Chapter 14

Jeff had thought that Ann would be waiting for him in the suite, probably wearing a new negligée. That, however, was not the way the women had planned Ann’s deflowering. That might suit a mere male, but that was not the way the women thought. I might have known it wouldn’t be that easy, he realized, eyeing the clothes that Diana had laid out on the bed for him.

“Put the suit on, Jeff. Don’t even think about saying no.”

“Why are you dressed up?” he asked, noting his wife’s new dress – at least he thought it was new.

“I’m going to be serving. Everyone is. You will meet Ann in the hallway just before the big dining room. You will take her arm and escort her in to dinner. Treat her like the lady she is, just as you do me when we go out. Make her feel great. After dinner, you will escort her to your suite, and from there, you’re on your own.”

Jeff didn’t say anything for a moment, but was thinking about something else. “Baby, I wish it had been this way for you. Not the backseat of a car with me not knowing what to do. Not to say anything about getting you pregnant.”

“Well, if I hadn’t been so busy coming from your sucking on my nipples, I could have said no. Don’t put too much blame on yourself. Besides, we had a good time, and we made Arlene in that backseat.”

Jeff picked up his shorts, but Diana knelt in front of him. Taking his cock in her hand, she kissed the head and licked it. Then standing, she kissed him and quickly turned away. In a tight voice, she said, “I’ve got to run. See you in the dining room. Make me proud.”

Jeff knew there were tears in her eyes; although, she had purposely turned away before he could see them. But he didn’t know precisely why there were tears in her eyes. Sad? Wishing she had not set this up? Proud of him? Glad for Ann?

I can’t go down that road. If I get into worrying now, I could really screw this up. It would be a real irony if I got so uptight I couldn’t get my dick up. That girl would never get over it.

A little later, he was dressed and wondering if he should be looking for Ann when the bedroom door opened and Arlene walked in. She, like her mother, was wearing a black, mid-thigh dress that looked like it cost a bundle. Also like her mother, she obviously was not wearing a bra and was showing a lot of breast with the plunging neckline of the dress. Her makeup was well done – understated. He suspected this shopping trip had cost him a ton of money. He was now certain that all the girls would be dressed for the occasion.

As they started out of their bedroom suite, Arlene held her arm out. “You’re the best, Dad. I know you’ll make her remember this all her life.”

For a moment, Jeff could not speak, fighting a lump in his throat. Finally, he managed, “Fuck her brains out, right?”

Arlene put his hand inside her dress, cupping it over her breast. Kissing him lightly, she giggled and whispered, “Make her walk funny.” Sobering, she removed his hand, and taking his arm, they walked out of the suite and into the hallway.

As they reached the hall for the main dining room, he could see Ann standing there wearing a white dress that had to be the mate of the black ones that Diana and Arlene were wearing. Yes. A ton of money. But just seeing her makes it’s worth it already.

The dinner had gone off without a hitch. There was not a single giggle from any of the girls. Jeff thought they must have stayed up half the night planning and practicing. He had eaten at four-star restaurants that had not served as well, nor had the food been any better. Melissa even popped the wine cork with a flourish, poured a small amount into his glass and presented it to him for his approval, in utter sincerity. He had swirled the wine around in the glass as he had seen in the movies, tested its bouquet, and tasted it. When he gave his approval, even though he wasn’t enthused with the taste, Melissa poured for Ann, then Jeff.

Ann took it all in just as if Jeff knew what he was doing. They could have picked this stuff up at the local mini-mart, and I wouldn’t know the difference.

He noted that Ann only drank half of her glass of wine even though the meal took forty-five minutes. From time to time, one of the girls, or Diana, took pictures as the couple was served. He noticed a video camera discreetly mounted on a small tripod not too far from their table, and he suspected there was a microphone hidden in the flower arrangement. As they stepped out into the hall after they were finished, Diana took more still shots. They’re treating this just like a wedding. This is going to be a hard act to follow. What am I going to do that will equal this when we get to that suite? Shit. I’m beginning to think that I’m more scared than she is.

Glancing down at the beauty beside him, he tucked her arm in his and said, “Shall we?” while trying his absolute best to radiate confidence.

When they arrived at the suite, he opened the door and scooped her into his arms, carrying her across the threshold to a faint giggle from her. He nudged the door closed with his foot, desperately hoping Diana had not been watching when he picked Ann up and also hoping that if she were, the threshold bit wouldn’t piss her off.

Diana had been and had proudly said to her daughter, “I told you he would.” They both had tears in their eyes, but they were smiling too as they turned away with the other girls while heading back to the kitchen to discuss Ann’s “wedding.”

Jeff put Ann on the couch, then sat beside her, noticing a slight tremor in her hands as she smoothed her skirt down. Is she scared or excited? He had no idea but put his arm around the beautiful girl and kissed her forehead. “Diana tells me we have a full twenty-four hours, and this will not be the only time, either. So, we can relax and get to know each other.”

Ann looked up at him and smiled as he continued trying to relax her, “To tell you the truth, Ann, I’m a little uptight. I want this to be just the way you want it to be, and I’m afraid I might do or say something wrong,” he said, thinking a little candidness might help to calm her. “So, if you don’t mind, let’s just chat for a little while. Is that okay?”

Ann kissed him on the cheek and in a quiet voice, said, “I would like that. I’ve thought about this so many times, but now I feel somewhat foolish. I never expected your wife to do all this. They sent me to bed last night while they did all the planning. I had no idea that it was going to be this elaborate. Mrs ... uh, Diana must have spent an awful lot of money on all the clothes. I know mine cost a lot, but they kept shuffling me around when we went shopping, obviously hiding what they were doing. But I had no idea that she bought outfits for everyone. And that meal must have been catered. I’m feeling really guilty right now.”

Jeff grinned at her, hoping to set her a little more at ease. “Well, the one thing that you definitely don’t have to worry about is the cost. As you know, we came into a bit of money, and I’m never going to spend half of it. And... I’m proud of Diana. She did this with class. By the way, you do look good in that dress,” he emphasized.

Ann blushed nicely. “What there is of it,” she said while forcing herself not to push the neckline back in place as half her left breast was exposed. Said neckline went almost to her pretty bellybutton.

“Would you like some more wine?” Jeff asked, noticing the bottle on ice near the couch. When she nodded her head, he picked up the wine and the cork puller conveniently lying nearby, and started working on the cork. “I don’t think I’m as good at this as Melissa is,” he said as the cork finally gave up and came out of the bottle.

“Where did she learn to do that?” Ann asked with a nervous chuckle. “She was so professional when she opened it and poured for us. I almost couldn’t believe that was Melissa standing there waiting for you to approve the wine.”

“Search me. I certainly didn’t teach her. I’m definitely not a wine connoisseur, but from the way that cork came out, she had practiced.”

“Yeah. I thought so too. They went to a lot of trouble for me.”

“Because you’re worth it,” he assured her.

Jeff drank a small glass of the wine, and Ann drank a half glass before she motioned for him to put it back on the table. After taking her face in his hands, he touched his lips gently to hers. Then before she realized what was happening, he scooped her up, and as he stood with her in his arms again, put his mouth against hers and kissed her for real.

She responded timidly at first, then opening her mouth slightly, returned the kiss in kind. He still had not done anything with his tongue. After a moment, he broke the kiss and carried her into the bedroom where he gently deposited her onto the bed. Sitting beside her and leaning down, he again kissed her forehead. After working his way, he touched his lips in a trail around to her ear, where he spent some time nuzzling and lightly kissing her there. He didn’t put his tongue into her ear, just breathed behind her earlobe, then kissed there before slowly working his way down to her neck.

As he kissed his way past the little hollow just above her collarbone, he felt her tense up a little, and her breathing change. Ah, I’ll have to remember that place and revisit it later. While continuing to kiss his way downward, he used the plunging neckline of the dress to allow him access to skin as he kissed southward. He knew that she was expecting him to go for her breasts. Probably every boy she has been out with has either done that, or tried, so I’ll kiss between her breasts, just barely touching the beginning of their slopes before I continue on toward her stomach.

When the slit ran out and he could no longer touch bare skin, he continued downward, kissing her body through the dress. After reaching her mound, he slowed his pace, listening and feeling for her breathing. Judging from that, she was sure he was headed for her vagina. Just before reaching it, however, he swerved aside, kissing down the top of her leg until he reached the bottom of her skirt.

Again, he hesitated for a moment before kissing her leg through her stockings as he resumed his journey downward. When he gently nudged her legs, she spread them enough for him to kiss the inside of her thigh and a little of the back of her knee. He felt her tense up yet again, but after a few light kisses and licks, he continued on toward her feet.

As he reached them, he slipped a finger inside her heels and nudged them off, one at a time, while he pushed his own shoes off, before spending several minutes lightly massaging her feet through her hose. I hope those are thigh highs and not pantyhose. If they’re pantyhose, she might as well be wearing a suit of armor. He couldn’t see far enough up her legs to be certain.

After kissing the bottom of her feet, he licked them a little, but the nylon was beginning to make his tongue tingle. He wanted to lick the back of her other knee on the way up, but kissing would have to do for now. As he came back up her other leg, he hooked his fingers in her skirt and very slowly pushed it up ahead of his mouth. That got her attention.

Acutely aware of her breathing rhythm, he noticed the change as his mouth explored farther up the inside of her thigh. She shuddered as his mouth left the top of her hose and encountered bare flesh. No pantyhose. Good. As he pushed up on her skirt and followed with his mouth, she raised her rear slightly off the bed so the skirt would move. She was as subtle as if she had done it a hundred times before.

While approaching her womanhood, he wondered if he should bypass it again and head for her breasts. Maybe I should have undressed her on the way down, he thought. But I don’t want to be predictable. Breasts are always first. I’ll bet she was sure I would kiss and suck them before I kissed her center. Diana said to make her proud of me. He continued toward her womanhood. She was wearing delicate white, almost see-through, bikini panties that had a moist spot. Good, he thought. Hooking his fingers in the top of the panties, he slowly slid them down. Again, she rose just enough for him to slide them off without strain. He continued until they were on the floor, then resumed his kissing, but he detected a faint tremble now. Oh, I have your attention, don’t I? Sparse auburn hair, neatly trimmed, greeted him. As his mouth finally touched the bottom of her outer lips, she hissed and shuddered. Was that a mini orgasm? I think it was. He noted her girl smell, faint, but distinctly woman. Her hands were now in his hair as he kissed the outer lips to the top of one side of her womanhood, then down the other, being careful to bypass her clit.

When he was again at the bottom, he walked his lips up her center, stopping just short of her clitoris. Without him realizing it, she, at some point, had drawn her knees up and spread her legs wider. He didn’t know whether it was an unconscious thing, or she had anticipated him and was making things as easy as she could. This young lady was smart, after all.

At the bottom of her slit again, he added his tongue to the kissing, wiping it upward through her outer lips, slightly penetrating her inner also, producing a distinctive tightening in her thigh muscles. Finally, he allowed his tongue to swipe her clit. About a dozen swipes from the bottom of her lips to her clit did it. This is no mini orgasm. It’s the real thing, he thought. As she sucked in her breath, her bottom came off the bed, and her thighs slammed shut on his head with a pressure that was astonishing. He could faintly hear her crying out as she violently shivered while grinding her slit into his mouth.

Minutes later, as she finally started to come down, he gently sucked her clit between his lips, being careful to watch for a flinch of overstimulation. After a time, she relaxed and her thighs released. He could hear again.

“I didn’t know it could be that good. I never dreamed... , “ she whispered.

Was she talking to herself or to me? he wondered.

Her face was now highly flushed from her orgasm, and her reactions had moved the front of her dress around until her left breast was exposed past the nipple. Even on her back, the breast stood proudly in a perfect cone, with a beautiful pale red nipple sticking well up from the exact center. Her breasts and all the exposed skin he could see were also flushed.

As her breathing returned to near normal, he added his tongue to his ministrations, her hips beginning a small undulating motion. Almost immediately, there was a catch in her breathing. Multiorgasmic, without a doubt. A few moments later, she proved him right with her second full-blown orgasm. This time when she clamped her thighs together, he was ready and avoided getting his ears crushed, but she squeezed just as hard. He certainly wasn’t going anywhere. Her body went taut, rising off the bed until she almost seemed to be balanced on her heels and the back of her head. The wail she let out would do any man’s heart good. Boy, whoever takes this little lady to a motel better muffle her mouth, or someone will call the cops for sure.

He tried to hold her at her plateau as long as possible before she relaxed and then went completely limp. After glancing at her face, he decided that she was not out, but he would bet she could not say her name just now. Sliding up beside her, he took her in his arms and nestled her head on his shoulder, just holding her.

After a few minutes, he was beginning to wonder if she had slipped off to sleep when she sighed and quietly said, “Wow,” drawing the word out, awe evident in her voice.

I’ll take that as a compliment. He smiled as he noted a change in her breathing. A few minutes later, she did drift asleep, as did he.

Jeff awoke with something warm and soft against his mouth. After a second, he felt the nub rub through his lips again. Capturing the nipple, he gently sucked while moving the tip of his tongue against it. When he opened his eyes, he was greeted with a pair of sparkling green ones smiling back at him. “Thank you,” she said. “I never imagined it could be that good. Anything I ever did to myself never felt a millionth that good. No wonder Arlene never stops bragging about you.”

Inwardly, he flinched. What had Arlene not told?

As she pulled her breast back from his mouth and sat partway up, he realized that she was completely nude and straddling his stomach. He, on the other hand, still had all his clothes on, with the single exception of his shoes.

“We’re going to have to do something about that,” she said, almost reading his mind. After sliding off him, she continued, “I’ve never undressed a guy before, or a girl either, for that matter, but I want to undress you. Is that okay?”

Tearing his eyes from her jiggling breasts, he mumbled out some sort of affirmative, he supposed. He must have, since she started pulling on his suit coat.

He shrugged out of it, tossing the coat on the carpet, then the tie. My best suit. Diana will have my ass. But he wasn’t getting out of bed to hang the coat up. The teen unbuttoned his shirt, and he shrugged out of it as well. He had on a white tee shirt that she pulled up, but she got involved in running her hands through the hair on his chest and kissing his nipples. They had never been very sensitive, but he had to fight to keep his dick down, anyway. I don’t want my dick to be all the way up the first time she sees it. She has been a real joy so far, but she’s a virgin, and I don’t want to scare her.

The shirt came off, and she lay on him for a few minutes, moving her nipples through his chest hair. After locking her mouth to his, she teased him with her tongue for the first time, then rubbed her crotch against his groin. He soon realized that he could not hold back an erection with this type of stimulation, so he unbuckled his belt, distracting her.

After sliding down, she unzipped his pants and tugged them off. Momentarily stopping, she sat looking at the growing bulge in his shorts. When he started to slip the shorts down, she brushed his hands aside and did the job herself. As they cleared his groin, she froze and stared. They watched as he lost the battle. His cock finished swelling, then in a matter of less than half a minute, stood fully erect.

He could see a faint, probably unconscious, shaking of her head. “It will, Ann. A baby’s head is much bigger around, and it comes out of a woman – of course, still attached to the baby,” he said with a grin. “We have a whole day ahead of us, and we’ll take our time. Just trust me on this, please. Arlene and Diana take it, and I’m not particularly gentle with them. They even want it a little rough some of the time. I promise I will be gentle with you and go at your pace. We can stop at any time. You are the one in charge here. There is nothing that says that you can’t leave this suite tomorrow still a virgin, if that’s what you want.”

She grinned at him, her eyes sparkling. “Not a chance. I’m not going to chicken out on you. I’ve waited for this too long to do that.” Her glance locked on his cock again as she continued, “Are all men this big?”

He knew that she was aware that men came in many different sizes, but he answered as honestly as he could. “No. I am a little bigger than most, but there are plenty of men bigger than I am. Some women say size isn’t important. Others say the opposite. I think that the man caring for the woman, and doing his best to do the things that please her will have far more effect than size. My tongue never penetrated you more than a half-inch or so, but you seemed to enjoy it pretty well,” he gently chided her.

She blushed and glanced at him, then looked back at his cock. “Can I touch it?”

“Sure,” he said with a laugh, “but pull those shorts the rest of the way down. They feel weird where they are.”

While chuckling a little, she removed his shorts completely. After a moment, she slid up the bed beside his hip, before leaning over and touching the tip of his cock. It jerked, almost causing her to snatch back. While grinning at her own reaction, she gently wrapped her hand around his staff just below the head. A moment later, Jeff put his hand around hers and showed her how to stroke a man.

“The head, especially the tip, is very sensitive, also the area on the underside of the head. As I become more stimulated, I’ll be able to stand more pressure, but after I ejaculate, the head will become hypersensitive for a little while. Almost any stimulus during that time will be more than I can stand.”

“I’ve seen a couple of porn movies,” Ann said, holding his dick and looking at him. “The guys’ penises were not any bigger than yours. They may not have been as big. And the men shot their stuff on the woman’s belly or sometimes her face. It was gross to me. But I always fantasized about you shooting your stuff ... uh, your sperm, inside me.”

“Believe me,” he said while grinning at her, “shooting sperm inside the woman’s vagina is a real turn-on for me, too. But for some reason, the porn industry seems to think that they should prove that the man ejaculated. So, the guy usually pulls out and ejaculates where the camera can see it. I’ve only seen a couple where the guy shot off in the girl. When he pulled out, come ran out of her vagina. It was much more stimulating as far as I’m concerned.”

While he had been talking, she moved her hand and gently lifted his balls. Obviously, someone had told her about being cautious with a man’s balls. Either that, or she had read about it. He would bet on Arlene, or one of the other girls, though.

She has no idea how beautiful and sexy she looks sitting there holding my dick.

He knew she was responding to his manhood; her nipples were elongated and hard, poking out like pink pencil erasers. Surprising him, she leaned over and kissed the head of his dick, which promptly jumped as if it wanted more – which it did.

She grinned again and tentatively kissed around the head, then licked across the hole. He knew she had tasted his precome, but instead of stopping, she opened her mouth wider and pushed her lips around the head. Without being told to, she sucked gently and moved her head up and down a little.

Maybe all those whispered conversations between the girls were not so bad after all, he thought, realizing where her knowledge was probably coming from.

After taking her mouth off him, she looked up. “I’ve jacked a couple of boys off, but I’ve never really seen balls, other than little kids’. The guys just pulled their penises out of their pants. And I’ve never given a blowjob. A guy did his best to get me to, but I wouldn’t. I always thought of you before I went too far. I wanted my first time to be with you. Show me how to give you a blowjob, please. Arlene told me, and I’ve heard other girls – Melissa and Jennie – but I want to do it right for you.”

Now, how can I turn down a beautiful sixteen-year-old who wants to give me a blowjob? But if I shoot off in her mouth, I won’t have as much come to go up that tight little pussy. Aloud, he said, teasingly, “Well, if you twist my arm.” She giggled her sexy little giggle, and he chuckled.

“You had a great start. You can use your hand on the base of my penis to stroke me the way I showed you a while ago, while you do me with your mouth. You can put a little, or a lot, more vacuum on the head. Just tighten your lips and move your mouth up and down the shaft.”

As she put action to his words, his breath caught, and he stumbled over his instructions. After a couple of minutes, she pushed her mouth down too far and hit her gag reflex, but she quickly recovered and continued. A new female, an eager teenager, her sexy mouth encircling his dick, plus the sight of her swaying, sexy breasts, was bringing him quickly to orgasm. Her enthusiasm was growing, too, and her speed was picking up while her face flushed.

“Easy, Sweetie. If you keep that up, I’m going to put a load of come down your throat. We should, maybe, wait a while for that.”

With an audible pop, Ann pulled her mouth off his throbbing penis and looked questioningly at him, her lips slightly swollen from her ministrations to his manhood. “I thought guys loved blowjobs. Why don’t you want to finish?”

As he pulled her back on top of him, her breasts felt terrific pressed against his chest, and his dick was between her legs just below her pussy. “I would love to come in that sexy mouth of yours, but while girls can come many times, guys usually take a while to recharge and can’t come nearly as many times, either. Also, your vagina might be a bit sore tomorrow, and oral sex would be a lot easier than regular sex then.”

“So, are you going to pop my cherry now?” she teased, rubbing her nipples through his chest hair.

Boy, she surely isn’t bashful. “Only if you’re ready.”

“I’ve been ready since I was thirteen,” she declared. “I want you inside me. Jennie and Melissa tell me it’s a thousand times better than I could ever imagine. And you wouldn’t believe what Arlene says.” She blushed, but continued, “If it’s anything like the difference in orgasms...” She sighed, leaving the statement unfinished.

Jeff took her face in his hands and gently kissed her mouth while extending a hand to her womanhood. He teased her nether lips for several minutes, occasionally brushing her clitoris. After a while, he concentrated his attention on her little bud. Her mouth became more frenzied on his before she shuddered, humped her mound against his hand, and came. After eventually pulling her mouth away, she fought to get her breath, her movements slowing to a stop. He could swear she was purring as she kissed his neck. How do women do that?

“What do we do now?” she said with a sigh. “If you keep giving me orgasms, I’m going to go to sleep on you after one of them. I’d hate to wake up in the morning, still a virgin,” she declared while clamping her legs tight to trap his erection between them.

“Well, we could do it with you on top. If we do it like that, you can stop or go on as you wish. As it goes in a little and maybe becomes uncomfortable, you can stop and get accustomed to it, then start again when you feel like it. Probably, that way would be easier on you. I’m here to do anything I can to make this as pleasant an experience as I can. Again, we have a whole day ahead of us, so there’s no hurry.”

Ann sat up, straddling him just below his groin. With a look at him, she took his cock in her hand before hesitating again. “I know that. I also know that your wife is a wonderful person to let me have you for a whole twenty-four hours.”

After quickly positioning herself, she rose up as much as she could to touch the tip of his cock against her pussy. A moment of hesitation and she slid his dick through her outer lips until it lined up with her virgin hole. After hesitating, she locked eyes with him for a moment before she let a little of her weight down to push his manhood in. After a few seconds, it became apparent that she was having trouble getting the angle just right, or else her lips didn’t seem to want to stretch enough to accommodate him.

Jeff gently massaged her breasts and tweaked her nipples to try to keep her stimulated. Finally, the head popped past her lips, which caused her to suck in a breath and freeze.

“Just wait, Baby. Don’t push anymore. Give yourself time to get used to it,” he cautioned, afraid she would push too far and cause pain.

After a while, she bit her lips and tentatively pushed, but nothing much happened. With a determined grimace, she pushed harder, then still harder. She was obviously hurting some, even though his cock hadn’t gained very much – if any.

Wondering, he turned his head so he could see the bedside table and spied a tube of lubricant. Bless you, Diana.

“Wait, Baby,” he told Ann. “I see something that will help us. Rise up for a moment, please.”

After sliding partway from under her, he was able to reach the tube, then slathered the lubricant on the head of his cock while she blushed. She’s tighter than I remember Diana being. Dammit, this was supposed to be Ann’s night. It isn’t going to be much fun for her if she is hurting like crazy. “Try it again now, and Baby, please don’t get frustrated. You’ll be so very proud that you have such a tight pussy one of these days.”

She didn’t say anything, just lined herself up and pushed. His cock went in roughly a half-inch before she put some real weight on it and forced it in a little more until it hit something. He was almost ready to tell her to stop when she stopped pushing on her own. The first half-inch of his cock felt as if it were locked in a vice. There would be two people sore tomorrow, if this kept up. And he knew that her maidenhead was still firmly intact.

After pulling back, she experimented a little, then bore down harder, only for her barrier to stop his cock again. It felt as if he had hit a brick wall. Squeaking, she froze. After sitting still a moment with him trying to comfort and encourage her to take her time, she rose up a little. Looking him in the eye, she dropped herself on him with the apparent intention of ramming his cock all the way in. It didn’t work – his cock hit her hymen and stopped. She squeaked, winced and trembled as he sucked in a breath. If this keeps on, I’ll have a bruise on the head of my dick.