I had no idea what she wanted me to do, "How to you mean?" I asked.
"Firstly, let go of Mr. Pinky Dinky.... Let go of him" A smile came across her face as I opened my hands again. "Okay and put your arms behind your back... lean on your arms."
"Like this?" I asked as I leaned back.
"Yep.... And arch your back."
I felt kind of silly as I arched my back as best I could. I kept my legs closed, in an attempt to conceal my shyness.
"That's good baby..... but, can I get you to just spread you legs a little bit?"
I slowly opened my legs, exposing myself to her. "A bit more, open your legs up all the way."
I stretched my legs wide open, exposing my pink 2inch stub and my plump, tight little balls to her. I felt so pathetic and helpless. Although I was flaccid, my pathetic member jutted out: pointing up at her. It must have looked like a tube of lipstick! I could tell she was trying hard not to laugh. Her face was beet red and she was grinning from ear to ear.
"That's good. That's very good." She said as she continued to giggle to herself.
45 minutes passed and I was getting cramps. I was so uncomfortable. Not just because my penis was almost definitely getting smaller, but because my back was killing me. I must've looked so silly. The whole time she had that large grin on her face. She was taunting me. She knew what she was doing to me: to my ego, to my manhood... and I didn't find it funny at all.
The prospect of fucking her was gone. I was no longer a man in her eyes. I would be something that she'd taunt or tease; not to my face, but behind my back; which is worse and far more demeaning. I had gone from being the object of her affection, to a dickless pathetic sissy boy. Of course, these thoughts only made me more anxious and even smaller.
"Finished" she finally said after what seemed like an eternity.
I quickly reached for my boxers and put them back on. "Can I see?"
"Sure" she said as she turned the painting around.
I was in shock. She couldn't possibly be thinking of showing this in her gallery on Saturday night along with her other paintings. The painting was perfect, she had drawn me so precisely.... but without a penis, or at least what you could see.
"You, you forgot something." I told her.
"No, that was you. That's what you looked like." She said.
"But, I have no penis!" I said on the verge of tears.
"Its there, but you need to look closely. See?" She pointed to my crotch on the painting, "there is your little dinky, poking up, pointing to the sky and there are your little testies"
My eyes watered up, "That's not fair! That's not me! That's not me at all!" I protested.
"You gotta change it!" I yelled at her in desperation.
"Sorry, I don't do that. Sorry.... I think this will be a big hit at my gallery on Saturday."
Suddenly, I lost all control. I burst out into tears, I fell to my knees and begged. "Ohhh! Please no! God no! Please don't! Please! It will ruin my reputation! My life! Please no! God no! Don't expose me like this! Please!"
Moments later, I was sitting in her kitchen, fully clothed drinking a cup of tea she had made me. "Are you feeling better?" she asked.
"uh-huh" I responded, still sobbing.
"Look, I'm sorry about the painting. I didn't mean to hurt your feelings. I had no idea you'd react that way. I've never seen a guy cry before." She seemed somewhat sorry for me, but obviously disgusted.
I finished my tea and left. She assured me that my secret would be safe with her. As I left, she said, "Sorry things didn't work out between us hun, bye."
I began to think, 'If I hadn't cried like a little sissy bitch, would she still have fucked me?' Probably..... but then again, probably not.
Saturday came, and although I didn't bother to go to her Gallery opening, I heard that it went well. The big hit of the night was her painting titled, 'the frightened turtle', which was the painting of a faceless man with a really tiny penis. So, she clearly kept her promise: she got her painting, and I got to keep my shame a secret.... but it was a secret that would come back to haunt me later on.
Six weeks later, I was out on a date with a woman I had met at my gym. Her name was Claudia. Claudia was a gorgeous woman in her late twenties. Tall, athletic, blonde and leggy.
I'd been gawking at her for the past three weeks before I gathered up enough courage to ask her out; to my surprise she accepted. The evening was going well until Tina bumped into us.
Tina was there with a couple of friends having a few drinks. She spotted me, dining with Claudia and decided to come over and say hello, she was a little drunk. She took me completely by surprise.
"Hey Tim!" she busted out.
I sorta lost my cool once I saw her. "Oh, hi Tina."
"What's goin on here?" she said in a nosey tone.
"I'm on a date, this is Claudia." I told her
Claudia said hi and Tina went in to shake her hand, "This is a great guy! A nice, sensitive guy. Very sensitive. You're a lucky woman!" she said.
"Oh really?" Claudia responded.
"Is this a first date?" Tina asked.
"Yep, yes this is. Claudia and I are on our first date." I said, in an attempt of get rid of her.
"Well, I'd better go then. I'm cramping your style.... It was good seeing you again Tim" She said.
Tina turned to walk away. Unfortunately, she was behind me, so I couldn't see her. "It was nice meeting you Claudia" As she said 'Claudia' she did the small dick sign with her thumb and index finger.
In astonishment, Claudia's jaw dropped. She immediately burst out into laughter. I looked behind me, only to see that Tina was gone. "What's so funny? I asked. "Oh nothing, I just thought of something small that happened the other day...... listen, can you excuse me for a moment? I need to go and powder my nose, I'll be right back."
Of course, she never came back. The rest of the night I could hear Tina and her friends taunting me from their table. After a half hour of embarrassment and humiliation, I decided to leave.
Thereafter, Claudia spread the rumor that I was the man in the 'frightened little turtle painting'. The rumor quickly spread like wildfire, I soon earned the nickname 'Tiny Tim'.
Everywhere I went I heard giggles and whispers, mostly from women.
That's why I moved.
The End.
Birthday Weekend
It was destined to be an incredible weekend. Karen was determined to give Ann her best birthday memories ever. These two women had shared the sex lives most intimately over the years since their college days so long ago. Each knew all the wet details of all the other's sexual adventures. They had communicated continually over the years about their sexual exploits.
Now in their mature years they have embarked on a whole new level of sexual adventures together. Karen had divorced two years ago and was re-exploring her sexuality, not that there was much left to newly discover. Ann was still married to her college boyfriend but had trained him to accept and enjoy her intense sexual appetite. Her enjoyment easily became his, giving her license to explore whatever her naughtiest fantasies may demand, as long as she shared all the juicy details
Ann and Karen had developed a new, shared hobby: seducing much younger men; boys, really, legal in most states, maybe not all. Together they had developed and shared tactics for selecting and seducing worthy young men. They had both long ago discovered the secret to success... that a man, especially a hormone engulfed younger man, would do whatever was requested of him. Seduction was a no-brainer.
Each had seduced several young studs over the past two summers. Summer was a good hunting season for this with college summer break delivering young men into the grounds-keeping, pool-maintenance, house-painting fields. College boys were everywhere, shirtless and sweating in the hot summer sun as they worked at their client homes.
While Ann and Karen were twice the age of these boys, their bodies still attracted the eye of these potent young men. All the women had to do was show up in a bra
-less tank top, short shorts or casual nightgown and invite the young victim in for an iced coffee. An invitation to her in the shower was almost never turned down. It was always that easy. A young man was quickly entranced by a sexy older woman uninhibitedly showing him all possible sex play. Any suggestion either woman could make was eagerly entertained.
Ann and Karen relished sharing their exploits with one another. That led Karen to suggest a special birthday weekend for Ann, to hide away at an out-of-state resort where they could anonymously enjoy a bit of an orgy with a couple of young men. Karen actually seduced Ann into this with juicy descriptions of what Ann could enjoy if they get together with their current boy-toys. Karen teased Ann about having two horny young men fuck her brains out for her birthday. It could be a most forbidden and memorable adventure. Karen's plan was to be in charge of Ann's sex. Ann was to be merely go along with whatever Karen put before her. It would be amazing, Karen assured Ann. Karen instructed Ann where and when to show up, with Karen responsible for talking both boys into participating in the plan.
Ann trembled with anticipation, her mouth dry and her mind racing. She was actually a bit afraid of what Karen may have planned for her, fully realizing just how extreme this could turn out to be. Karen had rented for them a large suite at four-season ski and golf resort. It would be very romantic, with a private balcony overlooking the mountains and their own hot tub. Ann, of course, would know Mark since he was her current plaything and had been fucking his brains out nearly every morning after her husband left for work. It had been great fun so far, with her husband fucking her brains out every evening after hearing all the details. But she not yet met Karen's current boyfriend, making him a stranger for this sexual adventure. She allowed herself, at Karen's urging, to let this add to the excitement.
It was working, until she finally arrived at the resort. Karen met her in the lobby and brought her up to the suite.
"You are going to be so surprised," Karen giggled. Ann grew a bit fearful at this. When they entered the suite, Ann was immediately taken aback, shocked to meet not only her own boyfriend, but also Karen's TWO young lovers. "Happy fucking birthday," Karen whispered to Ann as she stood there unable to find words. "We are all going to fuck your brains out this weekend," Karen added ominously.
Three young men, shirtless, well-muscled and tanned, stood before Ann wearing self-conscious smiles as Karen introduced Ben and Pete. A flood of scenarios raced through Ann's head. "Don't worry," Karen softly told her, "I have everything all worked out for you."
They all changed and went to dinner so everyone could get to know one another. But there was a powerfully erotic tension among them, everyone knowing full well they would be spending the weekend giving Ann all the sex she could possibly handle, plus a bit more. After dinner they returned to the suite where Karen took the lead in setting the mood for Ann. There was a massage table in the master bedroom. The three boys stripped off their shirts and proceeded to strip Karen naked. They positioned Karen on the massage table where Ann watched as they proceeded to give Karen a most erotic six-hand massage, eventually culminating with Karen on her back, legs spread wide, fingers over-filling her pussy, a few in has ass, a mouth sucking her clitoris, the other mouths sucking and licking her breasts, all rocking her to one thunderous orgasm after another.
It was an incredible sight for Ann. With all her sexual adventures over the years, she had never actually watched someone had sex. She had enjoyed having her husband closely watch her fuck a young man on a secluded beach one time, but watching this was quite different than being watched. It was most erotic and she could not wait to receive the same treatment.
When Karen was finally finished, and it was a very thorough treatment, the boys all turned to Ann. It was quite erotic to have all the boys strip her naked. The boys then stripped themselves nude for her to look them over. It was a spectacular sight, three virile young men, extremely excited from their sex-work to Karen, their erections rock-solid and pressing firmly straight up against their belly. Everyone was brightly flushed with great excitement.
They led her to the table where she received a luxuriously unhurried backrub before being turned onto her back. She enjoyed another unhurried massage to every square inch before the boys finally began to focus on her sex. She likes having her nipples sucked or pulled rather firmly and the boys knew that. They had been well-coached. She loves having her pussy carefully but totally stretched wide with lots of fingers, to the very edge of too much. That was exactly where she was by the time they (finally!) began licking and sucking her clit. They each took turns bringing her to orgasm. She lost count. She was nearly passed out when they finally stopped.
She could not really move much under her own power by this point. Someone laid a towel loosely over her face, lightly blindfolding her. She felt herself being pulled down toward the foot of the massage table. Her legs were raised and held high by strong hands. Other hands wrapped firmly around her hips. She felt a very hard and hot cock rub up and down her wet and swollen labia. She had no idea who was about to fuck her. This anonymity greatly excited her as that cock slid deeply into her with one strong thrust. She felt all these men holding and cradling her as they fucked her. The thrusts were deep and powerful. He was very, very excited to fuck her. It was incredible, especially when she felt him pause and his cock begin to pulse. She felt a blast of young semen explode deep in her pussy. His orgasm was that of a very, very excited 20-year-old with excessive hormones. She realized she was in for way more than she could ever have anticipated.
The cock inside her pulsed on and on. He must have inject a quart of semen into her. She felt it running out of her and down her ass as he continued to push, pump and cum. That much semen definitely came in handy. When the young man finally slipped out of her and semen poured out, another hard young cock eagerly pushed into her. He made wet sloppy noises fucking her. Ann heard Karen comment how sexy it sounded. Ann felt relieved to discover this young stud was very much ready to cum. She was a little afraid she would quickly end up sore. But that first load of slippery semen helped and soon the second boy was crying out as he sprayed her depths with another huge load.
Ann heard Karen coach the boys to keep her legs up so her pussy would stay full as the third young man slopped into her. Ann felt like an extremely wanton slut with a room full of people there to fuck her. It was an amazingly sexy feeling. Soon they current young man was pumping her full of yet another load of cum.
Just when she thought things could not get any more sexy, they laid her back to the center of the table. She felt all those hands gather up all that semen and spread it all over her belly, legs, chest, neck, face. Keeping it mixed with just enough oil kept it forever slippery. Still blinded by the towel, she had no idea who it was taking turns licking her to orgasm as the others gave her that full frontal body massage.
She did not need to be reminded these boys were 20-year-olds and that meant they did not need much coaxing to quickly be ready to fuck her again. Karen, of course helped get each them to their sharp edge of ejaculation, to protect Ann from getting sore. It was not long before Ann had earned the right to brag she had been fuck six times in one evening. She woke late that night curled up next to Karen, her pussy a sopping mess and her entire body tacky with oily remnants of cum.
The next day was interesting. Ann was a bit concerned. Despite how careful and deliberate Karen had directed the previous day's sex, Ann's pussy was still a bit sore. But Karen had anticipated that. She really did think of everything; so sweet of her. After a day of golf and shopping. At dinner Karen had embarrassed them all by openly discussing their previous evening's sexual adventure. They all blushed, especially when Karen went on to describe her plans for the coming evening. Ann giggled when Karen told her she was now officially a slut after taking on the equivalent of six guys. She coaxed everyone to agree with that observation. She went on to announce that a slut could not be a full-blown slut unless she had sucked off a similar number of cocks in one even
ing. Everyone was really embarrassed now.
Back at the room, Karen took Ann to the bedroom where they both dressed in very sexy tiny nighties. Karen assured and encouraged Ann that she would enjoy tonight as much as she had last night. Ann said nothing in reply, too engrossed in the strange excitement that now enveloped her. They returned to the boys in the living room. There, Karen fired up her laptop and plugged it into the widescreen TV. They all watched the video Karen had made of the Ann's fucking the night before.
Ann was shocked and a bit angry. But that soon passed when Karen suggested the boys give the girls a little show. Soon there were three naked men on the sofa with towering erections. Stroking their cocks as the girls sat at their feet for a close view. After a few minutes of this, the girls were soon sucking and licking those cocks, swapping back and forth among them. Karen asked the boys to let them know whenever they started to get close to cumming. When Pete was the first to speak up the girls teamed up on him, Karen massaging and licking his balls as Ann swallowed his erection. The girls soon coaxed a very loud orgasm from him, Ann swallowing his gift to her. Watching all that got the other boys close to the edge. It took very little effort to make first Ben then Mark to cum in Ann's mouth.
The boys were, for the time being, spent. But the women knew this would be temporary. They made their way to the hot tub. Karen knew what would revive the boys quickly. She brought a pair of vibrators to the tub for them to play with. All that boy cumming had excited the girls. And the girls knew how the boys would respond to their own little sex show. Ann resisted, feeling too shy for what Karen was planning. But Karen was now fully in charge. Ann had by now totally given herself over to Ann's control.
It did not take much coaxing for Ann to join Karen on the edge of the hot tub to explore a bit of vibrator play. It was, after all, to get the boys revved up for more sex. And both women by now were themselves dying to cum. It was an incredible show for the guys watching these two women stimulating themselves with their sex toys. In no time, they were totally lost in the lust of running the vibrators in and out of their pussies and over their clits. Ann was still quite inhibited about it, at least until Karen allowed herself a thunderous loud climax. That was all Ann needed and she was cumming before Karen's orgasm was passed.
Filthy Daddy's Taboo Erotic Sex Stories Page 80