Can Dolly Seduce Her Clients Son
"Dolly, I think my sonmay be gay." That’s not a line I hear very much from my clients. In fact, it was a first. Phillip, the gentleman who made the statement was a steady client, a good man, and I could tell it was an admission he didn’t care to make. The comment came as we relaxed in my hotel suite after a torrid session of mind-blowing sex. His son, 24, “dropped the bomb” on him just a few days before. And like any red-blooded, high-testosterone hetero American male, it hit him like a mortar shell.
“How does he know,” I asked? “Has he had sex with other men?”
“That’s the weird part,” he told me. “I don’t think so. He just said, Dad, there’s something you need to know and you’re not going to like it. I’m gay. I have no feelings for women at all, only men. And I have a boyfriend now that I’m thinking of sleeping with.”
You have to understand that in my line of work, the sensual experience is often only part of the package. Men tell me things they’d only tell a therapist, as if I know the answers. The last time I looked, I did not see a diploma on my wall for a masters or PhD in psychology, but I have indeed been to the school of “street smart psychology.” And I have to admit I know it helps just to have someone willing to listen. Phillip’s wife was a control freak. In bed with her, he could never be in control. Which is why he frequently came to me.
“Has your son ever dated a woman … I mean, slept with one?”
“Once … he told me about it this week. It was when he was in college.”
“He said he just could not get aroused. No interest. No erection. No excitement. Purely platonic. She apparently was very pretty, a total sweetheart. She was definitely ready. But he was not and they broke up. She was very disappointed. He was very embarrassed and questioned his sexuality.”
I felt like making light of it, saying something like “Well, one limp cock does not a gay man make.” But then I realized this was no time for levity. I could see Phillip’s pain and disappointment, which of course I expected. What I did NOT expect was his next proposal.
“Look, this may sound bizarre. But I have an idea. In my mind, there may be a litmus test to determine if he really is gay. And frankly, you might be it.”
I could see where this was going.
“How about if I hire you as a consultant, per se, to seduce my son. I mean, we’d have to really figure it out because I wouldn’t want him to know I was involved. If he can’t get it up with you, then I’ll know he really is gay. But I think his main issue is that he just doesn’t have any confidence with women. And if you could give him that confidence ….the whole “gay” thing just may be history.
I was flattered, of course, but told him I’d have to think it over. It’s one thing to provide R&R for stressed-out male professionals. It’s a whole different ball game to be asked to perform a “gay or no-gay” exam.
Phillip showed me a picture of his son, Gary, on his phone. Shit. He was cute … REALLY cute. There was a part of me that wanted to say, “No, I really can’t do this.” But seeing that picture of him, there was another part that said, “Fuck yes!”
Then Phillip handed me an envelope. It was sealed with a handwritten note on the front, “To Dolly … to be opened only upon proving my son isn’t gay!”
Now THIS was different. Payment in advance but only if I succeeded performing what might be an impossible task. I was quite confident of my sexual prowess, but to be able to turn a possible gay man straight? Phew … I had to think this over.
When Phillip left that night, I lay in bed looking at that envelope. It was thick and heavy. Dare I open it beforehand to see just how much this effort might be worth? No, I decided. I admit he had me hooked. He knew I was always up for a new experience. But how could I pull this off? How could I make meeting Gary seem “coincidental”? And what if he didn’t find women older than himself appealing?
So I slept on it. And the next morning, it hit me. Yes, I could do this. Over my morning coffee I came up with a game plan. “MISSION GAY OR NO-GAY” was underway. I couldn’t believe I’d agreed to do this, but suddenly the planning was becoming fun. My sense of risk and adventure had kicked in yet again.
Phillip had said Gary liked to hang out at a bar next to the hotel where I was staying that was actually pretty high-end. That was a good sign. He had good taste, and I would feel comfortable there. He apparently went there every Friday night after work, around 6 PM, with friends ….all male so I was told, but it was NOT a gay bar. Gary had an Ivy League degree in business and was working at an investment firm.
So Friday came and I put the plan into action. First …. a trip to my favorite lingerie store. They know me there quite well and I simply told the sales girl, “I need something to make a man cum without us even touching.” She grimed from ear to ear. “Wow! That’s a tall order. What are you thinking? Submissive? Dominatrix?” “Great question,” I thought. “Maybe you should give me one of each.” She laughed and headed for the racks. “I’ve got you covered … or uncovered maybe I should say.”
Thirty minutes later I walked out of that store with not one but two outfits, feeling so sexy I thought I MYSELF was going to cum from just looking at my image in the mirror. Damn, that girl knew her merchandise.
At five o’clock, the “pre-game-show” began. First a shower, makeup and hair (I left it long and blonde as 90% of gentlemen really do prefer blondes), and then the lingerie. It was a fifty-fifty shot … sub or dom. I decided to go sub, as it seemed like Gary would want to take control like his father. The outfit the clerk had chosen for me was perfect ….see-through lace everywhere … bra … panties … garter belt … the whole package. But very elegant and sophisticated at the same time. DAMN I looked hot in my bathroom mirror.
I must have tried on ten dresses to figure out a top layer and finally settled on a somewhat corporate but slutty look. Smoky grey thigh-high stockings, black stilettos, a white blouse with LOTS of buttons, which of course I left open enough to reveal just the right amount of cleavage, and a drop-dead black jacket that just begged guys to peel it off me to get to the buttons on that blouse. I normally reserved this outfit for corporate business meetings when I needed to “close a deal” (it never failed), but this was definitely going to be one of my most challenging “deals” ever.
Then … back to the mirror for a quick makeup touch-up. I normally shy away from brighter shades of red lipstick, but I had a special idea on this occasion and decided to go totally scarlet. Honestly, wearing this outfit sitting alone at a bar, my biggest concern was that someone would try to pick ME up before I hit my “target”. So I decided on a light raincoat coverup to keep everything under wraps … until the right moment came along.
I walked into the bar at 5:45 and very few people were there, definitely not Gary. So I ordered a dirty martini with double blue-cheese-stuffed olives (a favorite for this type of occasion … you’ll see why) and waited. My timing turned out to be perfect, because within five minutes in walked Gary with three other guys. WOW! He was even better looking than his picture. Great smile, great shape, and the guys he was with certainly did not give off any “gay” vibes. One of them was already chatting up a girl next to them. I removed my raincoat to reveal the first layer of what was to be “the show.” If there’s anything I ‘ve learned about guys who may be a bit “reluctant” to stiffen up, a very slow sensual seduction gets the Phoenix rising.
I pretended to not notice them at all across the bar and summoned the bartender. “Excuse me, but see that young man over there with the white shirt and gray jacket? I’d like to buy him a drink: just like mine, a dirty martini, double olives. But would you bring it to me before taking it to him?”
The bartender looked a bit puzzled but agreed. He brought the drink to me, and I very carefully placed my scarlet lips on the tip of the glass to add a very obvious bright red “kiss” on it. “Now, you can take it over to him,” I said. This was obviously something the bartender had never seen before, as his hands were shaking as he carried it to the other side of the bar.
I watched as he approached Gary, gave him the drink and gestured over to me. When Gary looked up, obviously surprised, I smiled, raised my glass as if for a toast, removed the two olives from their toothpick, and very seductively slid them past my tongue into my mouth. Get it? Two balls in the mouth?
Well … I must say … that move did have the right effect … at least on Gary’s friends. Gary just stared at me and blushed bright beet red but his friends, looking at me as well, howled and patted Gary on the back! YES! That to me was sign number one that there was hope for the success of this mission. His friends were obviously not gay. My biggest concern at this point was, “Good grief. Am I setting myself up for a five-some?”
I played it very coy, not even looking over at him for a few moments, when all of a sudden I felt a tap on my shoulder and turned to see one of Gary’s friends, obviously very sure of himself, with Gary standing very shyly right beside. “Miss, on behalf of my friend Gary here, I just wanted to say thank you and introduce you to him.”
“Hello, Gary, I’m Dolly, and I apologize if I disrupted your little party, but I’m in town for a few days on business, happened to see you walk in, and thought, THAT is a young man I’d like to know. Have a seat.”
Gary’s friend laughed, disappeared, and Gary very quietly and awkwardly sat on the barstool beside me. He had brought his martini with him but hadn’t touched it, so I proposed another toast. ”To dirty olives!”, I said. He reached for his glass and his hands were literally trembling. I saw an opportunity, removed the olives from his glass and asked, “Do you mind? I’m just wild about blue-cheese stuffed olives soaked in a good vodka.” He shook his head that he didn’t mind and I again seductively slid them into my mouth. But this time, I didn’t swallow them.
“Do you know why I love these stuffed olives so much,” I asked. “No … actually … no,” he said. “Because I can do this with them.” I then used my tongue to push the creamy cheese filling out of one of the olives so it dripped out of my mouth over my ruby red lips. “There’s just something about making something hard in my mouth explode with a creamy texture that I just find SO delicious.” I then swallowed the cream, and licked my lips clean. “Would you like to try it?” I asked.
Honestly, it was all I could do not to burst out laughing when I realized his friends were watching every move and literally ROARED from the other side of the bar. Gary looked like he was in a trance. “I … I … suppose it’s an acquired taste,” he said.
Wow, was that ever an opening line if I ever heard one.
“Would you like to acquire it?”, I asked. “Or, I’m sorry, would you help me acquire it on a higher level.”
“A higher level?” he asked.
“Yes, the fourth floor of the hotel next door,” I said, staring him right in the eye.
It was obvious that he was indeed ripe for the picking but maybe just needed a little help. So I rose from the stool, being very careful to make sure he observed the thigh of my leg with the high-tops, and asked if he’d help me with my jacket.
To my delight, he did so. And without giving him a moment to re-consider, I took him by the hand and headed for the door. His friends were literally cheering now as we walked out the door and I simply couldn’t help but subtly glance back at them and smile.
As we entered my hotel and headed up the elevator, Gary literally did not say a word. I thought to myself, “Well, either his friends think he’s a virgin and is ready for this, or they know he believes he’s gay and want that to be tested. I guess we’re about to find out.” I casually looked down at his crotch as the elevator went up, hoping to at least see some evidence that things were “picking up”. But … nothing.
“Hmmmm,” I thought to myself, “okay, don’t be disappointed. The show must go on.” When we reached my room, I unlocked the door and allowed him to enter first. Gary had an amazing tight ass. I was definitely getting wet in all the right places. But my goal was to get HIM wet … inside ME!
I told him to take a seat in a comfortable chair in the corner of the room. Gary had no idea that the “show” was about to begin. Without saying a word, I removed my raincoat, and then my black jacket. I could see his eyes were right where they should be …. on my loosely buttoned blouse.
“Gary, “ I said, “Would you like some …. (pregnant pause fully intended) … wine?” Before he could answer, I moved to the small refrigerator across the room where I had a chilled bottle of Veuve Cliquot ready and very slowly bent over to reach in for the bottle. I gave him more than ample time to stare at one of my best assets ….and made sure my tight skirt rode up just enough for him to see the tops of my thigh-highs. I pulled out the bottle and asked, “Gary, have you ever popped your cork?”
Aha! For the first time I saw some emotion. He laughed, took the bottle, and I said. “A lot of times it’s much simpler if you just screw ….don’t you think?”
Gary popped the champagne for us. I poured us each a glass and sat on the corner of the bed … kicking off my stilettos and staring at his crotch. I had the exact right amount of space between the bed and his chair to very naturally extend my right leg right to the “target area”. (No accident there in the furniture placement ….there’s a lot of planning required for a “Gay or No Gay” mission.) When I made the move with my leg, and he felt my foot slowly touch his crotch, I simply said, “Gary, would you do me a favor?” He took a BIG gulp of wine as I ground my heel harder into his crotch and asked, “Would you take off your pants?”
HA! Gary’s eyes nearly jumped out of their sockets. He obviously did not know what to say, so I clarified myself. “Gary, I want to see your cock. Seriously, do you mind?”
BINGO! For the first time, I saw signs of life in Lazarus and I nearly leapt for joy. I wouldn’t call it an “erection” per se, but there was definitely movement from beneath those trousers that wasn’t caused by the room’s air conditioning unit.
“I’m serious Gary, because I’m conducting a little experiment. I want to see what really turns a man on visually. And the only barometer I have is … well … your cock.
If I can’t see it, I’ll have no way of gauging progress. Here, let me help.”
I put down my wine, knelt down before Gary as he sat in his chair and began removing his belt. It was a little strange, as he didn’t offer any help. But he didn’t offer any resistance either. (Most guys would literally LEAP out of their pants at a moment like this.)
I removed his belt, then his trousers, and then his Calvin Kleins ….to reveal … a totally flaccid cock. Whatever I’d just seen moving inside his pants had gone back into hiding like a turtle’s head in its shell. Holy shit, I thought. This had NEVER happened to me before. Maybe Gary really wasn’t meant for a woman.
This was now becoming far more than just a challenge. I had something major to prove to myself here and there was no fucking way I was going to let this kid get out of that room without fucking me. I looked him straight in the eye, with my finger tips just lightly brushing the head of that cock and said, “Gary, as soon as I saw you walk into that bar tonight, I knew I had to have you. You are not leaving here tonight without fucking me. Is that clear?”
Well cue the Hallelujah chorus! Like magic, Gary’s cock suddenly moved and expanded at least an inch. (One small move for man but one giant leap for Gary’s cock.) And it suddenly hit me. Damn! It was my tone of voice! I gave him a taste of domination and THAT seemed to have an effect. But then it hit me, “SHIT! I NEED TO CHANGE LINGERIE!”
“Just wait right here,” I said seductively and disappeared into the bathroom. As fast as possible I removed my lacy bra and panty set and went directly to leather. I mean EVERTHING leather ….black high-heeled boots, a black leather thong and bra that virtually covered nothing, a black corset ….and … I can’t believe that clerk in the lingerie store thought of this, a black leather whip.
I knew the moment I stepped out of that bathroom that we were DEFINITELY on the right track. “HOLY SHIT!” Gary said. And that semi-flaccid cock of his literally leaped to attention. “Damn,” I thought. “Why hadn’t I figured this out before? His father had been seeing me because his wife wanted to always take control. Men subconsciously ALWAYS want to fuck their mothers. And if she was a control freak, that’s what I needed to be!
“Take off your fucking shirt,” I told Gary. And he quickly obeyed. “Now get rid of those fucking socks. I want you naked. COMPLETELY naked.” Again, he obeyed like a puppy at his first training session. “Now, lie down on the fucking bed.” Again, no problem, he was sprawled out face-up in a split second, with his cock now sticking up like a lightning rod. Houston, we REALLY had lift-off.
I slowly walked around him, not saying a word, just letting him look at me. “Damn, I thought. I wish I had brought handcuffs.” I quickly scanned the room for ANYTHING I could use to tie him down but saw nothing. I lifted one leg up to the side of the bed and ran the heel of my boot across his leg, up his thigh, right to his cock and rubbed the heel of my boot against his balls. BINGO. This kid was now hard as Gibraltar. And I suddenly realized ….my boots had laces … LONG laces.
As Gary watched me intently, I left the boots on but slowly removed the laces and used them to tie his wrists to the top of the bed frame. At first, it seemed like Gary might be a touch afraid. But when I brushed my whip gently across that cock and it literally jumped further into the air, I knew this was “exciting fear” … kind of like going to your favorite horror movie.. For the first time that evening, I thought to myself, “Now THIS is going to be fun.”
“So Gary, just keep your eyes on me for a moment,” I said as I slowly unbuttoned my leather corset. “Do you like me better with ….(and away the corset went) ….or without.”
I had now hit the fucking jackpot as Gary looked at the nipples of my tits sticking out of holes made for them in my black leather bra, “I’ll go without,” he laughed. But this time, it was a GREAT laugh. Gary was undoubtedly now having fun.
Keeping my laceless boots on, I slowly removed my black leather thong. My pussy was so fucking wet the juices were literally dripping. I just looked at Gary and asked, “You look REALLY thirsty.” I immediately then straddled his face on the bed and his tongue went to work as if he’d been ready for this for years. “OH MY GOD,” I thought. I was panting so heavily as he literally devoured my pussy that I came within thirty seconds ….and again …. and again! Honestly, I could never remember cumming this many times in a row so quickly.
What I thought originally was going to be one of the most difficult experiences of my life was rapidly turning into one of the absolute BEST! Gary was struggling to free his hands from the ties, so I whipped him and grabbed his cock so hard I thought he was coming to cum like Vesuvius!
But then I quickly withdrew. “Not so fucking fast, Gary. There is no way I’m going to let you cum until I’ve had my own fun to the max.”
I then … ever so slowly … began to circle the gorgeous head of Gary’s cock with my tongue. He literally cried out in pleasure.
“Don’t you dare fucking cum,” I yelled and went down on him so hard and fast, it was like a bareback blowjob marathon. I actually was AMAZED he didn’t cum as I must have continued going at it for at least ten minutes, using every trick in the book … light licks behind the head, heavy licks around the balls, tongue and hands working together, gobs of saliva to make it sloppy, you name it. I was conducting BBJ 101 for Gary and he was LOVING IT. But he was also screaming and writhing to get out of those laces.
I stopped sucking for a moment and asked, “Tell me something, if I untied you, what would you want to do to me?”
Without a moment’s hesitation he screamed, “I want to fuck you so bad it hurts!”
Chills literally ran up my spine. By this time his cock was so big I was almost fearful of what it might feel like. But … okay … not THAT fearful. I leaped off the bed for a second, dug a condom out of my bag and strapped it onto what was now like a fucking railroad spike. The condom barely fit.
But I DIDN’T untie him. I stood on the bed, straddling that cock and ever-so-slowly lowered my pussy toward it. When I just barely, lightly brushed my dripping wet pussy lips over the edge of his totally erect cock, he laughed and yelled simultaneously so loud I thought security would bust into the door.
“Quiet!” I ordered. “I refuse to allow you to make a sound or I will NOT move any farther downward.” He looked up at me like a kid that had just been told Santa didn’t existed.
“Good, now that’s better.” And I lowered myself more ….first moving up and down just so the head of his cock felt the inside of my pussy, then slowly … lower and lower …. until he was fully inside me … and then I began pumping … up and down … up and down with a slight twist … then again, up and down.
“OH MY GOD,” Gary said (quietly I might add). I really didn’t want him to cum yet, so I slowed down the pace, literally sat on his cock inside me, leaned way back and whispered into his ear, “So … do you still want me to untie you?”
By this time Gary was soaked in sweat and he just whispered back into my ear, “If you untie me, I’ll turn you over on your back and pump you so hard I’ll probably cum for days.”
WOW! I had to admit, THIS was a magic moment. Before even reaching climax, it was now obvious this was DEFINITELY no gay young man I had here.
I slowly moved toward the corners of the bed, untied him and OMG OMG OMG OMG!
He literally threw me onto my back and began fucking me like Secretariat at a stud farm. Within seconds, his sweat was literally dripping on my tits and he was ramming in and out of me so hard and fast I CAME AND SCREAMED AND CAME AND SCREAMED until I thought I was literally going to pass out. Then he yelled, “PLEASE TELL ME I CAN CUM NOW!”
“YES!!!!!!” I screamed. But there was NO WAY I was going to miss this edition of “Gary’s First Load.” I pulled him out, ripped off that condom, and I cannot even begin to tell you how much cum sprayed all over my body. Gary kept cumming and cumming and cumming like he’d been holding it back for years (which was probably the truth.)
I was literally COVERED in cum … from my boots to my tits to my mouth to my hair.
As Gary watched, I rubbed my hands all over my body like his cum was suntan lotion.
Gary literally collapsed into the bed beside me, rubbing one of his hands over my cum-covered tits. He obviously was deep in thought. But he didn’t have to say another word because I knew what he was thinking, “I DID THIS! I ACTUALLY DID THIS!”
I could see in his eyes that he was thrilled he FINALLY figured out the key to open his psychological sexual door. As for me, WOW, I was so wiped out I’d completely forgotten what got us there in the first place.
GARY? GAY? ARE YOU FUCKING KIDDING ME?
There was a part of me that wanted to call his Dad right away and break the news. But frankly, this sex with his son was SO FUCKING AMAZING I didn’t dare.
Gary and I laid there at least another hour, just talking. There was no way either of us would be capable of another round that night. I hadn’t felt that exhausted since winning races in my long distance track star days.
Finally, Gary looked at his watch, saw that we’d been at it nearly three hours and yelled, “Damn! My friends are going to think I was taken hostage. I’ve gotta go!”
I laid in bed watching Gary get dressed and said, “You WERE taken hostage. But wasn’t it fun?”
He just smiled, kissed me good-bye and said, “I honestly have no idea what you saw in me in that bar, but all I can say is it was DEFINITELY meant to be. I don’t know how to thank you. You’ve literally changed me … in ways I could never even explain.”
I was really tempted to say, “It was far more than mere “chance” but I didn’t dare.
I just looked at him as he left and said, “My pleasure.”
When the door closed, then … and only then …. did I reach into my purse and pull out the envelope Gary’s father had given me. I opened it, looked inside, and just smiled.
It really fucking was my pleasure.
Purely fictional story for your reading pleasure.