Chapter 22

When school ended, Debbie met me at my car, a big smile on her face and she hugged me and gave me a toe curler of a kiss. She was in her regular clothes, a pair of surfer shorts, a polo shirt and an industrial strength bra, evidently!

I had warned Dean and Deb that I was bringing a girl home, but not who. It didn’t matter they were both out of the house, though I wasn’t sure where. To be safe, I reset the alarm once we were inside.

I got us some sodas and, when I turned to offer one to Deb, I just caught sight of her turning the corner on the stairs, heading up to my room.

I followed along behind her, taking my time and enjoying the tension. When I got to my room, the bathroom door was closed and I could hear her inside.

I set the drinks down on the bedside tables, kicked off my shoes and socks, and kicked back on the bed, my back against the headboard.

When the bathroom door was opened, Debbie stood there in the outfit she had worn at lunch. She had ditched her bra because her nipples were at attention again, and even from where she stood, I could smell her excitement. I went from interested to hard as steel in just seconds.

Debbie strutted across the room, stopping only to kick off the high heels she must have had hidden in her bag. When she knelt on the bed, her skirt rode up for just a second and there was no way she was wearing underwear. The flash of pink I saw was pure Debbie.

“You said you would make me scream your name, Jack. Did you mean that or was it just bragging?” Debbie asked, biting her lip and looking up at me through her bangs.

I just crooked my finger and watched her crawl across the mattress, her breasts swaying in her top and her hips performing a counterpoint. When she was close enough, I reached out and lifted her chin, leaning forward to capture her lips with my own.

She came willingly into my arms, our lips never parting, and within a moment we were both without our clothes, intertwined on the bedspread.

I had no idea she was so fit. This girl worked out seriously and as I ran my hands down her arms, down her sides, across that sexy stomach and then flaring out to her hips, I was memorizing every inch of her flesh.

When I finally got where I was going, that luscious, oh-so-sexy ass, I was in heaven! It was so round and so hard, so firm and smooth. When I broke away from her lips, gasping, I flipped her face down and took my time tracing the muscles of her back, bypassing her butt and loving on her legs. Her thighs and calves were works of art, a canvas of rippling muscle. Even her feet, not something I normally cared much about, were smooth and sexy.

It was all foreplay to me though, I wanted to worship that ass.

I touched, tasted, licked and caressed every square inch of that luscious booty. I ran my tongue down the valley between her cheeks and dipped the tip of my tongue into her starfish, reveling in the moans and the gush of fluid between her hard thighs.

When I urged her to turn over, I moved back up and started over. I caressed her ears, traced the muscles on her neck to the hollow of her throat and felt the pulse against my tongue. Down further to her breasts, sitting so high and firm on her chest.

Her nipples were even more glorious in person, without any material between them and me. They were long and thick, every bit of three-quarters of an inch, and begged to be sucked. When I wrapped my lips around one, lashing it with my tongue while my fingers went to work on its twin, Debbie surged beneath me as she came again, her pelvis lifted up off the bed and thrusting, as if searching for what I could give.

Instead, I kissed my way south, spending some time just appreciating her sculpted abs. They were simply amazing!

When I finally got to her center, with just a small patch of hair over her clit, the rest shaved bare, I buried my face and breathed deeply, filling my lungs with her scent until that was all I could smell.

Her clit was not large, but it was already peeking out from its hiding place, waiting for the touch of a hand, a kiss, a lick. Debbie’s clit was way too sensitive to handle roughly like I would with Cam, but I found that if I ran my tongue over the hood and just underneath her clit, it was like prodding her with a cattle prod. When my fingers found her g-spot and I began teasing it as I tortured her clit?

All I can say is that I am so glad she had her thighs clamped on my head or my ears would have been damaged!

When she pushed at my head, her legs trying to close and push me away, I moved up and held her, stroking her back and that sexy, sexy ass while she recovered.

“Jack, oh you evil fucker. Come here, big boy, give me what I was playing with yesterday. Let me see that cock.” she growled, pushing me over on to my back. She slid down, taking my cock in her hand and began teasing me.

She would lick up one side and down the other, then take just the head into her mouth while her hand stroked me.

“Is this okay, Jack? I have only played with two and that was my freshman year. Tell me if I am doing something wrong, okay?” With that, she took as much as she could in her mouth and let her tongue lash the head and shaft as she stroked me. I hadn’t had anyone touch me ten months and I was ready to blow!

“Debbie, it has been a long time for me, you need to stop before...” and that was as far as I got. She seemed to think that meant GO FASTER!

Before I could say another word, I was shooting everything I had into her waiting, suckling mouth. She didn’t miss a drop, even sitting up and licking her lips, a self-satisfied smile on her face, when she was done cleaning me up.

“That was more fun than I thought it would be. Not as tasty as eating pussy, but not as bad as I feared. How long until you can get it up again, Jack?”

I just stared at her. Where was the timid girl that was here earlier?

“Maybe if I give you a little visual stimulation, Jack? I hear guys are visual creatures.” Debbie said with a smile, settling back on her heels where she was kneeling, one hand idly toying with her nipples. The other hand slid down, caressing her stomach first before dipping lower, to dive into her wet pussy. She pulled her hand back up and I could see how wet her fingers were when she stuck them in her mouth, humming happily as she cleaned them off.

Back they went, into her snatch again, rubbing and tugging, plunging and swirling. Then she did something that made my cock spring back faster than I thought possible

“You seemed very interested in my poor butt, Jack. Do you like this? Are you an ass man, Jack?” she turned on her knees, her legs spread and her ass in the air. Her pussy was wet and open to my gaze, but so was her pucker. She dipped two fingers into her pussy and used them to wet her pucker, slowly pushing one inside. Then, with almost no hesitation, she pushed a second one inside and began slowly fucking her own ass with her fingers.

“Oh my, Jack, that feels better than I would have thought. I loved having my ass licked, and you made me cum doing that, but I never let anyone put something inside of me. Would you like that, Jack? Would you like to take my last cherry? Do you want to fuck my tight, virgin ass, Jack?”

Oh my god, what this woman was doing to me! Yes, yes yes yes. I could almost cum just watching her!

“Jack, if you fuck me good, if you make me cum on your hard cock, I will let you take my last cherry.” Debbie said seductively. “It won’t be easy, Jack.” she continued, rolling over on to her back again and spreading her legs, her hands calling to me.

“I have had tongues and fingers, toys that were pencil sized and toys that would blow your mind. I even had a little tiny thing, a girl who was fifteen but looked nine, put her whole hand in there, Jack. She fisted me, Jack, and I came all over her arm.”

I moved closer, lowering my body over hers and dipping my head to suck on a nipple.

When she reached down and pulled, I resisted, but barely. “Debbie, birth control?”

“On the pill, Jack, since I was thirteen. Now are you going to fuck me and make me cum or not? I thought I would never invite another guy into my pussy, Jack, but you make me so hot. Fuck me, Jack, fuck me!”

She had bragged about having huge toys and even a girl’s fist, but she was damn tight! I had to work my way in slowly and, when I reached bottom, I stopped until she started to move under me. There was still an inch or so of cock left, but I didn’t want to start banging on her cervix and hurt her, so I took it slow.

Cam had shown me how angle made all the difference, so I gathered Debbie’s legs up until they were pointing at the ceiling, then bent forward until her pelvis raised up off the mattress. With that angle, I could thrust up so the head of my cock rubbed against the G-Spot I found earlier and when I did, Debbie gasped and her eyes shut tightly.

She began to move her hips in time with my thrusts, meeting me on the in stroke and squeezing me tightly as I pulled out. I was now completely buried in her and my cock was rubbing her just right on the way in and on the way out.

Debbie was climbing quickly, her breath coming harder and faster. Both hands were on her own breasts, pulling and tugging, twisting her nipples almost cruelly!

Faster I stroked, harder against that spot, then smoothly until buried. Again, and again, when her hips came up, her head went back and her hands were like claws, locking on to her ankles, trying to prolong that moment as her pussy clamped down on me so tightly I couldn’t move if I had wanted to.

Instead, I kept bumping her with my hips, forcing my cock, locked in her pussy, to move her flesh around and rub her clit. Then, with a high-pitched whine that was almost too high for me to even hear, she collapsed and went limp.

She was staring up at me, a big smile on her face. “That was fantastic, Jack! I came hard and it was oh so fucking good! Do it, Jack. Give me that cock. Stick it in my pooper, Jack, you deserve it. Take my cherry!” Debbie was almost chanting, her pussy pulsing around my cock.

Without waiting, I just reached down and lowered the head, letting it slide, wet and slippery with her juices, until it lodged at her pucker. A little push and pop! The head went in and Debbie gasped.

I watched her face, gauging her interest, her pain level. She looked surprised, mostly, and I could feel her hips moving a little. Testing, feeling, probing ... then she shifted and another inch went in. Her eyes opened even wider and one hand crept down to start rubbing against her clit.

“Do it Jack. Go slow but do it. I think I am going to like this! It is so ... dirty, and so shameful, but it feels good in there, it feels so full, Jack.”

When I hit bottom, my hips up against her luscious ass, I had to really work to keep from cumming right there. I was in her ass!

“Jack, what are you waiting for? Fuck me, Jack. Fuck my ass. Make me your little butt slut.” Debbie said, giggling. That giggle did wonderful things to the muscles in her bowel! I pulled back until just the head was lodged inside, Debbie growling and moaning. Then I thrust, slow but steady until I was buried. I began to pick up the pace. Half a dozen, ten, a dozen, at eighteen strokes, I know because I was counting to try and hold off my orgasm, at eighteen I lost it and everything inside my body seemed to pour out through my cock and coat the inside of her ass, spurting deep into her bowels.

It. Was. Glorious.

When we had cleaned up a bit, and pulled the wet comforter off the bed, Debbie curled up at my side and laid her head on my chest.

“Jack, you know this is ... just a thing, right? I like you, and you are sexy as hell. You are great in the sack, but I am definitely a lover of women. I mean, romantically. I would totally have you get me pregnant someday, but I will be marrying a woman.” Her voice was soft and a little hesitant.

“Don’t worry, Debbie. I am a bit broken right now. Cam walked out and you are the first woman I have been with since. I am not going to fall madly in love and start stalking you.”

There was silence for a moment, then a giggle. “Hey, a girl wants to be wanted.”

“We could hook up though. You know, until the end of the year anyway, I know you are doing that macho man motorcycle trip and everything.” she continued, playing with my nipple.

“I think I would like that, if you think we can play regularly and still be friends. If not, I would rather have a friend.” I told her, meaning it.

“Should I tell my mom that I decided I like dick? I mean, not love, love, but like.” She asked, snorting when she tried not to laugh.

“I think I would just let it go. She means well, I am sure. It is good though, that Alan is not gay. Unless Pam is trans and I just never knew. She’s pretty cute for a guy.”

Now Debbie was full out laughing. “I wish, then I might have gotten further with her. She is definitely a woman and she says Alan can lick her tonsils, from the bottom. If the whole incest thing was not so icky, that sounds like fun.”

Now it was my turn to laugh. “Incest, you mean Wincest!”

“No memes when we are naked in bed. Bad Jack, Bad! Now you owe me another orgasm before you take me home.”

“Oh no, however will I go on.” I deadpanned, reaching down to tickle her clit with a finger as I licked her nipple. “Woe is me!”

I got her home on time, just before midnight, and spent about ten minutes just chatting with her folks. It was a good thing we were playing by the rules, sort of, since they were supposed to be out of town! Plans had changed and they were leaving tomorrow. Alan and Debbie were good kids and they trust them to be alone precisely because they knew the kids would mind the rules laid down.

I guess I am glad that there were no clearly defined rules about sex! It was strange, I fully expected to be wracked with guilt, torn up over having what was, for all intents, meaningless sex. I mean, we were not a couple and were not going to be a couple, so it was just fuck buddies, right? After all my hang-ups, and the pain my split with Cam had caused, I didn’t expect it to be that easy.

If I had known, perhaps Sarah and I might have lasted a bit longer. Then again, if she had been fucking someone else while we were dating, I would have been even more upset if we had been intimate.

Debbie and I managed to get together only one more time between that Friday and Prom, and it had been a pretty quick sixty-nine followed by some fun, but vanilla, shower sex. Prom was shaping up to be a big deal. Not for me, necessarily, but for Debbie. As an out lesbian during her whole high school time, she had expected to go to this little splinter prom for alternate lifestyle types. It would have been mostly goth and emo kids who liked to pretend they were outcasts though.

Now that she was going to the real prom, she was as giddy as, well, a school girl!

I decided to make this a huge thing and spent some money to make the whole experience even nicer. First, I took Debbie, Alan and Pam with me to Miami and had the girls fitted with custom made gowns and got Alan and me into real tuxedos. Then, though this was secret for now, I made arrangements so that we would be picked up in a huge, neon pink, stretch H1 Hummer limousine.

After the Prom, I had it set up so we could have a nice meal on the beach, complete with white table cloths, real crystal and champagne. From there, since there wasn’t any place on Key West that matched what I had pictured when it comes to high-class hotels like mine in San Antonio, we would go to my house.

My Deb had taken over the downstairs guest bedroom as her own, so I made sure there was an upstairs guest room ready with everything from fluffy robes to flavored condoms. I think Alan and Pam would have fun.

Prom went like clockwork. Debbie, Alan and Pam trusted me enough to be ready when the limo pulled up to the twins’ house. Their parents were rolling on the floor, laughing at the expressions of the three kids and the photographer, rented paparazzi, caught it all on film. Or digital. Whatever.

We let the parents get their own shots, but I assured them that the photogs would be following up all night, at least until the after-party, and I would give them a set of the pictures. I assured Pam’s of the same when we stopped by so her mom could get some pictures, and a look at the rest of us.

We pulled up to the gymnasium in style, drawing every eye in the parking lot and even a bunch of kids from inside, coming back out to see the spectacle when told about it by their classmates.

The two photogs I had hired made it good, snapping pictures fast and furious as we walked the red carpet. The girls were smiling so widely that I feared their faces would be sore tomorrow! Heck, Alan wasn’t much better and, I admit, I was having fun with this.

Inside, the only dark spot on an otherwise glorious evening is when some dick, obviously sipping on smuggled alcohol, made a play for Debbie and wouldn’t take no for an answer. When he grabbed her breast, I am afraid I lost my temper.

When I stepped forward and grabbed his hand, the one that had touched Debbie inappropriately, I made sure I had a good grip on the hand itself, the thumb tucked into the palm and causing him no little amount of discomfort.

“No means no, asshole, and if you ever touch a girl against her will again, I will do more than break your wrist.” I growled at him.

“You didn’t break my wrist, fucker, you are just holding my hand like a faggot!” He replied, the alcohol making him feel brave.

I reached down with my other hand and grasped his wrist, then twisted hard and fast. The crackling noise, kind of like cracking your knuckles except angrier, was shockingly loud. The twist movement tore several ligaments, freed a couple of tendons and separated the Carpal bones from the bones of the Ulna and Radius. The pain must have been considerable because his eyes just rolled up in his head and he passed out.

Alan and I caught him under his arms and helped him over to where a couple of the chaperons were standing.

“Excuse me, but this guy smells of alcohol and he passed out over there. He landed on his wrist, so he might have hurt himself.” Alan offered, sneaking a quick look at me. I just grinned and nodded.

The teachers were scandalized, of course, and one hurried off to get help. Alan and I laid the kid out, crossing his arms over his chest, and then faced back into the crowd.

I earned myself a peck on the cheek from Pam and a toe-curler from Debbie for that, and the dance continued flawlessly.

Dinner on the beach was nice! There was just a faint breeze and the tiki torches and candles that lit our little romantic dinner were a nice touch. In addition to the four-seat table, they had erected bamboo privacy screens to give us the feel that we were all alone on the beach, even if there were some couples snogging down the shore a bit.

Back at the house, Dean surprised all of us, me included, by meeting us at the door in his own penguin suit. He gave me a quick wink and bowed to us as we got out of the hummer.

“The McCoy party, I assume? I am Jeeves, your major domo for the evening. We have prepared a light snack and, of course, champagne for our most distinguished guests. If you would be so kind as to follow me?” he said brightly, his fake British accent was so cheesy that it warped back around to cool again!

Inside, he handed Alan and I silver trays that held small bottles of champagne, glasses, plates with some chocolate covered strawberries and grapes on them, and then showed us to our rooms.

“If that will be all, sirs? I am afraid I am going off duty and will not be in the house if you find you need more refreshments, but the cooler downstairs is fully stocked.” Dean said, bowing again before heading downstairs.

Just a minute or two later, we were alone in the house! Well, alone together, with another couple, or ... you know what, close enough with the doors closed.

Debbie and I tried just about everything we could think of, and a few that I had never even considered, finishing just in time to sit out on the back deck, in only our robes, to watch the sun rise. It was glorious ... exhausting, but glorious.

We were sitting on the patio, sipping coffee and leaning against one another, when Debbie asked something odd.

“Will you sing for me again?” she asked, her eyes never leaving the glorious vision of the sun just peeking over the horizon.

“Sing? Again? What are you talking about? I don’t sing, and I have never sung for you.” I asked, confused.

Debbie lifted her head and turned to meet my eyes, smiling softly. “You sing. You sang when we danced last night. Not all of the times, just once or twice when the music was soft. You have a beautiful voice.”

I had not! I never sing where people can hear me! In the shower? Yeah, okay, but who doesn’t? The acoustics are awesome. But ever since I was a kid, I couldn’t carry a tune if I had a bucket. I had liked drama club when I was in middle school, loving the whole ‘being someone else’ aspect of taking on a character, and I was pretty damn good! The drama teacher always wanted me to take on the harder roles.

But when we did our yearly musical, and I tried out, the horrified faces on the other students and the pale, shocked face of both the drama teacher and the music teacher ... well, that was all I needed to know. Ms. Underwood, the drama teacher, gave me a hug and told me that it was okay not to be great at everything. The music teacher wouldn’t even meet my eye!

Now Debbie said I was singing to her, and I know, I know I wasn’t. I wouldn’t dare!

“Debbie, sweetie, I don’t sing. I am tone deaf or something. I once made a music teacher physically ill when I sang in front of her. I. Do. Not. Sing.” I told her, making it perfectly clear.

Debbie laughed. She laughed at me! It started as a giggle, sure, all lady like and proper, but before I knew it she was roaring and throwing her head back, rocking as she howled out her amusement for the whole world to hear.

When she calmed down, taking the napkin I gave her and wiping her eyes, she turned sideways, her robe gaping a bit and distracting me with glimpses of her toned body.

“Jack, baby, whether you realize it or not, or thought it was just in your head, you sang last night. You sang to me and I loved it. Your voice made me want to pull you out of that dance and do you in the bushes! I am not lying and I am not joking, your voice made me seriously wet.”

She was serious. I had known Debbie for three years now, been friends with her the whole time and I knew when she was serious.

“You did, you know. You sang when you danced with me, too. She’s right. You have a voice made to seduce girls out of their panties.” Pam said, coming outside with her own cup of coffee, hand in hand with Alan. They were just in robes too!

I looked over at Alan and he just shrugged. With a grin, he guided Pam to one of the other couches. “Don’t look at me dude, we never danced.” he said smugly.

“And what song did I supposedly sing?” I asked, not caring, really, but stalling. This was just too weird.

“You sang Radioactive by Imagine Dragons to me.” Pam chirped, humming a bit.

“Aerosmith, I don’t want to miss a thing.” Debbie said definitively. “Also, Wonderful Tonight by Eric Clapton. That one got me going ... I seriously considered blowing you back at the table when that song was done.”

“Eeewww! TMI, Debbie, for god ‘s sake!” Alan cried, then laughed at Debbie’s expression.

“Oh, and I saw you mouthing the words to that LMFAO song, Sexy and I know it!” Debbie said suddenly, sitting up straight. “You were dancing with Mrs. King. We were all laughing our asses off when you went and asked the principal to dance, like a suck up, then that song came on! It was fucking legendary! Everyone at the school will be talking about that dance tomorrow.”

I just buried my face in my hands. All of the songs they had mentioned were songs I really liked, songs I sang in the shower when I was sure no one was upstairs to hear me. Had I really sung in public?

“Okay, maybe. Maybe I sang, but I know, I am one thousand percent certain that I can’t carry a tune. I tried out for a musical in eighth grade and made my music teacher ill. The drama teacher, who loved me and always cast me in the best roles, told me to stick to acting and leave musical theater alone.” I told them, feeling better. Those memories, while painful, were vindicating!

None of them seemed convinced at all.

“Jack, you were what, thirteen? You had barely started puberty, if you had started, and your voice back then was nothing like what it is now.” Pam said reasonably.

“A tone-deaf ear doesn’t get fixed during puberty, Pam.”

“Whatever. Let me tell you, you were spot on and you sounded fantastic last night. If I wasn’t hopeless about this geek here, I’d let you sing me out of my thong.” Pam joked, reaching inside Alan’s robes to run her hand over his abdomen ... and lower.

Alan looked surprised, then a bit smug when he had finished parsing her sentence.

“So, anyone up for breakfast? I think we should pile in the car and hit up IHOP. I am seriously craving some pancakes!” I asked, giving Debbie a quick kiss and standing up.

I guess they decided that pancakes were more attractive than arguing with me about my supposedly singing to them last night. I am sure they heard what they wanted to hear and nothing close to reality!

The rest of the school year was definitely an anti-climax, with finals and then just marking time until we could graduate. It was a sad time too. I had made some good friends and we were scattering all over for college. There was a decent chance I wouldn’t ever see them again, but I tried to stack the odds in my favor.

I made sure they all knew that I was keeping the house here and that I would be back to visit. My phone and email would remain the same and I told them to feel free to call me if they ever needed me for anything. I wasn’t sure they would, but I could hope.

I didn’t actually stick around for graduation. I just told the school where to send my paperwork, citing a move to Austin as the reason I wouldn’t be walking the stage in June. It was true, the move part, I mean, but it was mostly because ... fuck that noise. Waiting for hours just to walk across a stage and get a fake scroll? Totally not my idea of fun. I had no family to appease and I had already said my goodbyes to my friends.

Instead, after the last day of school, I left with the E², headed for Galveston. I would sail straight across then fly back again. The E² would be stored inside a climate-controlled warehouse, her engines preserved, her tanks dried out. The Emancipation Key, however, I decided to leave at the house in Key West. I would lift it out of the water and pay a local firm to pickle it. Luis would be watching the house when I wasn’t around so, barring a Cat 5 hurricane, she should be good.

Deb went with me to drop off the E² while Dean got things going at home. We made the trip across the gulf in three pretty relaxed days and turned her over, minus the guns, cash, gold and any personal paperwork I had in the safes. All of that I had left home. Well, except for our travelling guns, of course. No sense in being silly.

We flew back and Dean picked us up, filling me in on what he had arranged while I was gone. The rental bike Deb had ordered had come in, and she was excited to see it. He had arranged for a service to pick up his truck tomorrow by lunch time and had already packed the two lowered, stretched and souped-up Rucki in the back, covering them with the aluminum, rollout tonneau cover.

Deb didn’t have a vehicle to transport yet, but I had given Deb the same deal I gave Dean. I would pay half for any car she wanted and it would be hers, in her name. Or I would pay the whole price and the vehicle would be registered to the trust, insured by the trust, and would remain the property of the trust even though she would be the primary driver.

She had chosen the same route Dean took, ordering a brand-new BMW M4, but it would take six weeks to be shipped to the US and she would take delivery in Austin. In the meantime, and so she could ride with us on this trip, we had arranged a rental Trike, a new Harley Davidson three-wheeler, but had to get that shipped from up north since no one in Florida had one for rent.

The house was about all closed up. We had left one gun safe with equipment in it, and some well-hidden cash and gold too, but most of the guns and currency had been shipped already. We had insured and bonded carriers taking our gear to Austin and storing it until we arrived.

Over the last two months, Deb and Dean had taken several trips to Austin to make sure the installation of the new security system in both apartments was progressing as planned. They had the new gun safes installed, a walk-in closet in the master bedroom transformed into a safe room. There were small, biometric safes in each room as well as a hidden safe in the pantry for papers and gold.