A Night To Remember
“Okay, Shannon, what’s the matter?” I asked as we sat on my deck, the Saturday of the Memorial Day weekend. The rest of my family was out.
“Why does something have to be the matter?”
“You came over here to visit and you’ve barely said ten words since you got here. What gives?”
She didn’t answer right away, instead staring off into the distance. After several moments passed, she turned to me and said, “I envy you, you know.”
“Huh? Explain that one.”
“You know what I mean; you’ve channeled your…whatever you want to call it —frustration, maybe—into your writing, which I must say you’re very good at. You have the guts to pay a gigolo for sex. I’m too chicken for that.” She sighed. “Anyway, I woke up this morning feeling lost and actually thinking about divorce.’
“Please let me wrap my brain around that one,” I said. “I’ve always thought of you and Bill as the perfect couple. What’s wrong?”
Another sigh, “Nothing. Everything. Shit, I can’t even do a decent job of explaining.”
“Let’s refill our wine glasses and start over, shall we?” I said; which is what we did. Once settled back into our chairs, I asked, “Is this about sex or money? My experience says it’s usually one or the other.”
“Maybe it’s sex, but that’s too easy an answer, like a cop-out, I guess.” One more sigh, deeper this time. “It’s not as if I don’t love Bill anymore, yet there’s too much of a ‘been there, done that’ element to our love life, kind of like going through the motions. He’s, I dunno, wrapped up in his toys and his golf, and I’m into my work and my charity stuff, and I sit around thinking is that all there is?”
I began singing the old Peggy Lee song’s refrain:
IS THAT ALL THERE IS, IS THAT ALL THERE IS,
IF THAT’S ALL THERE IS MY FRIEND, THEN LET’S KEEP DANCING;
LET’S BREAK OUT THE BOOZE AND HAVE A BALL…
Shannon joined in, at least making the rendition somewhat musical. We ended with both of us laughing hysterically, which is always a good thing. When our laughter petered out, she said, “Yeah, so let’s keep dancing.”
“You and I’ve had some nice horizontal dances over the last few years, haven’t we? We’ve sung some nice melodies, too.”
I knew I was blushing. “Yes we have. Is that what this is about?”
“Not fully. I just keep thinking about what else is out there. How do I kick some life back into this body? YOU know how, that’s a fact. So maybe I equate you, Donna, with what I’m missing.”
“We’ve come full circle, so…what can I do? Take you into the bedroom and fuck you? Give you Derek’s number, so HE can fuck you? Or, maybe ghost write a story about you so you can be fucked virtually?”
“Oh, don’t be like that.”
“That’s a good start; anger is far better than resignation. Besides, it puts color in your cheeks.”
“What if I told you the answer to your question is all three?”
“I’d tell you to slow down, and we’ll do one at a time,” I said. Looking at her reaffirmed she was the most beautiful woman I knew. I wanted to run my fingers through her beautiful long blond hair. I wanted to feel her fantastic breasts rub against mine, nipples hardening all the while. I wanted to lose myself in her kiss. Except for when I was a girl, she’s the only woman I’ve ever slept with, and that’s coming from someone who’s as heterosexual as they come.
She said, “I love you, Donna; maybe more than anyone. And maybe that’s one of my problems, why I envy you so much.”
We sat there, heads tilted toward each other, not saying anything for several minutes, until I said, “I love you too,” and reached out to take her hand in mine.
“When are you expecting everyone home?”
“We have time,” I answered.
I didn’t plan this, but it was going to happen. We walked hand-in-hand to my bedroom where we undressed in silence. I smelled her musk. She’d been thinking of this, even if I hadn’t. We spent a long time touching, caressing each other’s breasts until they tingled (at least mine did.) My finger touched her and came away soaked. Our kiss was nearly endless, infinite, eternal. We slipped into a sixty-nine position, and our tongues went to work. I licked and sucked her and within seconds her first orgasmic tsunami hit the shoreline.
“Ohhhhhhhhhhhhh, Godddddddddddddddddddddd!” she cried out.
Mine took a little longer to arrive, and I wasn’t nearly as vocal as Shannon.
I gave her the gift of two more exquisite orgasms before we dragged our sweaty bodies into the shower. As I washed her hair, I said, “Does that take care of things for you?”
“Mmmmmmm, for a while, along with this,” she said, slithering closer under the shower’s hot spray.
We dressed and returned to the patio before my husband got home. I really don’t know if he’s ever suspected that Shannon and I have occasionally been more than best friends, and frankly I don’t know how he’d react if he did. He makes no secret of the fact that he’s lusted after Shannon for as long as we’ve known her, open with me about the draw of her beauty and her magnetic personality. Perhaps he’d be jealous I had her and he didn’t.
True to his nature, hubby fawned over Shannon before asking me when dinner would be ready. I love him, but damn his priorities.
Before she left, I asked Shannon if I could do anything more. She said, “You’ve done so much for my psyche already today.” She looked around to see if anyone was watching, then kissed me. “Why don’t you give me that Derek-fellow’s number? Maybe that’s what I need…besides you, my dearest friend.”
“I’ll have to check with him. You’re supposed to call his service first, though I have his cell number since I’ve seen him a few times.”
“Is he that good?” She must have seen it written on my face, saying “I guess he is. I better do this before I chicken out.”
A few days later, I called Derek directly. He was a little cool toward me, seeing how our last session ended with a discussion about a possible unhealthy fixation on my part. When I explained about Shannon, he whistled and said she sounded like a “firecracker ready to explode. I like that,” he said. “You were just like that the first time, remember?”
“How could I forget?”
“Is she as beautiful as you are?”
“Much more so,” I answered.
He chuckled, “I rather doubt that, but I know that my favorite client needs a little maintenance work done on her self-esteem every once in a while.”
“Oh, so I’m still your favorite client? I thought that had changed.”
“I’ve had second thoughts about our last…shall we say, disagreement, Donna.” He paused, and then said, “Actually, I was sort of hoping you’d call.”
“So, maybe you’re the one getting obsessed. Or maybe it’s just the recession killing your revenues.”
“Wow, getting feisty, are we? Okay, I’ll see your lady friend—Shannon is it? You’d better have her call my service number anyway to make the appointment. What about you?”
“You mean separate, or with Shannon?”
“Whoa, I meant separate, but suggesting a threesome had to come from somewhere within you. Have you two…er…”
“The magic number three has appeal, and the answer to your question is yes, we have.”
“Knowing you, I think that’s great. And still best friends, huh?”
“I have no problem with a two-for-one special for you, Donna dear. Still, have Shannon make the appointment, okay?”
“Will do. My pussy awaits. And wait until you taste hers.”
“I bet. Ciao.”
God! A threesome with the two hottest beings I know! I called Shannon right away and gave her Derek’s web site address, where she could check out his reviews and get the telephone number. I was naughty and didn’t tell her that I would participate too. Let that part be the icing on the cake.
The weekend soon approached. Thursday, June 3rd, brought the North Shore a nasty rain and wind storm that toppled plenty of trees in our area, but luckily we were spared. Hubby complained about all the branches and twigs he’d have to clean up in our yard. The poor boy. I was going to have more fun than that.
Shannon booked the appointment. When she called me to tell me, she said, “He’s got a room at the Hyatt Regency in Cambridge. I told his contact that I wanted an overnight; is that a good idea? Is he that good?”
“Yes, he’s that good, and yes, it’s a good idea. How would you like company?”
“You mean…you…the three of us? Will he do that?”
“Of course. In fact I’ve already cleared it with Derek, and it won’t cost us more. Are you okay with having me along?”
“Oh Donna, you of all people know the answer to that question.”
We planned our excuses to our husbands for the all-nighter. A vague girls’-night-on-the-town getaway was sufficient. “We won’t even tell them anything about where we’re staying—a true getaway—and if they need to contact us it’d be by cell phone, and only in a dire emergency, right?” she said.
“Sounds like a plan.”
She never flinched or even commented on Derek’s overnight four figure fee. She must have liked what she saw on his web page, going along with how I’ve raved about him in the past.
Late on Saturday afternoon, we stepped out in our best party dresses and high heels, ready to party. I pondered for a moment the expected thunderstorms but pushed that thought out of my mind. Nothing terrible would happen here. Shannon looked exquisite in her slinky black dress (as always.) She drove toward Boston as we talked about our upcoming adventure. She pressed me for details, and I tactfully refrained from telling her anything specific about Derek. She’d find out for herself tonight.
“I bought a new bra and panties at Victoria’s Secret,” she confessed. “They’re red and soooooo sexy.”
“I’m wearing the slinkiest thong I own,” I told her. “Anything else with my ass and I’d NEVER wear this dress.”
“What are you talking about? Your ass is divine.”
“Well, thank you sweet lady. I just wish my mirror reflected that ass-essment.” That got us both laughing uncontrollably.
As we neared the metro area, I called Derek. He told me he was checked in and “everything’s ready.”
When he told me his room number, I asked him about dinner. Shannon and I had discussed that possibility, letting her meet him and talk with him before the sex part. I was worried she would develop cold feet when it sunk in what she was doing. I knew, like me, she’d never cheated on her husband with another man, and we’d talked about that at length after she’d confirmed with Derek.
“Technically, you have cheated, Donna; with me, with Derek, and with the other gigolo dudes. So I guess it’s a little like rationalization.”
“Yes, Sigmund. I guess it’s like that. I’ve convinced myself that unless it was something more than simply sex with another man, it wasn’t cheating.”
“What if Bill found out?”
“Did Bill ever suspect you and me?”
“Not that I know of.”
“Well, there you go,” I said. “Bill’s had at least one affair that you know of, and I’ve suspected my husband of the same, so what’s the issue? Tonight is for letting go and having fun. Derek is a handsome and charming dream-come-true. Just wait ‘til you see him in the buff. He’ll charm you right out of those Victoria’s Secret undies before you know what hit you.”
“And you’ll then write all about it in one of your stories.”
“Probably. You’ve been okay with it so far.”
“I suppose if you do your usual stellar job of writing, it’ll be like having a keepsake to remember this night by.”
“You have my solemn vow, beautiful and sexy woman you.”
We were on Memorial Drive when she said with a sigh, “Sometimes I’m not sure about that ‘sexy’ part.”
“Well, I don’t know what’s wrong with your mirror, but whatever, you’ll be feeling mighty sexy by the time my buddy Derek is done with you.”
“These high expectations you’re setting may be difficult to meet.”
“Don’t worry about all that; just relax and enjoy the company. Everything else will simply happen.”
After parking, we went to the hotel’s restaurant. Derek was waiting for us. I still marvel at his beauty and his body every time I see him. He was wearing black dress slacks and a pastel lilac shirt that looked silk. Everything form fitting, the short sleeved shirt allowing full appreciation of his biceps. All that and his 1000-watt smile were enough to wet my thong panties.
Shannon leaned in and whispered, “Is that him?”
I nodded, and figured her panties were getting wet too.
Introductions ensued before we got a table. I was glad but certainly not surprised that Shannon got all his attention. She was the reason for tonight’s adventure, and I was sure he appreciated her good looks.
From her body language, I shouldn’t have wondered about her getting cold feet. While we ate and chatted, she hung on every word, leaning so close to Derek she could have fallen over, and that was before her second martini. I knew her well; the drinks weren’t liquid courage, but simply lubrication.
As Shannon paid the check, Derek winked at me and mimed a kiss. God, was this going to be a great night! We went up to his room. Once inside, Shannon grew a bit nervous. I knew the feeling: what’s the script, what’s next? She looked around the room, her eyes settling on the king bed.
She turned and whispered to me, “I’ll slip into the bathroom to get undressed.”
Derek heard her, so he walked up close to Shannon and said, as he put his arms out, “Shannon, darling, not so fast. Think of this just like dates you went on as a teenager. Let’s get to know each other, relax, get comfortable, and then do whatever feels natural. Okay?” He held her in something less than a lover’s embrace, letting her decide the level of intimacy.
Shannon looked up into his eyes and said, “You’re very nice. Donna was right. I do like you, and you are very handsome. May I kiss you?”
“You can do anything you like with me. After all, I AM yours for the night.”
Watching them kiss was a complete turn-on. Deep French kissing all the way, “swapping spit” as the old saying went, making me instantly jealous. I wanted to be kissed like that; shit, by either one of them! Shannon really melted into his arms.
“I’m going to get comfortable,” I announced to the kissing couple. I went into the bathroom and slipped out of my dress and bra. In only the thong, I freshened up my lipstick and my hair, then went back out to see how far they’d gotten. They were sitting on the edge of the bed, still kissing. Derek’s hand was under the hem of her dress, well up her thigh. She was purring like a kitten even as they kissed.
When they came up for air, Shannon said, “Whew, you’re quite good at this aren’t you?”
Derek smiled and said, “I’m good at quite a few things.”
I sat in the chair that was by the bed, and said, “He’s good at a LOT of things.”
Derek stood and pulled Shannon to her feet. “Allow me,” he said, and pulled her dress up over her head and off. Then he began unbuttoning his shirt, but Shannon wouldn’t let him finish, instead taking over the task. Her hands caressed his now naked chest, feeling his taut pecs and abs, and then moving on to his biceps.
He undid her red bra as she began unzipping his pants. Her bra was very pretty; too bad it had to come off. When she dropped his briefs, she gasped. No matter how many times I described his anatomy, she was still surprised by the sight of it. His cock sprang up as I knew it would; it was well trained. Like watching a really good porn film for the umpteenth time, I knew what would happen yet it aroused me anyway.
Derek snuck a look (and a smile) at me while Shannon adored his magnificent rod. It wasn’t as if she sucked him; it was more lick, kiss and caress. Like I said: adoration. I wondered if that’s how I looked the first time.
He gently lifted her off her knees and said, “How about we lie down?”
It was Shannon’s turn to look my way. I loved it—her expression was as if she’d just remembered I was there. I mouthed the words, “Go…fuck…go” to her.
Watching them was like déjà vu. I was reminded of the first time with Derek and how special it was for me, a forty-something married lady, to be utterly taken over and over again by a virile young man. I watched two fine bodies entwine in the dance of love as old as humankind. Because I’ve been intimate with Shannon, I knew how her body responded sexually, yet seeing Derek make love to her opened my eyes to the sexual splendor of my best friend. Derek knew how to do it, opening her up like a flower in bloom, both physically and metaphorically. He entered her missionary, with her legs wrapped around his tight ass. His opening rhythm was slow and sinuous, utilizing his exceptional length to full advantage. I began to masturbate.
She was moaning and crying, “Oh, this is good…so good…oh…oh…so good…”
He whispered, “Am I doing okay?”
As if he wasn’t.
She groaned, “Faster…I…need…faster…”
He did, pounding his magnificent length and girth deep into her vagina, soliciting ever louder affirmations of pleasure. Before Shannon could cum—and I knew she was getting close—Derek raised himself off her, and on his knees he held her ass off the bed and began fucking her that way. Her back arched and she sang the song of orgasmic bliss.
Derek looked over at me, since at about the same time I came too, though not as loudly as Shannon.
The déjà vu feeling continued when she asked him if he’d cum. I remembered his answer to me back then, and he just about said the same to her: “No. You’re not done with me yet, are you?”
In her post-orgasmic fog, Shannon was still nearly breathlessly, looking at Derek as if she’d hit the jackpot at slots. I knew that feeling. He motioned for me to join them on the bed. He kissed me in that deep way that radiates straight into your soul.
“You don’t mind watching your friend?” He said, once our lips parted.
“No. You saw me over there. Quite the turn-on, really.”
He turned back to Shannon, and it was her turn for one of his patented soul-penetrating kisses. She actually moaned as they kissed; I heard her! I went for that beautiful cock and slid him between my lips. He stiffened almost immediately. It was my turn to moan.
Shannon said to him, “Can you…go again.”
Derek looked down at me fellating him, and said, “Yes, of course.”
Shannon pulled him away from me and to her. He gave me a wry smile, as if to say ‘what can I do, she’s got me again.’ I didn’t know if I looked disappointed or what, for he then said, “How about a little porn film reenactment? You’ve both seen those movies, I’m sure, where two gals line up side by side and the man doggies them, moving from one to the other then back again. Both of you have such great asses to get behind, and poor Donna’s been neglected so far.”
“Great ass my foot,” I scoffed.
“Your feet are as great as your ass, my dear,” he said, proceeding to grab a foot and suck on my toes, which got me laughing hysterically.
We lined up on hands and knees as he choreographed. As he slid into Shannon, she whispered to me, “Oh Donna, thank you so much for setting this up. It’s exactly what I needed.”
I leaned toward her and we kissed, as Derek began thrusting in earnest. Shannon’s moans grew louder until he pulled out of her and slid over and into me. Now it was my turn to moan. The man’s stamina was truly amazing, moving from one to the other and back again just as he’d promised. Shannon was the first to orgasm, trilling “Oh, oh, oh, I’m cumming, I’m cumming!” before screeching in glorious paroxysms.
I wanted to see him, so I spun around, popping him out of me. I flopped onto my back, spread my legs and pulled him atop me. “Hard, do me hard!” I implored.
His thrusting was manic and soon I was screaming in climax. He said in a guttural voice, “Shit, I’m gonna cum,” and I felt his convulsions as he unloaded deep inside me. I’d feel bad for Shannon not getting any if I didn’t know he could recuperate fairly quickly.
Three spent bodies lay entwined on the hotel bed. Shannon cuddled up to him and was absently playing with his flaccid yet still wonderful cock. “This is so good!” she said. “No matter all the great things Donna’s said about you, I admit I had my doubts…until tonight, that is. I guess I didn’t want to believe how much I really needed this.”
“I take that as a compliment, beautiful lady,” Derek said. “My mission is to make sure I give you exactly what you need.” He chuckled, looking down to see how intently Shannon was rubbing his cock, trying to get him up again. “And I do believe you need some more.”
She moaned, “Oh Yesssssssssss,” and was showering him with kisses.
I leaned closer and whispered in his ear as Shannon moved her lips south. “You’re the best, but you know that already. Do her slow this time. She’ll want to hurry it along but you know what to do.” It was my turn to kiss him, slipping my tongue between his moist lips, at the same time Shannon slipped a part of his anatomy between hers.
Derek took his “mission” into the missionary position and with her legs wrapped around him, began the tantalizingly slow fucking rhythm. As before, though now much closer to them, I watched in voyeuristic amazement at the sight of his tight, muscled ass cheeks clench and relax on each thrust into my friend. His focus was resolute: Shannon and only Shannon. Her back arched as she tried to urge him faster, as I’d predicted, but Derek kept at the steady pace that might prolong her orgasm—or maybe set off the many multiples I knew she was capable of. Nevertheless, she would be delivered to the same blissful land Derek’s skill had taken me before.
Derek had a way of ‘corkscrewing’ into you as he thrusted—it must have taken lots of practice—so he hit spots a woman perhaps didn’t feel normally. Of course, his length and girth did some fantastic things too. He was doing all those things to Shannon now, and she was responding very vocally.
Shannon was getting the deluxe-Derek, multi-orgasmic treatment. She was crying and wailing so much it was hard to separate her orgasms from one another. As she screamed, I kept my gaze on Derek’s face to see the same, Zen-like countenance as he fucked her with metronome-paced precision.
Until then a detached, though not unemotional observer, I slid closer and began stroking his rippling ass muscles. When my hand slid down to cup his balls, he moaned, “Don’t.” He tensed and then ejaculated, with a low throaty groan. I felt him expel every rope of cum, and Shannon evidently did too, for she howled as one more orgasmic wave swept through, her juices mixed with his. I knew from experience just how filled she was.
Shannon sighed and said, “Again…and again, and again, and again…”
Derek kissed her gently on the lips, and then said, “Sssssh, we have all night, hungry lady.” He turned to me and gave me a playful slap on the ass. “Why did you do that? I swear she had at least two more big ones in her.”
I chuckled, “Couldn’t help myself. You know why mountain climbers climb the mountain—because it’s there. Well, your ass is so magnificent I had to touch it, and then…”
He laughed too. “Yeah, I know.” His expression changed as he looked at me. When he rolled over to be facing me straight on, he said, “You’re quite the enigma, beautiful Donna. You want no-baggage sex yet you keep coming back for more, even setting this up with your friend here. I know you’re looking for something; I don’t know what yet.”
“Just calling me beautiful makes me want to cry,” I said, indeed tearing up. “You’re the best lay I’ve ever had, and yet it’s not all, and you know it.” I didn’t say it aloud, but I mouthed, “I love you.”
He groaned ”Oh Donna, you can’t,” but our lips came together and I was in heaven. I had no perverted fantasy. I didn’t believe he’d run away with me like Hollywood would have it. I wanted to feel like a desirable woman as he made me feel, ignoring the wrinkles and the extra pounds beyond his commitment to service. This kiss was the embodiment of my fantasy, and I reveled in it.
When we breathlessly stopped kissing, I whispered, “Please, make Shannon feel like I do. You know what I mean.”
I climbed out of bed as he turned back to Shannon. His stamina was amazing; almost superhuman. Shannon was exquisitely sex-drunk, and by the looks of Derek’s swelling manhood, she would soon be drunker still. Yes, ‘drunk’ was an apt analogy as was ‘drugged.’ She was now addicted to Derek’s charms. She pulled him into her, bucking and mewling, and finally wailing as one, two, three waves of orgasmic ecstasy washed over her, swamping her.
Momentarily sated, Shannon made a comment about being hungry again. I didn’t know what time it was or how long we’d been at it, but Derek assured her that room service was still available, so we ordered enough to feed an army. Considering what Shannon was paying, the cost was far from Derek’s service-with-a-smile mind.
Food washed down with champagne, then more sex; first me, then Shannon. Again.
The king bed accommodated the three of us in post-coital slumber, satisfied by food, drink and sex, Shannon on one side of Derek, me on the other. I slept peacefully, warm against the naked body of my favorite gigolo. I awakened to a bouncing bed and looked over to see Derek between Shannon’s splayed legs doing some hot horizontal dancing. I just watched. Here were the two hottest, most sexually charged people I’ve ever slept with, fucking like two horny teens on prom night. Her breasts heaved. His magnificent cock plunged. Their rapturous expressions priceless, I once again realized how this sort of thing was never simply a service to Derek; he was enjoying the sex as much as she was.
We showered and spread kisses all around. Once dressed, Shannon didn’t seem as if she could say goodbye. Instead, it was me who formed the words to thank Derek for a tremendous night. Shannon simply went for the deep French kiss one more time. I’d say that was thanks enough. I asked Derek if he would join us for breakfast but he declined.
“You both have sufficient alibis for this, don’t you?” he asked.
We both assured him we had it covered.
I finally got Shannon coaxed out of the hotel room and it wasn’t until we were well into our elevator ride that she hoarsely said, “Oh, Donna, thank you, thank you.”
I tried to lighten the moment by saying, “No big deal, after all it was your money that paid.”
She didn’t want light, just heat. “Can I ever be satisfied in bed after this?”
I took her hand in mine. “Sssssh, we’ll talk about it later, okay?”
We left the hotel and along the route north toward home, we stopped and ate breakfast. Shannon’s sexual appetite may have been satiated, but her physical one seemed to be in overdrive; I never saw her eat so much food.
On the rest of the drive, I pondered the metabolic connection between the two appetites. When I was red hot and at my horniest, I rarely thought about eating. So much for the ‘fueling the fire’ hypothesis.
Yes, we did talk at length both in the car and later. I didn’t try to assure her of anything regarding her own reaction to the sex with Derek. Instead, I reminded her of my roller-coaster emotions. “This past night put me back on that roller-coaster, you know. Shit, I told him I loved him, for God’s sake, and maybe I really do. He can’t possibly treat all his customers like he’s treated me—he can’t. So, you see how fucked up I am?”
She laughed, “So much for helping me cope!” Then more seriously, she said, “I may not have understood when we left the hotel but I think it’s coming to me. I’ve held in what I need for so long and only you know about it, and you knew what I needed. I love you, Donna sweetheart. I understand your dilemma. Derek is more than just a fuck-buddy, way more. So you—we—have to figure out how to reconcile the needs that Derek fulfilled and those of our marriages and lives.”
“Yeah, that’s it in a nutshell,” I said and chuckled.
The hand not on the steering wheel snaked across the center console and found mine. “Well, we’ll figure it out together, won’t we?”
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