaned up, starting to get hard again.

She took her mouth off my cock and with a big grin, told me, "You'll be in my pussy for a good long time after that load."

As she moved up towards my face again, she whispered to me, "I want you inside me Tommy."

We kissed very passionately as she maneuvered herself on to her back and pulled me on top of her.

As our kiss ended, I started sliding down her body stopping momentarily to partake of the dual orbs that were bumps on the path to her nether world.

I used my mouth, teeth, tongue fingers and anything else I could think of to manipulate all parts of her body as my mouth stopped once again at her belly button and played for a short time pulling some giggles out of her.

My face got down to those soft downy hairs that were trying to protect her mound, and I reveled in their feel before moving my tongue the length of her tight virgin slit. Her lips were swelling noticeably, but still tight together protecting the inner sanctum and the entrance to the "Promised Land". The primal odor, her taste, everything about this pussy was heavenly.

I continued working on her sex, parting the outer lips and running my tongue up and down the inner spaces inserting at the bottom, teasing at the top.

She was writhing, squirming, and bucking like crazy as I moved her up towards that final climax before giving her the filled feeling she was craving. As soon as I thought she was just there, I moved my tongue away to let that feeling marinade a few seconds before I went back to work on that little nubbin that kept itself available for the entire show. I put my tongue in her pussy hole as far as I could and wiggled my nose against her clitty, then moved my tongue up to the bud, put my mouth around it and sucked and licked until she exploded. Her legs clamped around my head, her hips were moving in directions I could never have predicted and her screams were heaven to my ears. Her orgasm took her away completely.

Her legs relaxed on my head and I went back to gently moving my tongue around her pussy making sure I was clear of her clit.

As her spasms started to lessen, I began my journey back up to her face, of course stopping at her mounds for a few additional licks and nibbles.

By the time I was able to look into her eyes, she was nearly "conscious" again and weakly smiled at me, but was still unable to say anything.

I lowered my lips to hers and kissed her more passionately than I ever had before. She returned the kiss in earnest and licked her juices off my face with relish.

"That's what I taste like?" she asked with a grin.

"Yes it is."

"I like that. I don't taste bad at all," she observed breathlessly.

"No kitten, you taste delicious. The best, the sweetest pussy ever."

We held each other side by side allowing her to recover from the massive orgasm she'd just had.

Our eyes were locked on to each other's and we were gently giving peck kisses all over each other's face.

The entire time Deanna had my cock in her hand, gently stroking me to make sure I got as rigid as possible. We both knew the time was near.

I started kissing her with more intensity as I started to move my body up over hers. I had told her that it might be easier if she were on top the first time so she could control the penetration, but she wanted it in the traditional "missionary" position. "I want you to take what I'm giving sweetie. I want to feel your love enter me while I'm giving you mine," she said quietly, softly running her hands through my hair.

I had already resolved to go very slowly and easy for her. What I couldn't control was her exuberance, so I had to be ready for that.

As I moved up over her she opened her legs for me and put her knees around my hips as I rubbed my cock through her slot paying close attention to the little hard spot at the top that was rubbing the bottom.

Each time I stroked forward she moaned and her breathing was getting faster and deeper as she moved closer and closer to another orgasm.

The lust in her eyes was so incredibly intense while she let her body be ready for the ultimate expression of her love.

When her orgasm started she twitched almost uncontrollably as I let my cock slip down her slit until it was right at her opening. I applied a little pressure to see how it was going to go and as I pressed, her outer lips just parted for my cock and it found itself pressing at the entrance to her vagina.

Our eyes met and stayed, her hands came up to each side of my face holding me gently, and lifting her lips to meet mine, she whispered to me, "Do it Tommy. Now please. I want you inside me so bad."

I pressed a little harder and could feel her start to push against me.

POP! The head of my cock was firmly inside the entrance to her vagina.

Her eyes got a bit larger as she gasped and moaned at the same time.

"Oh god Tommy. That feels so good. Oh my god, please give it all to me."

"Slowly Deanna. Please baby; let's take it slow. I felt your cherry give way already. Let me try to stretch you a little before I push more. It may not hurt quite as badly if we just stretch you through it."

"Oh shit Tommy, it feels wonderful so far, and I know you didn't want to hurt me, but I was ready for it. I wanted the pain; it's telling me I'm truly your woman. Please, just push in and stop so I can get used to how it feels."

During her "speech" I had been pressing in against the muscles surrounding the path and it didn't feel all that formidable, so as she was finishing her plea, I pressed a little harder and with a small lurch I pushed about an inch further in.

"Oompf. Mfhgg," came out of her mouth, as her eyes got bigger. And a very quick, "owww." Her cherry apparently hadn't ripped completely with the first push.

I stopped moving and didn't move a muscle as I looked into her face for any sign of the need to withdraw and let things settle. I didn't see any. What I did see was a look of inquisitive pleasure. She didn't know whether she really liked it a lot or whether it was a bit more than she expected, but there was no indication that she wanted to change any position, so I just maintained where I was and waited for her. You could tell that she was trying to get used to the feel of having something inside her tight opening and I could feel her manipulating her muscles around my cock to test her ability to squeeze. She seemed to know what it was doing to me already, so she got this evil grin on her face as I moaned through closed eyes.

There was a small giggle from below me, "Are you having a little problem Thomas?"

I chuckled at her, "You little she devil. You just let me know when it's ok to move again and I will continue to fill you completely."

"Oh god, thank you. I know you are trying not to hurt me baby and I love you for that. So far, just the feeling of you entering has been so special to me – just knowing that I can give you my love totally and completely means so much to me. And next time it will be without any pain at all!"

"Honey, if it takes all night to finish what we've started that is the way it is," I whispered, but what I didn't tell her was that taking all night would be ok with me.

The feeling of her tight entrance and her muscle experiments was something I never wanted to end. But I also know that this was only the beginning.

I would have this young woman as long as she would have me. I didn't intend on ever letting go, and I'm sure Tara would not object. I felt for Tara because I wanted her as well, but not in the same way as her daughter. It sounded as though as far as Deanna was concerned it would be ok to "share" as long as she was my main squeeze. If Tara was willing to do that, I wouldn't object at all, but that was going to be between mother and daughter.

Deanna started to wiggle slightly to see if she was ready for more movement and I could see the small wince as the torn skin caused her discomfort, but she tried her best to hide any adverse reaction knowing that it would inhibit my continuation. "Please push in a little more and stop," she said quietly. "I think if we just do it a little at a time it will work better, let me adjust to being stretched and filled. God, I love this feeling, Tommy, so don't be worried that I'm not comfortable. I can't wait for that little sting to heal so it'll just be getting my pussy used to having your cock inside."

I pushed in gently about another half inch or so causing Deanna to moan loudly and gasp out, "Oh gawd that's good. Oh shit Tommy, I can't believe this."

"Honey. What I'd like to do is move back and forth, in and out a little to make sure I stay lubricated with your oils so we'll stay slippery and will probably make it much easier for you. When I do move like that it may push in a bit when I stroke back inward so if it gets uncomfortable please tell me to stop or slow down or whatever you'd like me to do."

By doing it this way I'd penetrate more slowly and cleanly, but if I accidentally got pushing in too far too fast she can slow me down or stop me. If I do this right and pause at the proper spots and push gently I'll be all the way into her before long and it will cause the least amount of discomfort. I know that she'll have some level of discomfort anyway just because there's never been anything in her this deep before. Her pussy is going to need to stretch to fit. My cock isn't a monster, which unlike some fellows I know it isn't a big deal to me. Ha. Pun intended!

I've never had complaints about the utilization and I don't think Deanna will have any complaints either. It should be fairly easy for her to stretch adequately to accommodate the "medium" size.

"That sounds so good Tommy. It sure feels great so far, but it is a weird feeling since there's never been anything in that far before, not even fingers!"

"You'll get used to it and after this time it should never hurt like this time. I'm really sorry that it hurt at all but for some reason God made it so that a woman's first time is painful. It sure would have been a whole lot easier on females if that cherry wasn't there."

"Yeah. I guess I could have broken it before. Some of my girlfriends used their hairbrush to break it, but I wanted to give it to my man. If I hadn't already known who I wanted to give it to, I may have broken it myself, but that hymen was for you and nobody else!"