Hard Hal in Bermuda
by Pamela
"Oh my God Hal, not more lingerie!" Debbie was holding up a pink negligee.
Hal winced at his wife's irritated remark. They were sitting next to the modest Christmas tree in their living room as they opened presents.
"Every Christmas you buy me some ridiculous negligee or bra or thong or something - all covered in lace - I wear it once to make you happy and then you never see it again. Right? Am I right?"
"It's just honey that..."
"Am I right?"
"Yes, but..."
"It's because I don't like that kind of frou frou. I don't want to hurt your feelings Hal, but I've told you a hundred times already that I'm not that kind of woman. I don't crave flowery girlie type stuff."
"It's just that, and you know I've said this a hundred times, Cosmo says it keeps marriages alive and fresh. It's on every list of top ten things to spice up a marriage." Seeing her expression he added, "and I'm not trying to imply that our love making is dull or I'm bored with it. It's just a way to reach even higher. To progress to another level."
"It certainly sounds to me that you're dissatisfied."
"But Debbie, there was even an article in Redbook that I read at the checkout counter at the supermarket that said that surprising your husband with a new naughty item of lingerie is the number one thing that turns men on."
"So you need turning on? Is that what you're saying?" Debbie had a pretty nice figure. That was one big reason that Hal wanted her wearing sexy lingerie.
"Of course not. You know I find you beautiful. You have a wonderful body. I think the lingerie would look so good on you. You would seem so super feminine. It's because you're so beautiful that I fantasize having you in sexy lingerie. It's not the other way around. Women who've lost their shape look terrible in lingerie."
These last remarks made Debbie smile. "Look Hal, we are really going around and around in circles on this. I am flattered about what you said, but I just can't dress myself up in silly clothes to satisfy a fantasy of yours. It leaves me out of the fantasy. I don't get anything from it myself. In fact, I don't need any extra fantasy. I just like feeling our naked bodies together. That's plenty."
There was silence for a minute or two until Hal said, "well, to be honest I'm not surprised by your reaction. You're pretty darn consistent about your disdain for lingerie, though I keep hoping you'll change your mind one day. Anyway, I bought you a few more nice presents that are probably more for you than for me."
"Oh Hal, I love you," Debbie said and went over to him and gave him a kiss. He smiled at her and they hugged. He reached over to the tree and picked out another box for her to open. Before she did so, Debbie said, "you know Hal, I don't really mind if you wear the lingerie you buy for me. God knows you love it so much. I guess I really wouldn't mind, as long as you just wore it around here, and not outside the house."
Hal turned red. "Really, Debbie, do I give you the impression that I want to wear it. I'd look ridiculous in it and I'm sure you'd make fun of me. It would be a big turnoff to you."
"Hal. It's OK. It's no big deal. I mean I realize that you'll never look as good in it as I would, but it's not going to turn me off. I might laugh. I can't promise you I won't. But I would not be laughing at you. Just with you."
"Well I suppose I'll have to think about it," Hal said. If the truth be known her suggestion had launched an enormous flight of fantasies in his mind that he had only very rarely ever allowed himself to think about. Wearing women's clothing had long been an attraction for him but he also had strong feelings of shame for having the desire. The result was that he put a tight lid on any thought or fantasies he might have about it lest he find himself actually cross-dressing.
They finished opening presents and then settled in for a long weekend. A snow storm that had been brewing intensified and they knew that they wouldn't be able to leave the house anytime soon. After lunch they gathered up the presents to put them where they belonged. Debbie handed Hal the pale pink negligee that he had bought for her. "Here, this is yours."
Hal looked at her and shook his head. "Thanks. I don't really know when I would ever wear it."
"Hal, that's up to you. You can also fish the other fancy stuff you bought me the last few years from my panty and bra drawer. It's yours!"
"Thanks," Hal said a bit sardonically.
He went upstairs to their bedroom carrying the negligee. He opened up Debbie's lingerie drawer and took out a bra, panties, lacy all-in-one, lace-top stockings, garter belt and two slips that he had bought her previously. She had looked so incredible in the bra and panties he remembered not being able to hold off his climax the one time she wore them while they made love. He had been so happy that she had gone along with the fantasy, but then had become disappointed that she avoided ever wearing the sexy clothes again.
Debbie was in her study putting away a beautiful lamp he had bought her. He came up to her and said, "well I think I'd like to see how the negligee and other things fit. Is it really OK?"
"Hal, you don't have to ask my permission. I honestly don't care if you want to play with the clothes. I know how much they mean to you."
He went back to the bedroom, undressed and put on the bra and panties. They were of a delicate, filmy pink material that was silky to the touch. He was a bit surprised how comfortably the bra fit. He would have thought that it might not be well suited to his male body, but he was of fairly slender build and in fact sort of a clone of Debbie in terms of height and weight. The feeling of the clothes was electrifying. The way the bra hugged his sides and back and the tangible presence of the lacy cups over his own breasts made him dizzy with desire. He felt intensely feminine. And he eagerly put one of the slips on, a pink full-length slip with lace along the hem.
Hal was hot. He felt happier than he could ever remember. A cascade of emotions overtook him. He felt sultry and sexy. He felt coy and delicate. He wanted to desperately be in bed with Debbie. He sashayed to her study and quietly walked in.
"Hi Debbie," he said timidly.
She turned around and looked at him. "My my look at the pretty girl.
Don't you look ravishing!"
Hal laughed. "Can you come with me?"
"Where?"
"To the bedroom?"
"Not right now, it's kind of early for that."
"I'm feeling so happy. Is it wrong of me? Are you upset?"
"Hal. It's OK. Chill. But you'll have to wait."
"OK Honey, I'll wait."
Hal found a book to read and curled up in front of the fire.
It was probably the happiest day Hal had spent in his life but he was scared to tell Debbie that. Yes, she was a big part of his being happy, but he felt if she knew how much joy he felt in pretending he was a woman she would be upset.
Debbie truly did not act like she was put off by his dressing up and she even found him a skirt and top to wear during dinner since she saw that he was a bit chilly wearing just underwear when he sat in his chair near the window of their large eat in kitchen. That Debbie could be so kind to him made him love her even more than he already did, if that were possible. He told her several times during the evening how much he appreciated her openness, her matter-of-fact attitude toward his need to dress up, how uncomplicated she made the whole experience for him. She said more than once, "Why should I object. There is no victim here. You do look kind of funny but also kind of cute."
The "kind of cute" part he loved hearing and it made him feel like he really was a cute girl.
After dinner he couldn't stand how much desire he felt for Debbie so he went up to her again as she worked in her study and put his arms around her from behind and hugged her. He nuzzled her ear with his face and said, "I think this is a good time for lovemaking."
He sat down in her lap and put his arms around her neck and kissed her cheek. "Am I crushing you?" he asked. He was wearing just his bra and panties and he batted his eyes coyly.
Debbie laughed once and said, "Oh my God, what have I unleashed! Such a
floozy!" She gave him a tongue kiss with such force and energy that he
nearly swooned. It was like he really was a delicate young thing and
she was a powerful man. He moaned in great excitement and Debbie kissed him a second time. As he moved his tongue into her mouth she grabbed it hard with her mouth and he had to fight to keep her from yanking it so far that it hurt. She put her arms around him and he felt her hand hold onto his neck and she squeezed him and kissed him for a third time.
"I think my sexy little girl friend is ready to be taken," Debbie said in an imitation pirate accent.
"Oh my mighty pirate!" Hal said in a falsetto voice.
Debbie laughed and said, "get your hot butt in bed and get ready to be rammed right up to the hilt."
They laughed and laughed and Debbie chased Hal to the bedroom where she playfully threw him to the bed, took off her slacks and panties and jumped on top of him. His penis was hard as a rock, and his mind reeled with excitement at the wonderful exhilaration of having discovered this unsuspecting capacity of Debbie to play act a fantasy with him.
While she straddled him with her legs pinning his arms to his side, she took off her blouse and then her bra. Her voluptuous breasts dangled and swayed above him.
"Now my little maiden, we take off your bra and panties and we get you ready for your punishment!"
"Oh no!" Hal said in a high girlish voice.
Debbie forcibly pulled down the arm straps of his bra and turned him on his side and undid the back hooks and yanked the bra off. "Oh my God what huge bazooms you have! You're like a freaking cow. Oh baby my shaft is going to stuff you clean up to your tonsils!"
"Don't, don't," Hal said. He was in pure ecstasy of excitement.
"What are you going to do about it?" Debbie said as she pulled his panties down past his bottom. His penis sprung up in front of her. "We might be at full mast, but you're not going any where!" Debbie grabbed his penis in her hand and said, "what a beautiful pussy you have! I've got to feast on it!" She slid down over his lower legs and aggressively took his penis in her mouth and began sliding it in and out making sure her tongue kept it lubricated.
"Don't take me! I'm a virgin," Hal said, "I belong to the convent."
Debbie took his penis out of her mouth, "I prefer virgin meat. Yum. By the time I get through with you, a convent is the only place you'll be safe." She resumed sucking on him.
"Honey!" Hal said a few minutes later. He was getting close to coming.
Debbie stopped. "You better wait until I've taken what I want or you'll walk the plank!"
"Yes, my pirate! Please take me now!"
Debbie planted her vagina on top of his rock solid penis and pushed down and up forcing him into her to greater and greater depth. She was more excited than Hal could remember. "Oh my God Hal!"
They frantically made love and reached a height they had never been before. It was almost scary how explosive the pleasure had become and how violent their mutual orgasm that was accompanied by Hal screaming at the top of his lungs. In the aftermath Debbie collapsed slowly down on top of him keeping his penis inside her and he put his arms around her and they fell asleep together.
The next day Hal wore the bra and panty under a slip and when Debbie saw him she said, "all the time? Is that what you want?"
Horrified at the implication of what she was saying he took off the clothes. During the remainder of the day Debbie did not seem to notice that he had switched to boy clothes, but later that night she said that she did not want to give him the impression that he shouldn't cross dress. It just had been a kind of surprise to her how much bigger his interest in crossdressing was than she had suspected. She suggested that he wear his bra and panties under his boy clothes and if she didn't see them she wouldn't care about them at all.
To Hal this was a big step back from the previous joyous night he had spent with Debbie and he didn't know what he should do or say about it. He didn't want Debbie to take it the wrong way and be angry with him.
For the rest of the week he wore the bra and panties under his boy clothes. In some sense it was enough to satisfy his desires, but he also could not forget how wonderful it had felt on Christmas to be dressed like a girl all day long.
Life in the neighborhood got back to normal after a few days. The streets got plowed and Debbie and Hal were able to go to work and do errands. For New Year's Eve they had been invited to a party at the Mason's who live a mile away in the same development. As they got dressed for the party Hal looked with some envy at the sexy black dress Debbie was going to wear. He watched as she put on her panties and bra and then starred with rapt attention as she put on her pantyhose.
"I wonder what it feels like to wear pantyhose?" he said. Her legs were beautiful and he couldn't help but note that with stockings on they were even more beautiful.
"You want to wear pantyhose also?" Debbie said.
"To be honest, I'd like to try wearing them. There is something really sexy about them."
"You find sex in everything Hal," Debbie said, "but go ahead and wear my pantyhose if you want. I bet they'll fit you."
"Maybe later after the party," Hal said, "I certainly wouldn't wear them in public!"
"I should hope not," Debbie said.
"I'm sorry honey, but I honestly can't tell if my wearing your clothes bothers you or not. On Christmas you seemed to think it was great and we had so much fun together, but after that...you know."
"You're right Hal, I guess I have been giving you mixed messages. I think I began worrying that you'd want to become a girl, like I mean all the time. Have a sex change operation. You know the whole works. And then where would I be?"
"Oh honey," Hal said. "I would never do that to you. I don't want to be a woman; I mean I don't harbor feelings of wanting to be a woman. It's just that when I look at the pretty things that girls can wear I feel a kind of envy - I want this also. If you would wear them it might be enough for me. But, to be honest, this is probably even better for me. I feel more closure."
"I'm glad you're so honest with me. I think in a lot of marriages the man would never confess such things. It's great that we have this communication." Debbie said.
"But how do you really feel. So far I think that some days it's OK for you and on others it's not. I think I need rules to follow. Like specify dress up days during which I could be a girl and the other days I'd be a boy."
"I think that's too much control for me. I still don't really know all my feelings about this. For example, I loved dominating you last week but if I close my eyes and have a fantasy it's probably more about you being kind of strong and solid and someone who can protect me."
"So I guess the bottom line is that we're going to have to keep on seeing where this goes."
"Yes, that's a good way to describe it. Let's just let each time happen on its own and we'll see what goes from there."
"It's like the main thing is keeping fantasy in our relationship. Not just any one particular fantasy, but fantasy in general. It'll keep our lovemaking fresh. It'll keep us in love. I love you Debbie."
"And I love you Hal. Yes, let's always try and keep fantasy in our marriage."
Of course it occurred to Hal later that every time he gave lingerie at Christmas it was meant to spark a fantasy. Evidently there were some fantasies that would fly and others that would not.
It was not much later that Debbie and Hal set off to Bermuda for a week long holiday with their friends the Mason's, George and Pamela, and two other couples they were close with: Ed and Edith and Dan and Marie. The trip had been planned for a long time and was an experiment of sorts. The four couples played a monthly bridge game together and sometimes they also got together for golf. The idea of a trip together had come up by accident in conversation and it turned out that everyone unanimously agreed that it would be a very fun thing to do.
They had booked four rooms at a 5 star resort on Bermuda Island. Golf at a championship course was free to guests of the hotel and making tee reservations was the first order of business when they arrived. They arranged for the men to play on several days and on others the ladies would join them and they would play as couples. When they weren't golfing or sitting poolside the women planned visits to local museums, gardens, shops, and nature preserves. They left open one day where they would all do something special. After making some inquiries at the hotel they discovered that para-sailing was available and they quickly agreed among themselves that that would be the perfect activity. Both Hal and Debbie were particularly pleased since they had long shared a desire to find out what this sport was all about.
The days passed quickly and the couples grew to very much enjoy each other's company. Hal had brought a bra, panty and a short cute peignoir with him and hoped that maybe he and Debbie would fall into another great fantasy such as they had had a few weeks earlier at Christmas time. As luck would have it, on the evening before their planned para-sailing adventure, Hal could tell from long experience that Debbie was "in the mood" for lovemaking which meant that she would more than likely put a lot more into it then she would on the nights when it was his suggestion to make love. It wasn't that Debbie resented him initiating sex, but Hal was sensitive enough to know when Debbie was eager and when she was not.
The thought of Debbie being hot invariably made him even hotter and he was beside himself with glee when Debbie casually mentioned to him that he was welcome to wear his ladies things if he wanted to that evening. Rapturously happy, he put on his bra, panty and nightie after his shower and came to Debbie in the semi-darkened room and lay down next to her. She was watching an Arnold Schwarzenegger movie on television.
"Now that's a man," Debbie said as Arnold's great arms grabbed a huge machine gun and blasted away at some bad guys. Hal cringed slightly. "And here is my little girlie man," Debbie said and laughed.
Hal debated whether or not he ought to take off the clothes. Debbie's remark did not seem totally to be meant in fun.
"My girlie man is named Hayley. She is so soft and curvy," Debbie said and Hal felt her hand touch his cheek and then slide down his front stopping to feel inside his bra and then continue down toward his panties. "Pretty Hayley. You're so hot. I bet Arnold would love to grab you with his big powerful hands. Maybe I should call him up and see if he wants to come here. I suppose I could loan my girl to him, as long as Arnold gave her back to me after he is done with her. What would you like Hayley? Should I call Arnold and have him come over?"
Hal felt excited. He wasn't so sure about having Arnold in the fantasy, but every time Debbie called him Hayley he felt his member get harder. "I don't know," Hal said.
"Do you like his muscles?" Debbie starred at him.
"Yeah," Hal said.
"I've heard his you know what is monstrous in size. Would you like to play with it Hal?"
"Sure," Hal said.
Debbie looked down at Hal lying alongside her. Her hand found the top of his panties and she slipped her fingers inside the waist band and slid them around toward his inflamed penis gently touching it as if to check how erect it was and then she slid her hand back toward his rear end and gently held onto one of his ass cheeks. One of her fingers pushed down slightly into his crack and he felt his penis surge with pleasure. "I keep forgetting what a pretty ass you have Hayley. From what I've heard Arnold likes his girls with pretty asses."
Hal moaned imperceptibly. He could see the flickering TV image of Arnold who now had a rivulet of blood on his forehead. His gun sporadically fired at enemies lurking around in a factory. The sleeve of his tee shirt as it stretched over his huge bicep had a small tear in the fabric.
"Look at those arms Hayley," Debbie said, "I bet girls like you just swoon over big manly arms like that. Am I right? Don't you just love real men, men with arms like steel, men with muscles that you can touch and feel how hard they are? You know that Arnold's cock is not the only part of him that's hard, though that's the part that he'll let you make hard. No, his biceps are hard all the time."
Hal felt woozy.
"C'mon baby girl. Tell me if you want Arnold," Debbie said in a soft voice, "and I'll call him."
Hal was mesmerized by what Debbie was saying and he prayed she would never take her hand off his rear end. "Sure, call him," he croaked.
"OK, you asked for it," Debbie said. She punched some buttons on the phone. While covering the mouthpiece she said, "it's ringing." She waited a few seconds and said, "Oh hi Arnold. It's Debbie." Pause. "I'm fine." Pause. "Oh that is so funny." Pause. "I'm calling because I have this hot girl here with me who's got an unbelievable ass who just confided in me that she has a crush on you."
Looking down at Hal Debbie said, "Tell Arnold you want him to come."
She held the phone out toward Hal so that it would pick up his voice.
"Come Arnold," Hal said.
"Come Arnold?" Debbie said. "That's how you ask him? If you want him to come you'll have to tell him why he should come. Tell him Hayley."
"Arnold, I want you to come because I, I, I,..., I really want to make love to you."
"Good grapes, Hayley, lots of girls want to make love to Arnold."
"I'll do anything. I mean I'll let you do anything to me!" Hal said toward the phone. A small part of his mind prayed that Debbie wouldn't get freaked out and jump out of the fantasy.
"Now you're starting to talk," Debbie said. "What would you do?"
"I'd, I'd, I'd,..." Hal said. He didn't know what to say. He saw Debbie shake her head slightly.
"Arnold, are you still there?" Debbie said. Pause. "Hayley, he's losing his patience."
"I'll suck on him, I will, I'll do it great. He'll never forget it!"
Hal was panting. Debbie moved her hand off his butt and drew one of her fingernails along his torso and up to his chest. The finger hit the underwire of his bra and burrowed under it lifting the bra. She slid her hand inside the bra cup and over his breast.
"You hear that Arnold? Hayley wants to suck on you big time." Pause. "Yes Arnold, she's got lots of experience sucking cock." Pause. "Her tits? They're pretty darn gorgeous. Big, well formed, no silicone, no sag. Just pure feminine perfection." Pause. "Her nipples? They look just like the nipples on a rubber baby bottle."
She paused and said into the phone, "Yes, maybe the best jugs I've ever seen." Pause. "Arnold wants to know if he can stick his cock through your tits." She held out the phone again toward Hal.
"Yes, Arnold. Really anything you want. You can play with my breasts and my vagina and I'll suck on you and we can make love. Anything you want. I'm yours completely. Just come. Please come."
While he said this Debbie squeezed his nipple, rubbed his breast, and then methodically did the same to his other breast and then slid her hand back down his back and into his panties, over his ass, between his legs until she had his balls firmly in her hand. The pleasure was making Hal frantic.
"Arnold says he'd probably want you to spend awhile with his cock. He's had a hard day. He needs to lie down and relax and have someone devote himself to his cock."
"Yes, I will. I'm happy to. Tell him to hurry up and come."
"You heard that?" Debbie said. Pause. "Hayley, Arnold says not to worry you can have him for the evening and even until the morning."
Hal grunted. On the TV Arnold appeared to have won his fight. At least he was wearing a well pressed suit and looked cleaned up and unruffled.
"What do you say to Arnold," Debbie said to Hal.
"Thanks?" Hal said.
"Arnold, Hayley says thanks. She's wearing a bra and panty right now and it would not be an exaggeration to say that she is really juiced up. She's wet everywhere it counts." Pause. "Hayley, Arnold says to stay juiced, he's coming right over." Debbie hung up the phone.
"Now you have to wait for Arnold. I'll help you get ready. Come with me." Debbie got up and went to the bathroom and Hal followed her. There was a vanity with two seats and Debbie sat down and told Hal to sit next to her. The lighting was bright and Hal felt self conscious in the peignoir, bra and panty. Debbie took out her makeup case and found a long gold tube of mascara. "First mascara, then some eye shadow, lipstick and blush. Arnold says he wants you to be as pretty as possible. While a cute ass and some nice tits is a lot, it isn't everything."
When she was done putting make up on Hal Debbie said, "You wait in the bathroom until Arnold shows up. He'll call to you and you'll then know he's here." Debbie left the bathroom, closing the door behind her. Hal looked in the mirror at his face. His eyes looked bright and feminine, his cheeks glowed and his lips looked full and pink. His panties were struggling with the inflamed member inside. He could feel his heart beating hard in his chest. He wondered if he had gone too far in the fantasy. He didn't think he really could ever have sex with a man, but as Hayley, something inside himself desperately wanted to be devoted to Arnold's pleasure.
He heard Debbie opening and closing the dresser drawers and the door to the closet. Then there was footsteps coming toward the bathroom and he heard Debbie say, "Hayley, Arnold's here, come on out."
Hal opened the door and Debbie was standing there wearing his man's blue jeans, a blue man's shirt and his hiking boots. Her hair was pinned back. There was something inside her jeans that bulged out behind the zipper a good eight inches. Her arms were crossed across her chest and her fists were clenched.
"Hayley?"
"Arnold?"
"You can see I'm excited about meeting you. I really dig your beautiful ass and lovely tits." Debbie had a slight Austrian accent saying this.
Hal laughed and Debbie cracked a tiny smile and then recovered her serious look. "Are you ready to begin?"
"Sure!" Hal said.
"Take off your peignoir but leave on your bra and panties. You look awfully sexy in them. Just like Debbie said you would. Then get on the floor."
Hal took off the peignoir, put it on a chair and sat down on the floor.
"On all fours and face my cock!" Debbie said.
Hal leaned forward putting his hands on the ground and pushed up onto his knees. He looked up at Debbie and saw she was pointing at her supposed cock. He crawled over to her and looked straight ahead at the bulge.
Debbie flexed her two arms as if she was a body builder. "See these muscles?"
Hal nodded.
"Do they make you shiver?"
Hal nodded.
"They're not like your girlie arms, Hayley. They're the real thing. You may kiss them." Debbie crouched, grimaced and flexed her biceps while Hal rested his lips on each one in turn and gave them a small kiss. They were a lot harder than he expected and he wondered if they were even harder than his own.
"You may also check out my cock. There's plenty there for you to work on." Debbie planted her feet apart and stood looking down at him.
Hal reached out and touched the bulge with his fingers. Expecting to feel something hard like a shampoo bottle he was surprised to find out that it was compliant. It felt like a real cock.
"I want you to kiss it," Debbie said.
Hal pushed his cheek against the bulge. This was not exactly what he was expecting. He couldn't see where Debbie was headed and it made him worry.
"Not nuzzle it. Kiss it. Take it out and kiss it. When you're done kissing it, you can suck on it." Debbie walked over to the bed, sat down and leaned back against some pillows.
"I can't get to it," Hal said after he crept across the floor and sat between her spread legs. What in the world did she have in there he wondered.
"Hayley, you must be a lot dumber than you look. There's a zipper and a button on my jeans. Open them."
"I don't think I should," Hal said. This was getting definitely into a place where he wasn't sure he really wanted to go.
Debbie slammed her legs together trapping Hal's face between them, with the bulge in her pants an inch from his eyes. Besides being startled by the ferocity with which she did it, it had hurt his cheeks.
"Ow, Debbie." Hal said.
"Debbie? Who's Debbie?" Debbie pressed her legs together even tighter and Hal said, "Arnold. I'm sorry Arnold."
"Damn right it's Arnold. Did I hurt the girlie man?" Debbie said. "Let me level with you Hayley. We had a deal. You're going to live up to your end of the deal whether you like it or not. Now unzip my fly, take out my cock and start making me feel good."
The last part she said with some anger and Hal winced at the forcefulness of her inflection. He felt his penis get hard, harder than it had been. He gingerly unzipped the fly of her jeans and then undid the pants button. As the jeans came apart they revealed white cotton Jockey shorts bulging out from the presence of the mystery object within.
"You've got underpants on. How can I do anything?"
"Pull them down dummy," Debbie said.
Hal took the underpants by the band and yanked them down revealing the presence of a huge, lifelike penis sticking up from where Debbie's vagina was. It seemed to be held on by some straps running around her back and legs. The penis was a very high quality imitation. Hal could see blue veins drawn on it and a variety of natural colorations. Where in the world did she ever get it he wondered? Was this whole evening planned in advance?
"What are you waiting for? Kiss it. Suck it. Worship it. I don't want to have to hurt you."
Debbie leaned back and Hal began kissing the penis. The penis was odorless and tasteless. It seemed to be made perhaps of some sort of silicon with a thin plastic cover. This wasn't anything he had expected and he worried that in the morning Debbie might feel some disgust for his willingness to play with the penis. He looked up at her face. Her eyes were closed and she seemed to be completely at ease. He began putting the penis in his mouth. He slid his mouth over it, first a little bit and then as far as it could go. His own penis felt like an iron rod between his legs. Every time the artificial penis filled his own mouth he felt a sensation of swooning. The experience was revealing something about himself that he hadn't known before. It was scary and after a few minutes of performing fellatio on the penis-like dildo he wanted to stop. He let the penis out of his mouth and eyed Debbie again.
Without opening her eyes she said, "don't stop. You do it so well."
Hal continued and Debbie said, "feel my balls also. You can also lick them occasionally." The dildo had two realistic balls inside a mock up of a scrotum. When he put his hand on the balls they gave way and he could feel them moving around. "That's good," Debbie added and she let out a soft low moan.
He kept sucking the penis for a while until Debbie told him to roll over onto his stomach. "I don't want to get you pregnant, so we do it this way."
"My stomach? I don't get it."
Debbie raised a hand as if to slap him and he cowered. She said, "turn onto your stomach. I don't like hitting girls. But if you're going to be at my disposal then you're going to be at my disposal. Comprendez vous?"
"Yes, Arnold," Hal said, "I'm sorry." He turned onto his stomach and Debbie straddled his back.
"That's a good girl," she said. "I know you're pretty innocent, but trust in me. This might hurt a bit at first but it won't hurt for long." Hal felt the dildo hit against the left cheek of his rear end and then land on his crack.
"What are you doing?" he called out in panic as he realized what Debbie had in mind.
"Don't you worry about it," Debbie said again in a thick Austrian accent.
Suddenly Debbie forced the dildo forward and it impaled on his rear hole. Hal yelped in pain. "This isn't a good idea Debbie. I don't feel safe. I want out," Hal said.
Debbie stopped what she was doing, reached around underneath Hal and felt his penis with her hand. It was hard. It was hard like an iron bar. "You're such a hypocrite Hayley. You're liking this. Anyway you can go ahead and scream or beg or whatever, I'm not stopping until I damn well want to stop. Got it?"
"I said I want out," Hal said.
Debbie jerked the dildo forward again and it moved up another quarter inch into Hal. Though Debbie had put some lubricant on the dildo it was a very tight fit and caused Hal more pain than pleasure. "Stop," Hal said. He felt tears coming.
"It won't hurt so much if you relax and spread your legs a bit more. I know I've got a very big dick but we can do this much more easily if you cooperate. The more you protest the harder I'll have to push."
Hal tried to turn around but Debbie grabbed his shoulders and shoved him back on his stomach. Quick as lightening she rammed the dildo further into him. "Ow, Debbie, the pain is terrible!" To be truthful after each push the pain shot up and then subsided as his muscle expanded.
"I think I'm making some good progress. The fattest part will be in soon and then it's all downhill from there."
"No, Debbie you're going to ruin me. Cut me. I'll never be the same. It's not fair. How can you do this to me?" His words were increasingly frantic and he started to cry.
"Holy mother of God," Debbie said and pushed once again into him.
"Owwwwwwwwwwwwww," Hal wailed hysterically. His own penis remained rigid but was folded in a painful position by the weight of Debbie sitting on his buttocks.
"Hal you're a frigging girl. You know that?" Debbie took one more painful thrust and then pulled the dildo out. She undid the straps holding it to her and took it off. Hal heard it hit the floor with a thud as Debbie threw it across the room.
"Turn around," she ordered and Hal swiveled around underneath her. As soon as he was in position Debbie hopped forward and thrust her vagina in his face. "Now you suck on Arnold!" she said. Hal smiled with relief that she wasn't going to force the whole dildo inside him. He loved her vagina and particularly liked the chance to lick on it until she came. Following a more normal pattern in their love making it did not take Debbie long to reach several orgasms. When she was done, she slid back and mounted his penis.
"It's not as hard as before," Debbie said.
Hal felt the erection fading. "I don't know what's the matter," Hal said.
It was getting difficult for Debbie to keep his penis in. "I know what the problem is," Debbie said.
"What is it?" Hal said.
"I'm going to put my penis back on and this time I'm not stopping!"
"No don't," Hal said in alarm. He could feel his penis take a big jump up in size as he said this.
"Bingo!" Debbie said and once again she was able to pump up and down on his newly erect penis. "You see Hal," Debbie said as she moved quickly up and down on his shaft, "you really are a girlie man. In real life. You need to be controlled by a strong woman. You're weak. You see yourself as a pretty, delicate girl. You know that you can never stop me from doing anything I want with you and that makes you hard. Hard Hal."
"That's not true Debbie," Hal said.
Debbie stopped moving her hips and looked down at him. "OK, let's find out exactly how big a man you are."
"What do you mean?"
"You don't like the dildo up your ass do you?"
"No," Hal said.
"OK," Debbie said as she climbed off him. "Get up Hayley, go over there, pick up the dildo and strap it on me. We're going to resume where we left off."
"That's ridiculous Debbie. I told you it hurts me. I don't want to go there in this game."
Debbie walked over to Hal and stood over him, "get up girlie man and do what I tell you."
Hal, half-heartedly got up.
"Go over there to the dildo."
"No, I won't," Hal said. He raised his hands to protect his face.
Debbie grabbed his wrist and swung him around capturing his arm in an arm lock. Hal struggled to stop her but found that he didn't have the strength or skill to get out from under the hold. "You're hurting me Debbie."
"The more you fight me the more it's going to hurt." She forced him to shuffle across the room toward the dildo and when he was in front of it he reached down and picked it up.
"You're going to break my arm," Hal said.
"Yes, I might have to. It all depends on you. Now strap the dildo on me."
"Debbie, this is ruining our marriage. This is..."
"Shut up Hal. I love you. I care for you. But look at your frigging hard on. Your words might be saying one thing, but your hard on is saying another. I choose to go by your hard on and its telling me you're going to strap the dildo on me and I'm going to resume plugging you with it."
There was no hiding his colossal erection that stuck out from his panties. The helplessness of his situation gave him the urge to cry and some tears fell down his cheeks as he knelt in front of Debbie and put the contraption back on her. She wiped the tears off of him with her hand and said, "You are emotionally like a ten year old girl." The comment made Hal sob, but he continued working until the dildo was on.
"Stand up with your back to me and bend over," Debbie said.
Hal slowly turned around and bent over holding onto a chair. Debbie came up behind him. "That's a good princess, but bend over more. Hal did as she said. He trembled waiting for the dildo to hit his bottom. He looked back at Debbie from between his legs and saw her putting some lubricant on the dildo. His view of her was partly blocked by his massive erection that had a mind of its own.
"I'm so mixed up I don't know anything any more," Hal said.
"It's very simple Hal. You do what I tell you to do, I won't hurt you and you'll have no problems."
"Do you respect me?" he asked.
"Spoken like a true bimbo," Debbie said, "now here we go!" She came up on him quickly. With one hand she grabbed his side while the other guided the dildo toward its intended opening. When it was firmly seated on it she held his sides with both hands and started jerking the dildo into him. The first quarter inch was easy and Hal thought he might even be feeling some pleasure. Then, in rapid fire succession Debbie forced her hips in toward his bottom three times which rammed the dildo a good inch further into Hal and he yelped in pain. "Stop wiggling, you're going to knock it out," Debbie said. Thus impaled in him Debbie waited patiently. "See how the pain subsides. You'll get big enough to take all of me in there if we just go along carefully." She gently rubbed his sides and the cheeks of his ass. "My pretty Hayley," she said, "I just love your ass. It's so soft and feminine." Her hand reached around his leg and rubbed his inner thigh and then grabbed his cock. "My, oh, my, is it possible to get any bigger than that? It's a freaking elephants cock," she said, "and as hard as ivory." She rubbed up and down on his penis and Hal felt a blast of pleasure that took away whatever pain he had in his bottom.
"Oh, my lord Debbie. I can't believe how that feels."
"Good," she said and then without warning shoved the dildo up in him another half inch. "That was a good one!" she said while Hal burst into tears from the huge sudden pain in his bottom. While he wailed she said, "by Jove I think we're past the worst part. Now it'll be all pleasure, but we'll wait a little bit. Just relax my little girl. Your Arnold knows exactly what's best for you."
"Oh Debbie," Hal said, "you've hurt me. I feel hurt. I have no control!"
"There, there, sweetie. Just relax and you'll be just fine. There's no blood. No blood at all. We haven't done anything bad to your sweet bottom. Your pride is a little hurt, but I assure you that you're going to enjoy me having my way with your rear end, just as soon as we get you fully acclimated."
"I'm tired of bending over," Hal said.
"Relax Hal. Now I'm going to go in and out slowly. Back and forth. Since you're as stretched out as much as you need to be this is going to be pretty easy. If you cooperate it won't hurt at all."
Debbie pulled the dildo back a little bit and then pushed it in. "Very good Hal. Now a little bigger orbit." Debbie swung her hips back pulling out the dildo and then forward putting it further in. "See that, we jumped in another inch. About four more inches and I'll have it in to the hilt."
Hal was speechless. The feeling of the dildo sliding into him was overwhelming. He felt filled up and weak. His arms could barely hold up his body as he crouched. "Debbie, please stop. Won't you?"
"Just a wee bit more honey. Let me ram it all the way in now," she said. She pushed hard and the dildo slid all the way in. "Yes!" she exclaimed. "Now out," she said and she slid it out, "and in," she said and pushed it in. "Now faster and faster Hayley. This is every girls dream. Arnold filling you up and taking every last bit of you for his own pleasure."
Debbie grabbed his penis once again. It was of monstrous size. She had lubricated her hand and as she made love to his bottom she was able to slide her hand up and down his shaft. Hal was frantic. Between the battering on his rear, the feeling of being filled up right to his chest by the large dildo and Debbie's expert attention to his penis, he felt he was on the verge of losing consciousness. He sensed he was building to an incredible orgasm and he started screaming with pleasure, "Arnold, Arnold, thank you, take me!" He finally burst into orgasm with his cum flying every which way and Debbie hanging on stroking his penis to get out every last drop. When his orgasm was spent she pulled the dildo out of him and Hal collapsed onto the floor next to the bed. In a half stupor Hal heard Debbie go to the bathroom. In a few minutes she came back without the dildo on and she gently helped him up and directed him into the bed. He lay his bottom down tenderly on the bed and stretched out. She lay next to him and held him and gently rocked him. "My pretty baby," she said. "You've done so good tonight.
"I love you Debbie, I hope you still respect me," he whispered.
"Don't worry Hal. You can't help being yourself. You are what you are and I do love you."
The next day the four couples met to arrange their para-sailing excursion. Hal walked a bit cautiously and was well aware of his bottom. It was sore and hurt a bit when he sat down. Despite that Hal was determined to enjoy para-sailing and was excited that the opportunity was finally at hand. When the group went to the concierge to find out where they needed to go, they discovered that one of the boats was out of commission and so only half the group could go para-sailing that day.
George said, "How much do you ladies want to go? I know Pamela is not too enthusiastic."
"George is right," Pamela said, "I'm quite happy not to go. I still haven't done all the shopping I want to do here."
"I feel the same way," Edith said. "I could just as well shop."
"But I want to para-sail," Debbie said, "I was really looking forward to it. What about you Marie?"
"Sorry Debbie I agree with the other girls," Marie added, "I love the shopping here."
"So it's decided," Ed said, "the men will go para-sailing. Let's get ready."
"Wait a minute," Debbie said, "not so fast. I really want to go. How about George, Ed, Dan and myself going? Hal, can go shopping with the girls. He can buy himself a new bra or slip. They have some great European lingerie shops here. Hal, you have my permission."
All turned their eyes on Hal and his face turned bright red.
"Debbie?" he said.
"There's nothing to be embarrassed about Hal. So you like wearing women's lacy underwear. As you know I don't mind and I know you'd like a new matching bra and panty set. Will you girls help him find what he's looking for?"
George, Ed and Dan glanced back and forth between themselves and then at Hal and Debbie. "While the two of you work this out," Ed said, "we'll get our suits on and we can meet back here in fifteen minutes."
"Great idea," George said and the three men walked away.
"Debbie, how could you?" Hal said.
"Don't be so shocked Hal. It's just the truth and you know it. Why shouldn't our friends know the truth about you? You're a girlie man Hal. I don't mind. I don't mind at all. I'm not going to leave you. You don't have to worry about that."
"But still Debbie, letting our friends know all about me?"
"No big deal, Hal. Is it girls?" Not waiting for the ladies to answer she said, "you run along with Pam, Marie and Edith. Buy yourself a pretty bra. A pink one. I know you love pink. You'll take good care of him won't you girls?"
"Sure Debbie, whatever," Marie said.
"Good, I've got to change," Debbie said and rushed off.
"Come on Hal," Edith said. "We know of a very nice shop. What exactly do you want? Matching bra and panties? They also have some lovely dresses. Come, we'll make a day of it."
Edith took Hal's hand and he walked with her and the other ladies to the hotel exit and then toward the shopping district.
"That Debbie is a character," Marie said, and the three women laughed.
The End
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