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Back at home after meeting a new woman in Las Vegas Bill couldn’t wait to see her again. Unfortunately, he lived near Milwaukee and she was in Chicago. It wasn’t a huge distance but it would make dating somewhat cumbersome. He would need to drive about an hour and a half each way which made staying overnight the only practical way to see her; that meant a portion of two days would be devoted to each date. They each had business and social-group commitments making it a little difficult to find matching open weekends. They spoke on the phone repeatedly but couldn’t schedule an actual date for several weeks.
Their first date since Las Vegas was coming up. Bill had a business meeting on Saturday morning but was able to leave by 1PM. He’d agreed to call Missy when he’d checked into his downtown Chicago hotel. He was then going to drive out to her suburban apartment to pick her up so they could spend the balance of the afternoon together. They had agreed that she’d dress casually and bring dressier clothes for dinner. She’d change in his hotel room.
As he arrived at his hotel he wondered if she’d wear sexy lingerie under her casual clothes. He couldn’t expect a corset or garter belt but he hoped she’d dress in something sexy. They’d had planned on a driving tour of the city since she was familiar with Chicago and he wasn’t. He hoped that she’d let him undress her back at his hotel and that they’d have sex before getting dressed for dinner. Based on their encounter in Las Vegas he assumed she’d wear a corset for the evening. Actually that was much more of a certainty than their having sex. On their first date she’d teased him and ultimately gotten him off but she’d made it clear that she had sexual limits that he’d have to respect.
In Las Vegas s she’d expected him to rub himself off using her ass crack but her corset had gotten in the way. She had ultimately given him a blow job but the BJ had been almost a medically necessary release since she’d teased him for so long. She’d been adamant that they couldn’t have sex and she’d even tied his hands behind his back to keep him under control. That had been their first date- a fact she’d mentioned several times in explaining the limits she was setting. Bill hoped she had more relaxed morals for second dates.
Bill checked in to the hotel, called Missy and used his car’s GPS for the twenty minute drive to her apartment. She was outside waiting for him when he arrived at her building- carrying a carryon bag and a garment bag. Her hair looked radiant in the sunlight and her skirt was short enough to give a suggestion of her great legs. He noted that she was wearing a navy blue pencil skirt and cream colored tailored blouse. A hint of cleavage was evident where the first three buttons of the blouse had been left open. It was just enough to remind him that there was a pair of D cup breasts waiting to be discovered. She looked great and he told her so. They kissed briefly and put her things in his trunk.
Once in the car Bill surveyed Missy’s calves and detected stockings. His cock twitched. Since she’d told him she never wore pantyhose stockings meant she was probably wearing a garter belt. Based on what she’d said that in turn suggested an ensemble of sexy lingerie. He thought his chances of getting laid before dinner were looking up.
Before driving off Bill’s eyes couldn’t help but check out Missy’s chest. Her top wasn’t obscenely tight but it was cut to follow her body which gave a clear impression of her large breasts and nice overall body. She wasn’t thin but if she was at all overweight by today’s standards it was perfectly distributed to form a very sexy hour glass body. The little bit of cleavage revealed by her blouse wasn’t enough to be exciting but did make the observer think about what couldn’t be seen. All in all she looked delicious to Bill.
Missy caught him looking and said, “If you’re trying to see if I’m wearing a corset, common sense should tell you that’s not likely in a an outfit like I’m wearing. A silk blouse is more commonly worn with a silk or soft cup bra. Mine isn’t silk but it’s a relatively thin fabric in a demi cup style. Don’t drive off the road but at a stop light you can check out my nipple bumps in the thin fabric of my blouse. I usually try not to have any nipple show but I thought you’d like it.”
“Thank you. You’ve gotten to know me very quickly.”
Bill drove around the city following Missy’s directions. She pointed out the typical tourist attractions and most notable buildings. At virtually every traffic light he turned to enjoy the small bumps in her blouse and to savor mental images of what she’d look like without the blouse and bra. As he drove he spent a fair amount of time glancing down at her exposed lower legs. After an hour Missy suggested they end their tour and stop in the lounge at his hotel for a glass of wine. Bill readily agreed.
They soon found themselves sitting across a tiny bar table. With sunlight streaming through large windows the room was well lit which gave Bill his first good look at Missy’s nipple bumps. He didn’t say Kütahya Escort anything- fearful that she’d become embarrassed and want to cover up. For the same reason he tried not to stare at her chest; short glances would have to suffice.
It didn’t take long for Missy to become aware of where his eyes kept returning and then to remember how her blouse had looked in the mirror when she’d gotten dressed. Looking down she could see that the bright light made her nipples seem even more prominent. She blushed but quickly calmed. It was very unlikely anyone she knew would be in the hotel as her apartment and workplace were both in suburbia. She decided to use her chest as a tease and not be timid about it.
When she next saw Bill’s eyes descend to her chest Missy pulled her arms back to push out her chest. The thin fabric went taut over her large breasts and her nipples poked outward proudly. “Like what you see,” she asked?
Bill nodded and said, “Absolutely. I couldn’t drive and stare at your chest; this setting is much nicer. Your breasts look great. Might I suggest we finish our wine quickly and adjourn to my room? I’d like to examine your nipples more closely.”
“Not so fast,” replied Missy. “You seem to forget that this is only our second date. I think I also mentioned that I like to tease. Putting those concepts together there will be some strict limits on your in-room lust. I’ll let you kiss me and fondle me through my clothes if you want. You can even take off my blouse and skirt but that’s it for a second date. You can ogle me in my lingerie and I’ll probably let you give me an orgasm orally but you have to respect my limits.”
“For someone with a corset fetish you certainly are conservative.”
“I don’t have a corset fetish; I simply like to wear them. As to the limits it’s not religious morals or anything. I remember from high school that the slutty girls got no respect. I don’t want to be thought of as ‘easy’. In addition, I love foreplay and know how horny men tend to skip over it. I think you should enjoy me thoroughly in my lingerie before enjoying me without it.”
“Okay. I can accept that. I’d love to enjoy you in lingerie Can I at least assume that tonight will count as our third date and not a continuation of the second?”
“Yes. That’s what I had in mind. Different rules apply to third dates.”
When they arrived in his room Missy insisted on hanging up her dress, unpacking and freshening up in the bathroom before allowing Bill to have any physical contact. He spent those few minutes hoping her rules weren’t too strict. She hadn’t tied his hands so that suggested much more freedom than in Vegas.
Finally Missy re-entered the room and moved close to him. He embraced her and they kissed passionately. His hands roamed up and down her back as his body pressed against hers for the first time. His cock sprang to full erection from the contact- a fact that her abdomen must have felt.
Bill loved how she felt. She was not fat but certainly not thin either. The contrast to his typically skinny past dates was erotic; Missy had a woman’s figure rather than a girl’s. He couldn’t wait to feel her ass but disciplined himself to only let his hands go slightly below her waist. He loved how her breasts were softly pressing against his chest; her tits were a world better than anyone else he’d dated.
Missy broke off the kiss, stepped back about a foot and unbuttoned two more buttons on her blouse. She pulled the lapels of her shirt slightly- allowing Bill to get a much better view of her cleavage. Bill’s eyes drilled into her upper chest and he said, “Very nice.” In his mind he was saying that those were the biggest most succulent tits he’d ever seen up close. Remembering the peak he’d had of her nipples in Las Vegas his mind was visualizing how spectacular her tits would be when she was naked. His cock twitched and hardened further at the thought.
Missy moved back against him and initiated another passionate kiss. Their tongues dueled and her tits were plastered against his chest. Bill loved her actions and was truly intrigued by her teasing. She seemed to thrive on being blatantly sexual one moment and then chaste the next. She certainly gave the impression that if he remained patient he’d eventually have a hot lover. He decided she was worth the wait. While patient he decided to push things a bit. His hands cupped her ass and he gently caressed that area for the rest of the kiss.
Missy seemed to kiss him more passionately after his hands grabbed her ass. At least she didn’t recoil from his advance. As the kiss came to an end Bill instinctively lowered his face to Missy’s neck and kissed her there. His mouth kissed lower and moved to enjoy the upper reaches of her breasts. Bill was highly aroused by touching her breasts and laughed inwardly at his reaction; he was acting like an inexperienced teenager. He was almost giddy as his mouth moved lower and his tongue explored the top edge of her bra without being pushed away. His cock was rock hard. He again mentally laughed at himself. Would Kütahya Escort Bayan he cum in his pants when he finally had a nipple in his mouth?
Bill backed off a few inches and brought his right hand to the buttons of Missy’s blouse. “May I,” he asked?
“Yes. The blouse and skirt are removable this afternoon. Leave the bra on; you can play with my breasts through the bra. My panties can come off which will allow you to use your mouth on my pussy. After that I thought you could get off using the crack of my ass as I suggested in Las Vegas; if that doesn’t work out I’ll find another way to take care of you.”
Bill was frustrated at not being allowed to remove her bra but dared not complain. He removed Missy’s blouse and skirt. He liked the demi-cup bra as it left a large amount of each breast uncovered. He could see the color of her areola through the bra and each cup displayed a tented bump evidencing her large nipple. Although covered by the bra Bill could get a good sense that her breasts were beautifully large and round.
He extended his hand to fondle her left breast. She moaned with arousal as his hand caressed her and slid over the bulge of her nipple. His cock throbbed in response. It didn’t take long for his fondling to become more aggressive. As he squeezed her breast it was evident that it was natural which elated him. He could have accepted such great tits if they had been enhanced but the look and feel of natural couldn’t be beat. Missy might just be his fantasy woman- molded by nature to his idea of perfection.
Her panties matched the bra; he thought the style was called a brief but the leg openings were very high cut so the overall look was sexy. His hands roamed over her newly exposed body and he told her how good she looked and felt. His hands also explored her panty covered ass and hips. The panties were nicely tight and slippery under his roving hands.
His arousal increased and he felt compelled to kiss her passionately. The kiss was periodically interrupted by his telling her how sexy she was and how her teasing was driving him crazy. He asked if he could remove her bra and suck on her nipples. She said no. She reminded him that she liked to tease and loved his lustful reaction. She said she would have been insulted if she hadn’t driven him crazy.
Bill grabbed Missy’s hips and walked her backwards until they reached the bed. He helped her lie down on the bed. He grabbed the waistband of her panties and slid them down and off. She lifted her ass in obvious consent. He then gently spread her legs so he could crawl between them. His mouth explored each inner thigh while his hands fondled her ass and thighs. Her excitement grew noticeably with his attention.
Bill’s mouth moved closer to her pussy but then took as detour to her Venus Mound where he pressed his face against her pubic bone. She lifted her hips to grind against him. He insinuated his hands under her ass and fondled her ass while running his mouth over her shaved mound. Each of them was excited by their new intimacy.
Bill then lowered his mouth to her pussy and explored her outer labia with his lips. In seconds Missy’s arousal seemed to re-double and it took only a few more seconds for Bill’s tongue to probe into her- touring her inner lips. Missy ground her pussy against his mouth as his tongue probed deeper.
“My clit,” begged Missy. “Please play with my clit.”
Bill pulled his mouth back just enough to say, “Patience is a virtue.”
“I’ve been patient for a month since we first met. Please love my clit.”
Bill redirected his tongue to the right side of Missy’s clit and tightened his grip on her ass. Missy gasped. Her hands grasped at the bedsheets. Her body tensed and then went through several spasms as a huge orgasm ripped through her. Bill continued to tease her clit for about 15 seconds – enjoying Missy’s being helplessly wracked by pleasure. When she recovered the needed muscle control her hands grabbed Bill’s head and pushed it down toward her feet to break off the contact.
“Enough…please, no more,” she panted. “Give me a minute.”
Bill savored the moment. His ego loved being able to satisfy a woman to the point that she’d push him away. It was the ultimate compliment to his skill as a lover. He gradually pulled away from her pussy and knelt on the bed between her feet.
Missy watched his cock bouncing in the air. She thought fleetingly of taking it in her mouth and giving him a nice wet blow job but decided to defer that. She’d stick to her planned schedule. Knowing his answer in advance she said, “So are you ready to fuck the crack of my ass? There’s no corset in the way this time and you have your hands-free so I think it should work. I’ll get you wet and then lie on my stomach, okay?”
Bill said, “As you can see my cock is more than ready.”
Missy leaned up and used her mouth to drench his cock in saliva. He knew this wasn’t intended as a BJ so he held still. Missy then took a pillow and placed it near her hips. She moved to her hands and knees and Escort Kütahya then lay down over the pillow to raise her ass. Bill knelt behind her and lowered his cock toward the crack of her ass. He leaned forward and used his arms to support his upper body- lowering his cock into the crease between Missy’s ass cheeks. As soon as he was in position he thrust upward and then pulled back. In Las Vegas he’d been unable to keep his cock properly positioned but now it seemed easy. He was fucking her ass cheeks and it felt good. In addition to the pure physical pleasure it was kinky. He looked forward to having her pussy but this was a damn good substitute.
Missy teased by saying, “You like my ass, don’t you? If we stay together you’ll eventually be in my ass. That’s a hot thought, isn’t it? Of course, I’m not ready to let you do that yet. Tit fucking is nice. You can think about tit fucking me while you rub between my cheeks.”
Within a minute Bill’s cock was erupting onto Missy’s back. The tension in his body eased and he had to use every effort to support himself. His body wanted to simply collapse onto Missy’s back but Bill assumed that wouldn’t go over well with her. He mustered his strength, lifted himself and flopped onto the bed beside her.
Missy said, “Well. That was much better than Las Vegas. When you’ve recovered could you get a facecloth and wipe off my back? “Bill did as she asked. He brought the hotel robes out and they each put one on.
They each had a bottle of water and agreed that showers would be needed before dinner. Missy made it clear these would be individual showers and that she required privacy for hers. They agreed on a schedule and watched the TV news until Bill’s designated shower time. Missy told Bill that she expected him to help her dress but only to the limited degree she’d specify. When he was done with his shower Missy took over the bathroom while Bill dressed and then killed time.
She eventually emerged from the bathroom. Bill could see she was naked except for small black panties and a bra. By the large amount of breast flesh displayed above the bra Bill assumed the bra was in the push-up style. He could feel his cock stiffening as he took in the sight of her breasts being displayed for him.
Seeing the lust in his face Missy told him he could look but not touch. She approached him and exhibited a short corset which she said was called a ‘waist cincher’. It had a set of laces up the back and was split in two at what Bill understood was the front. Missy wrapped the waist cincher around her waist from the back. Bill was intrigued as she connected the clasps up the front to connect the two halves of the garment. She struggled a little to close the clasps but was soon corseted from the bottom of her bra to the mid-point of her panty-covered Venus Mound.
She turned away and asked him to assure the back of the cincher was flat and to tuck in the laces. She teased him by saying usually she’d need his help with corset lacing but the cincher was tight enough already. Bill dropped his eyes and found her whole ass was exposed below the cincher. The black fabric set off her pale flesh dramatically.
She then taught him how to put her stockings on and clip them to the garters. This took some time since it was his first experience with stockings and she stressed the need for care to avoiding runs in the fabric. He enjoyed spending the time in close contact with her long well-shaped legs. When he was done he was tasked to add her shoes and close the small buckles on their double straps. He noted the thin heels seemed to be about 3 inches high- a look he found very sexy. Closing the straps to lock the shoes on her delicate feet was a big turn on for him.
Missy put on her dress- merely asking Bill to close the long zipper. As the dress closed over the waist cincher Bill was already envisioning how hot it was going to be when he unzipped her later. He couldn’t help but wonder what reduction in limits she’d grant for their third date.
The dress followed her body’s shape quite well. Seeing it from the rear Bill could picture the ass cheeks he’d just been admiring. He couldn’t resist reaching out and fondling her ass with both hands.
Missy stepped away and turned saying, “I thought you were a tit man. I picked this dress for you with that in mind.”
Bill took in the front view and smiled broadly as he saw the dress’s V neck framed the deep cleavage offered by her breasts and the bra. Somehow the dress made her mounded breasts even sexier than they’d seemed when she was just wearing the bra. He said, “Wow. You look great from the front and back.”
Dinner was over an hour of foreplay. Bill stared at Missy’s breasts off and on throughout the meal. He felt he no longer needed to be subtle; a woman who wears a push up bra and low cut dress can’t complain that her horny date appreciates the display. For her part Missy blatantly teased him. She called his attention to how the cincher made her sit very straight which pushed out her chest. Reminding him of her large nipples she said the push up bra had them well covered. “They’re stick out about a quarter inch at rest,” she said. “I’ve sewn some pads into most of my everyday bras so they don’t show through my clothes. When I’m aroused I’d guess they’re about a half inch long. I’m guessing you like that image.”
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