tagGroup SexThe Designated Driver Chronicles Ch. 04

The Designated Driver Chronicles Ch. 04


Have you read the first three chapters of this story? Perhaps you should just so you get the gist of the setting - or not. If you are underage or at all squeamish with variations of sexual pleasure beyond the male/female Protestant ethic nuclear couple, why are you reading this? Go read something else! If you are reading this, enjoy it and give it a score. All feedback is welcome. A special big time thanks to "LarryInSeattle" for his astute editing of this chapter, too.


August kicked in like gangbusters. My business went crazy during the first weeks of the month. I was editing and revising my novel by day and driving rich drunks around at night. After my experience with Wayne (see Chapter 3), I decided to concentrate on working as much as I could and concentrating only on the front seat of the car. I worked and I found myself with five or six jobs a week averaging about three-fifty a night. I was making a ton of money and reading the classifieds in order to get a cool year-round rental house instead of the room I was renting in a private home. I had goals. I needed to finish my book and I needed to get my own place. This driving gig was my vehicle.

My jobs were for the typical Hedge Fund prick. Since it was the final month of the summer season, many had taken the one-month deal on a fancy house. Hell, a premium house rental for the month of August in the Hamptons starts at about one hundred fifty thou. No shit! I picked up at several different ocean-front estates and drove some mighty fancy cars. Most of the rides were the same - pick them up sober and polite, bring them home all sloshed and sloppy with similar characteristics; rudeness, nastiness, loudness and a high degree of horny, mostly of the soon-to-cum-by-masturbation variety. I watched my p's and q's and quietly collected the cash.

Not that some of the rich babes didn't get my juices flowing, they most certainly did but I kept it in check. I jerked off many times during the few weeks of a rather balmy month. I usually jerk off in the same way as I suppose most people do. You know what gets you off, right? Well, my routine rarely varied. After I returning to my room, thoughts of crotch shots and tit peeks had me rubbing my cock through my pants. I get naked and watch some porn clips on the web. Then I go to my erotic story sites and read stories, mostly of group sex and bisexual subgenres. I'll find a good story and stroke with more determination. I take a piece of paper towel and put it on the floor in front of my computer screen. Then I jerk away until I feel the seed rising. When my swollen and red helmet is ready to explode, I cup my palm under the head and shoot into my palm. When I've squeezed out my load, I sit back and lick my hand, cleaning all the tasty cum from between my fingers. Sometimes, this gets me hard again and I find another story. Me, I like to cum at least once a day. Me and my hand make good partners.

I'd just finished cleaning myself when I got an email from Gayle, a lonely wealthy married woman I'd driven (and made love to) earlier this summer (See Chapter 1). It read, “Hi Ray. How is your summer going? I know this is sort of last minute but could you pick me and Reenie up at her house on Wednesday night at seven? Gayle.”

I emailed her immediately telling her I would be there at six forty-five and that I was working by myself now and only accepted cash or PayPal. She wrote back that it was no problem and would see me then. Then, with my head dancing, I jerked off again.

Late Tuesday, I received a call from Reenie (See Chapter 2). She was all excited and talking quickly. I got how excited she was, about how she hoped for an adventure and other stuff I didn't understand. I had to break in.

"Reenie. What are you going on about? Gayle will be with us? You two are going crawling, right? Where to, red/bar...nobu?"

"No, it's not going to be like that, Ray. Look, let me explain...but this is between you and me, right? Don't let Gayle know that you know any of this, all right?"

"Okay, my lips are sealed...I hope around your clit again, Reenie."

"Oh, I think that is very doable, my pet...but there's more. Last week, Gayle and I got a little drunk during an afternoon around her pool and the beach. We talked about a lot of things but mostly about sex...a lot about sex with you. You received rave reviews, believe me."

"So you want me to do it again with both of you?"

"See that's the thing. She wants to go out bar-hopping and I want to have a threesome but she doesn't know that. See, last week, when we were drunk, she admitted to me that a masseuse had worked on her and introduced her to woman-to-woman sex. She quite enjoyed it. I want to do her, too...I always have. It's been a fantasy of mine for years and suddenly I see a way to make it happen. Are you in?"

I laughed. "Am I in? Don't worry, leave it to me. Ooh, this sounds like major fun."

She laughed, too. "Good! I'm wet thinking about it."

"Oh, I have a question for you. What kind of name is Reenie? It's a new one on me."

"No biggie. My name is Renée but since I was little they called me REE-nie, not re-NAY. Get it? My friends just call me "Ree."

"Well, alright. I think that now as we're intimate, I can call you "Ree."

"Works for me!"

Wednesday evening couldn't come fast enough. I picked them up at Ree's house in Water Mill and they both looked 'drop-dead'. Gayle was wearing a transparent cream-colored blouse with a matching cream-colored bra. You could just see a hint of dark nipple through the bra. And, as it was a warm evening, she wore brown shorts showing her lovely long bronze legs. She was very earth tones. Reenie was decked out like a wealthy slut. Her light blue shorts cupped her ass cheeks like a lingerie ad. With no visible panty line, you had to know that the smallest of thongs hid below. Her large tits literally popped up and spilled out her bra filling her low cut cleavage with fantasies of sticking my cock down there.
"You two look awesome. You both look good enough to eat."

"Well, I hope you're hungry!"

"So what do you have planned for two cougars tonight, Ray?"

"First, I think I'll take you down to red/bar so you can check out the merch. Have a couple of drinks and then report back. I'll take it from there. I have options."

"And what if we pick up some guys? What happens then?" Gayle was projecting.

"Then I take the four of you wherever you want to go. Just be careful who you pick up. A lot of these guys are creeps. Don't concern yourself with scoring. It's when you don't want to score that you invariably do. But if you don't, it would be my pleasure to pleasure the two of you."

"Yeah...sounds like fun to me." Ree piped in.

"So, let me ask you something? Have you satisfied your urges thus far this summer?"

"You mean, besides you? I happily admit that I've fingered myself several times thinking about our sex together. Good ones, too." That Reenie!

Gayle was quiet except to say that she'd been a bit wilder but that discretion was more her style. "I don't babble like my friend here."

"Like hell you don't. Just give her a couple of drinks!"

"Well then, here you go…red/bar." I pulled into the bar off Hampton Road, a scene-making modest little restaurant/bar/meat rack. "Two drinks and then report in."

I found myself rubbing my crotch through my pants while I waited for them - a little pocket pool. A good hour later, the two came out looking a little worse for wear.

"So what's the story?"

"No, not a good crowd," said Reenie, "too many guido bankers and seedily rich Russians. Gee, every guy seemed to be drooling. Not my scene, not for me."

"Me neither. None of these guys seemed to have style or personality or class or...I don't know, maybe I expect too much from THE Hamptons." Gayle seemed resigned. "You were right, Ray. When you're not on the make, you score. That's how it goes."

"So, where to? It's still Attitude Adjustment Hour."

"I really have to go to the Ladies Room. Could we stop at your place, Gayle? It's right around here somewhere, isn't it?" I smiled at Ree's sly attempt to move the party.

"Sure. Good idea. I have to go, too. Let's go and plan our next move there."

"Good. I could tap, too."

A few minutes later, I turned onto Gin Lane and slowly drove past the home of one of the Koch brothers, the home of Herbert Allen, a few other moguls and finally into her driveway.

Reenie ran right off to the john. I turned to Gayle, "So where's your kid?"

"Oh, my sweetie is with the nanny at Ree's house, with Ree's kids. Why, what do you have planned?"

"I thought maybe we'd have a drink or two...then maybe smoke this fat joint...then maybe skinny-dip in your pool...and then have a three-way. Waddayasay?"

"How do you know we'd like that? Maybe we don't want to share you."

Reenie joined us with an open bottle of wine and three glasses. She caught the last part of the conversation. "Maybe we don't have to share only him? Maybe we can all share each other. Come on, let's go out onto the deck." Once out there, she said to Gayle, "So tell Ray about the massage..."

"Sounds to me like you already spilled the beans, my friend the bitch."

Ree giggled, "No, I just teased him a little. Come on, share it with - especially with Ray. Tell him like you told me."

I sat back in my chair and sipped the wine. I pulled a thick joint from my pocket and lit it up.

"Okay, so I was having a bad day. I exercised a bit hard in the morning, then had an ugly session with my finicky horse and then I found myself in spin class and very sore. One of the other women suggested I check the bulletin board by the front desk and call one of the masseuses listed. And so, on my way out, I wrote down a few numbers to call. On the way home, I was lucky to catch the very first one, Amelia, who was more than willing to come to my house right then. A few minutes after I got out of the shower, she rang the front door bell. The housekeeper answered and sent her upstairs to my room.

“She surprised me as I was sitting at the vanity naked. I quickly covered myself in my robe but she was nonplussed. She was a very pretty young woman, with a small but strong body. She had a South American accent. She set up her massage table in the bedroom and asked me to disrobe and lie down on my front. She folded a small towel over my butt and I let her coat her hands and my skin in warm oil. I was putty in her hands and all my aches vanished under her capable hands. My horse had given me a bit of a hip-pointer and as she worked her palms from my side around and down my ass cheek, I sighed. I told her how good her hands felt. She kept telling me how beautiful I was. I was really blissed out. When I felt her hands rubbing and molding my ass checks, I sighed again and spread my legs a little wider. I loved how her thumbs began to run down the crack of my ass to just above my asshole. Several times, I pushed my ass back at her and she squeezed it. I was clearly turned on by her touch. I'd never experienced feelings like this before and I was just letting it flow. And I was flowing! The smell of my aroused pussy infused the bedroom."

With that remark, I stood up and started to strip down. They were watching me. "Go on with your story. It's turning me on and I think I want to take a dip...in the pool, I mean, first." I continued to strip down until my cock bounced against my gut. Then I moved to the pool and jumped in. I swam back to the corner of the pool and hung off the coping. "Go on. I'm all ears again."

"So she told me to turn over. I was very wet. My nipples were like hard little beans. She smiled and told me how beautiful I was, how beautiful and perfect my breasts were, what good shape I was in. Her hands worked my hands, my wrists, my joints. She flexed and cracked my ankles and toes. After each leg, she spread my legs a little further apart. I was lying there completely exposed to her. Her hands traveled up my legs to my thighs and nearly to my sex but just stopping. A few times, I felt her brush by my pussy and each time it electrified me. I was really juicing up now. I knew it was obvious but I didn't care. She moved up to my shoulders and head. I was a mound of jello, nearly catatonic. I swooned when I felt the warm oil dripping on my chest. I groaned when I felt her hands rub the oil into my breasts. Her technique was divine, the way she curled and caressed my nipples. I was disappointed when she got off the table. "Shall I continue, ma'am?"

“I groaned again. "Please don't stop. It's wonderful. My body feels so good."

"Wonderful. Let me get some more oil. Would you like to move onto the bed? I can put some sheets over it?"

“I groaned. The next thing I know, she was holding me and leading me onto the bed. I felt her skin against mine and I liked it. I lay on my back with my arms and legs spread. I felt her get up next to me and run the oil into my cleavage. She leaned over me and I had the most delightful sensation of her small breasts caressing mine and the oil sliding between us. She made me feel like an angel, I swear." I got out of the pool and strutted my stiff dick over to the bottle of wine.

"I like your style, Ray. I think it's time I joined you. Her story has me so damp..." Ree took very little off before she was also naked. Her little thing, no more than a wisp of butt floss, was the same blue as her shorts. Why would they be any other color? Her breasts were fabulous, big but young and firm. She ran her hand down to her pussy and rubbed it before lifting it to her nose. "Oh, jeez..." she moaned.

"So I take it that she made you cum and you loved it."

"Elementary, my dear Watson. That she did." Gayle was disrobing now. Her panties were also the same color as her bra and her creamy-brown outfit. How did I know that? Fancy and lacy, too. Probably Italian or French or very expensive. Still they made her legs and her mound stand out, especially after she removed them.

"Did you reciprocate?"

"No, I didn't get the chance but I wanted to. At one point, when she was sliding her chest over mine, I cupped her small breast in my hand and it was thrilling. She went down on me but when I tried to return the favor, she pushed me away. Her massage of my vagina sent me to the moon and I was wiped out for some time afterward." She jumped into the pool. "Who's joining me?"

We soon found ourselves splashing each other, playing touchy/feely and generally being silly. After a while of this and feeling a bit exhausted, I pulled both women to the side of the pool and sandwiched myself between them.

"I love all these breasts. They sure feel wonderful." I tweaked each nipple and caressed them. I took Ree's hand and placed it on Gayle's breast which caused Gayle to sigh. I then did the same with Gayle's hand and Ree's handful and a half of breast. Like ducks to water, they both enjoyed it.

"So here's my idea," I said as I held them closer. "Let's go inside and make each other feel good. We'll get some baby oil and start by massaging each other. Then we'll let it go where it wants to go. What do you say?"

Ree smiled wide and said, "Come on, let's do this. I want to do this so bad, Gee."

Gayle suddenly seemed nervous, "Do you think this is right? Could this ruin our friendship, Ree?"

I shook my head. "Gayle, stop overthinking. Go with your desires. If anything, this will probably make the two of you closer. Come on."
This quieted Gayle, probably because she really had no negative feelings about it in the first place. We got out of the pool and toweled off. Taking our drinks and the ashtray, we followed Gayle into the house and upstairs to her bedroom. Gayle stripped the bed and threw a sheet atop then got a bottle of baby oil.

"Okay, so Gayle, you lay down on your stomach first and Ree and I will do the honors of feeling you up." In a flash, she was stretched out. Her ass looked so fine and with her legs slightly spread apart, a little pink was turning us on. We each took a leg and began to rub oil from her feet to mid-thigh. I decided to let Ree explore as I moved to Gayle's head and began to work her shoulders.

"This feels so good. I feel so special."

"It feels good to touch you. Your skin is so soft, so different from what I know." Ree's palms were now working Gayle's butt, occasionally sliding into the crack. I saw that things were moving as planned and so I told Gayle that it was time to turn over. She did and immediately, Ree's hands were rubbing oil onto her. "Your body is so beautiful. You have such pretty breasts."

"I wish they were a bit bigger. I'd love to have tits like yours. God, are your tits great!"

"I have an idea." I took some baby oil and rubbed it onto both of their chests. Then I had Ree move up and over Gayle, lean over and let them slide their breasts together. Immediately, they cooed and I noticed their crotches come together. They rubbed and rocked together for several minutes. The scent of their oozing vaginas was unmistakable, quite delightful and maybe even call it heady. Ree leaned down and took a nipple between her lips. Both women began to moan as they seemed to relish the experience. I sat back against the headboard and idly stroked myself as I watched these two absorbed in their first-time sex.

"Can you smell each other? You are both very, very turned on and your scent is permeating the air. It smells divine. Is it good?"

They were both abandoning any resemblance of protocol as their bodies slid against each other and their hands traveled. "It feels great," Gayle moaned. "Ree, you're so soft." Her hands squeezed breasts and pulled and twisted nipples. Her lips quickly took over. It was amazing to watch. Ree slid her hand down to Gayle's mound and began to explore her folds occasionally lightly spanking it.

"I can't take the waiting. I have to know." Ree moved down between Gayle's legs and with her fingers she delicately pulled her lips apart, examining and touching her parts and probing the layers of her lips. She pulled the clitoal hood with her thumb then slowly let her head drop and took a long slurping lick. "Oh God, that tastes delicious." She buried her face in Gayle's shaved woofer and went wild.

"Slow down, Ree. Savor the experience." It was moving too fast for me. I suppose that for my own selfish reasons, I wanted it to last longer.

"Fuck that, Ree, just don't stop." Gayle reacted to the tonguing and pushed her pussy up. "Let me do it, too." Ree paused as Gayle swiveled around on the bed, placing her head directly under Ree's dripping snatch, her tonguing licking Ree's hole. "Oh, that does taste good...and the scent...oh." God bless pheromones.

My cock was about as stiff as it could become and I did not ignore it. Watching these two enjoy - no make that - wallow in their first woman to woman sex was revelatory. I'm certain that being the spectator as well as emcee to the event had a more erotic effect than being a participant. Nah! But as they became wilder and very deeply into it, I began to sweat. I wanted so much to touch and taste, too but at the same time, I could not stop watching. The scene was intense as they clawed and squeezed each other. Their moaning provided a powerful soundtrack. Obviously, they were enjoying themselves. My stroking sped up.

Both women were now humping the others face. Ree could not contain her previous pent-up curiosity to feel, touch and love another woman. "Oh, baby, that's it. You're making me cum. I'm gonna..." Her body began to convulse, her legs thrashed and her nipples looked about to lift off to the moon.

"Yeah, cum. I want you to cum for me. Let me make you cum." Gayle's lips were locked around Ree's clitoris as her tongue whipped around it. Both pussies were now audibly squishing as they slurped and bounced off each other. Gayle's face was soaking as Ree's juices flowed over it matting her hair. Ree let loose a cry somewhere between a warble, a whine and a grunt. Her legs went rigid as her orgasm erupted and her hips made waves as she came and came. Finally, she calmed down and rolled over onto her back.

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