Unfinished Family Business Ch. 02

Mom gave me a hug and a peck on the cheek. "I'll be ready in a few minutes, honey, I just need to shower. I worked up a quite a sweat with Martin today." As I hugged her I could feel how damp her little tennis outfit was, but even all sweaty Mom still looked fantastic. The snug outfit, with it's short skirt and V-neck, really showed off just how in shape she did keep herself, and with her tanned, firm legs I had to agree with Martin, she didn't look old enough to be my mother.

While Mom freshened up I grabbed a beer at the clubhouse bar and watched a little ESPN on one of the televisions. It only took a remarkably short time for Mom to pull herself together. She emerged from the women's locker room in a pink sleeveless blouse and black skirt that demurely stayed close to the knee. Although the outfit was conservative she looked sexy.

"Are you ready for me?" Mom asked.

She had no idea. "Always. May I escort you to lunch, madam?"

"Of course, young man," Mom giggled. She linked her arm in mine and we walked back to the manor house where a table awaited us on the back porch. It was a gorgeous spring day and perfect for an outdoor lunch. Mom ordered a Bloody Mary and asked how things were going with the business, so I explained the problems I was running into on the Braddock project. She nodded sympathetically, which I'm sure is a move she perfected with my father, and seemed genuinely surprised when I asked her advice, something I'm sure Dad never did with business matters. But Mom is a very intelligent woman and had shown a definite talent for organization in her charity work, so I valued her opinion. She seemed to enjoy my including her in the workings of the business.

I mentioned that I'd run into Diana and Mom asked if she's spoken to Gwen. It hadn't come up, but I lied to Mom and told her no. I could tell she was still holding out hope that my sister would come home for Spring Break and decided to try and call Gwen again when I returned to work.

It was difficult to get out of the office on time the following night to meet Diana, but I needed the break badly. Around Diana I knew I could be goofy and flirty and forget about all the responsibility weighing me down. I took the Jag roadster instead of the Range Rover, as I knew she would enjoy riding with the top down. When I picked her up, Diana's parents commented on how nice it was to see me and I could tell they were glad that a responsible young man was there to pick up their daughter instead of the type of guy she usually brought home. And seeing as how I was her best friend's older brother I'm sure it didn't occur to them that anything untoward could happen.

We ate at a local café that was nice enough that I wouldn't be out of place in my work clothes, but wasn't too stuffy to have fun either. Later in the evening a three-piece band went on, but until then we'd be able to talk, though based on the way Diana was dressed I didn't think talking was the only thing on her mind. She was wearing skintight black pants and a tight fitted shirt, which closed with hook-and-eye closures instead of buttons. It didn't quite meet her pants, showing her sexy, soft belly, and was left open halfway down her chest to show off a lacy red camisole, which struggled to contain her chest. You had to hand it to the girl, she knew how to make the most of her assets. When we walked into the café I could see several heads turn to follow her progress and it earned one guy an icy stare from his wife.

While I paced myself throughout dinner because I was driving, Diana didn't have any such inhibition and got a nice buzz on before dinner even arrived. She had blackened fish with dirty rice while I dined on a nice big medium rare steak.

"How is your Dad doing?"

"The same as before. The doctor's don't think it's likely anything is going to change. I know it's too soon, but at some point I'm going to have to talk to my mother about taking him off the machines."

Diana reached across the table and took my hand. "I'm sorry. That's not going to be an easy conversation to have."

"Tell me about it. I really try not to even think about it, really. How do you begin to make a decision like that? I don't think I'm equipped to make life and death decisions." Especially when I was responsible for his condition in the first place.

"Your mom will have to decide, but I'm sure it will be easier for her with you there to lean on."

"I hope so. I'd do anything for her. I just wish Gwen were here too. It would really help Mom. Have you talked to her lately?"

"A couple weeks ago, but when she gets on the phone she doesn't say much. This has been so hard on her. I know she was like your dad's little princess, but I had no idea they were so close. I don't quite understand why she's pulled away so much."

And I wish I could tell you, I thought. "I think part of her staying away is because of me."

"She's never said that. Did you guys have a fight before she left?"

"No, nothing like that, but maybe she just can't cope with what happened – y'know, with us."

"Tony, don't put this on yourself. I know Gwen very, very well, and believe me, that was something she wanted. She had a crush on you back when you guys were younger and then when you came home such a stud she couldn't wait to get her hands on you. Gwen loves you, Tony. It may have been bad timing with your father and everything, but trust me she wanted what happened. She wanted you so much, actually, I'm surprised she wasn't jealous about what went on between us." Diana squeezed my hand and gave me a seductive smile.

"I wondered. Did she knoweverything that went on between us?"

"Maybe not everything, but enough. It was all part of her master plan to seduce you anyway."

"I see, divide and conquer. You guys definitely had me in the palm of your hands last summer." It was actually nice to think about those events of last summer and recall the good parts.

"Enough serious talk. When that band comes on you'd better ask me to dance, Tony DiAngelo."

And that's just what I did. The band came on around nine and after they were warmed up and another couple or two were on the dance floor I took Diana's hand and led her out there too. They were a typical cover band, so it wasn't the type of club music, which I'd seen her dance to so memorably before. Still, though the dancing was tame she knew how to move and the way she was rubbing against me was putting thoughts in my head.

While we danced Diana slipped a hand between us and gave my erection a squeeze, which prompted her to nibble my ear and whisper, "Mmm, I hope you know how much I missed this."

I turned her face to mine and kissed her full on. "I doubt as much as I've missed you."

We both wanted to get out of the café, so after a couple more drinks I paid the check and we hit the road, but we couldn't figure out where to go. I didn't want to sneak Diana into my house like some kind of teenager and I knew going back to her place was out of the question. Of course I had the money for a hotel, but somehow that seemed kind of sleazy. Diana was the one who came up with a solution.

"So, Mr. Big Time, why don't you show me your fancy office," she purred, stroking me through my pants as I drove the Jag. It was a warm evening and I had the top down and Diana looked amazing with the wind blowing through her long blonde hair. Sudden visions of her bent over my desk made my cock throb.

Diana started unbuckling my belt and I asked, "Hey, what are you doing?"

"Don't you worry about it, just keep your eyes on the road. You're not going to want to make any sudden turns or stops for the next few minutes."

I couldn't believe it. With the top down anyone in an SUV or pickup was going to be able to see what she was up to, but knowing Diana that might have been part of the thrill for her. Once she had my rock solid eight inches free, she took me right in her mouth and started doing that zigzag thing with her tongue that makes my toes curl. Let me just say that it was pretty difficult to drive a stick shift while Diana was working her magic. Luckily we only encountered two other vehicles on the road high enough to see into the Jag before we reached my office. There was a soccer mom type driving a minivan who looked down at the blonde head bobbing in my lap with revulsion and a guy with his wife in an SUV. They both seemed to enjoy the show before speeding off into the night, hopefully inspired to have some fun of their own. The tight suction of Diana's mouth felt awesome, but I wasn't finished before we pulled into my parking lot.

"Mmm, that was a nice appetizer," Diana said, licking her lips as she sat up.

"Have I ever told you how bad you are?"

"Just about every time you see me. I think it's why you keep coming back for more."

I keyed the disarm code into the alarm and led Diana up to my office on the second floor. It still felt weird just sitting behind my father's desk sometimes and I'd never imagined doing anything kinky in there. You could tell my mother had been responsible for decorating the office because the walls and carpet were a light color and there was an elegance to the design. A soft leather couch took one wall, while a huge wall unit, with a media center and bookshelves, dominated the other. There was also a small conference table in one corner and of course the huge desk, which my father ran his empire from. When I finished closing the double door I turned around and found Diana perched on the front edge of the desk.

"You really are moving up in the world. I'm impressed."

"Don't let the surroundings fool you. I still barely know what I'm doing." I nudged between her legs and put my hands on her hips.

"I find that hard to believe. I've always thought you knew what you were doing." Diana loosened my tie and unbuttoned my shirt.

"I'm not sure those skills are going to help me here."

Diana grabbed my tie and pulled me to her lips. I moved my hands to her ass and pulled her into me, pushing my bulge between her legs. I felt her tongue probing and parted my lips to duel her tongue with my own. She was grinding herself back against me while running her fingers through my hair and I tugged her head back by the hair so I could bite her neck. God, I was so horny after so many months that I felt I could consume her whole. With frantic, fumbling fingers I worked on the stubborn latches keeping her top closed while Diana cradled my head at her throat. I threw her blouse on the floor and kissed my way across her chest, just above the line of lace that bordered the top of her stretchy camisole. Meanwhile, Diana was working on the buttons of my shirt, but grew frustrated and with a yank tore the remaining buttons out of the cloth, scattering them to the carpet.

Grabbing both spaghetti straps, I pulled the camisole down past her breasts and cupped both heavy orbs in my hands. I caught her nipples between thumb and forefinger and rolled them, bringing a tiny yelp from Diana's lips. She liked things on the rough side, so I wasn't gentle as I mashed her breasts in my hands. I leaned her backwards so she was practically lying on my desk and she flung my nameplate and pen set out of the way before she was impaled on them. Diana held my head tightly, guiding my lips to first one breast and then the other, directing my hungry mouth to where she most wanted attention. As I attacked her breasts with my tongue and teeth her cries grew louder in my darkened office. She gave up reaching for my bulge as she had to lean back on her elbows to keep her balance. Papers and files were being scattered all over my desk and I knew I was going to have quite a job in the morning getting everything back in order. However, sex with Diana was more than worth the sacrifice. She kept one hand on my head, but with the other she unsnapped her pants and tried pulling them down, eager to get me to where I could do the most good.

While Diana lifted her ass off the edge of the desk I yanked her pants and thong down, pulling her strappy heels off with them. She had a nice thin landing strip of dark hair between her legs, which revealed that her blonde was out of a bottle. I dropped to my knees on the carpet and used her hips like handles to pull her pussy toward my face while she thoughtfully spread herself open for me. Diana was already quite damp before I even kissed her down there and I deeply inhaled her scent. I brushed my lips against hers and allowed my tongue to peek out slightly and she bucked her hips off the desk in frustration at my teasing. "Tony," she whimpered, urging me forward with a hand on the back of my head. I smiled and flicked my tongue over her randomly, so close to her aching, throbbing clit, but ignoring it. I let my tongue delve deep between her folds, almost using it like a minicock to fuck her and Diana was gasping and moaning. After a couple minutes of working her up that way I moved in for the kill, going after her clit full force with my tongue. Diana screamed and writhed on my desk. I think she may have had a small orgasm when I licked her clit, but I didn't pause to find out, sucking on the little fleshy button while I pushed two fingers into her dripping pussy. Not to brag, but just about every lover has told me how good I am with my mouth and I knew that I had Diana completely under my power while I licked her pussy. She came hard, thrashing around, and I knew as long as I kept her cumming like that I could probably do anything, to her, I wished. I made her cum again while licking her clit before I lifted my soaked face from between her legs.

Diana kissed me hard, undaunted by her juices, which were smeared all over my face. "Fuck me right now, Tony," she demanded.

"Okay, if you're sure," I joked.

I dropped my pants and pulled her legs apart with her ass still on the edge of my desk. I lined up perfectly with the height of the desk and I slid all eight inches into her steaming pussy easily, making a nice wet sound as I did. Diana locked her ankles behind my back and held me there while squeezing her pussy around my shaft, trying to melt it inside her. Damn, she felt good and I was suddenly worried I might cum too fast after going so many months without. I held her waist and tried moving and her lock loosened up. I drove into her hard and fast and felt my balls slapping into her taint.

"Fuck me, stud," Diana moaned. "Fuck, oh yeah, fuck me!" Her big breasts were jiggling violently as I thrust in and out of her, putting on a nice little show. Her head was back and her eyes were closed and her mouth hung open and she looked so deliciously dirty lying there. I pinned her clit with my thumb and rubbed it while I fucked her and Diana kicked into overdrive, screaming bloody murder while she seemed to cum endlessly. Feeling her pussy rippling around me was all I could take and with a loud whoop I shot my load inside her.

"Jesus, Diana, that was fucking hot," I told her as I wiped the sweat from my brow. I pulled my pants up and held them at my waist so I could fetch a bottle of water from the mini fridge under the entertainment center. I swallowed half the bottle and offered the rest to Diana who was still lying on my desk gathering her senses. Watching her curvy young body and her chest heaving caused my cock to start tingling anew and I could feel myself rising from the dead.

"I've got to tell you, Tony, you put most of those college boys to shame."

"Only most?"

Diana laughed sweetly. "I can't let your head get too big, can I?"

I perched on the edge of the desk beside Diana and ran a hand over her, first massaging her breasts and then rubbing her swollen, red pussy. When I touched her clit her whole body jerked.

"Are you trying to start trouble again?"

"Can you handle it? Can those college boys go more than once?"

"It'll be an effort, but I'll take it if you can."

I leaned down and kissed Diana, feeling her hand wrap around my wet shaft and slowly stroke it. We lay there for quite awhile, kissing and caressing each other like old lovers before Diana pushed me onto my back and straddled me. She sat up completely straight, impaled on my shaft and smiled down at me while working her muscles and holding her breasts.

"Mmm, that feels so nice, stud. I've got you trapped right where I want you. I feel like I'm on top of the world."

Staring up at her she looked absolutely beautiful. "You look like you're riding high."

"I haven't even started riding yet."

Diana leaned down and kissed me and I felt her hips start to churn. Her hair hung in my face as she held herself up with her hands and pumped those hips. Her breasts hung against my chest and I felt them shake while she moved. She pushed up until she was hunched forward with her hands on my chest and her head hung forward. Now she could put more of her body into her motion and I felt her riding me hard. It sounded like she was saying "Fuck" over and over again, but it was mostly lusty, animal moans that escaped her lips.

Arching her back, Diana leaned all the way back and grasped the edge of the desk behind her. She was thrusting her hips forward and I had a great view of her whole body as she rode my cock. I thoughtfully put my hands on her hips and helped by pulling her down on my shaft, impaling her pussy even harder. Damn, Diana fucked like she studied porno movies or something. Not that I was complaining, she was incredible and I told her so.

"That's so fucking awesome," I moaned. I knew I could last longer the second time, but with Diana doing gymnastics on the end of my prick it wasn't going to be that long. I strummed her clit with my thumb and she screamed that she was cumming. As her juices flowed around my shaft I shot a second load inside her. Diana didn't stop riding until she'd milked every last drop out of me and then she climbed off the desk and flopped down on the couch.

"God," she sighed. "I'm worn out for tonight."

"That was some workout, Diana."

"I think you're going to have to carry me home, stud."

"Sure, as long as you explain to your parents why."

Once we dressed I drove Diana home and while she said she would be in Mexico for Spring Break, she promised to call me next time she was home. I drove home with the top down and the air blasting through the Jag felt exhilarating. For the first time in months I really felt alive, not that I was just making time in a suit. One thing was for sure, I definitely needed to get laid more often.

I tried to be silent as possible when I ventured up to my bedroom, but I needn't have worried, as my mother wasn't asleep.

"Tony is that you?" Mom called from her bedroom.

"Yeah, I'm just getting in." I ran a hand through my hair and straightened up my clothes, hoping I didn't look like I'd just been fucking my sister's best friend. I could see light coming from under the bedroom door and I eased it open far enough to put my head into the room.

"Did you have dinner plans, honey?" The bedside lamp was on and she had a book facedown on her lap. She sheet was pulled up to her waist, but even in the soft light of the lamp I could see the outline of Mom's nipples through her thin silk nightgown. She didn't parade herself around the house, but Mom did like nice nightgowns and it never occurred to her to cover up when I was around, but then why should she? She couldn't know what a perv her son is. I made very sure I looked her in the eyes as we talked, although I had the benefit of being in shadow.

"I had dinner with Diana Lansdale, actually. I ran into her the other night and we decide to catch up while she was home."

"That's nice. Is everything going okay at school?"

"Yeah, she just needed a little break. You know how dramatic teenage girls can be."

Mom laughed. "You should have seen me at nineteen. You'd have had no clue I could become the woman I am now."