Mary and Tom had several casual dinner dates with just a modest amount of passionate kissing. They talked about being a little more intimate but between Mary's strict upbringing and their lack of privacy it was just talk.
Becoming a bit frustrated with the status quo, Tom had suggested they indulge in some talk about their fantasies and how they might enjoy each other in the future. In describing how he envisioned the future Tom had made it clear that he would be the leader in their sexual explorations. With that in mind he'd outlined how he would want Mary to dress on their dates. He knew her wardrobe was very conservative and he had made it clear that as her budget permitted, he expected her to buy sexy lingerie and more revealing clothes.
Mary said she would try to do that. They had then discussed a little of what he had in mind. Mary volunteered to go shopping for lingerie soon.
On the day after that date Mary followed through to shop for some lingerie- not underwear. Tom had made a point to distinguish the two. Mary had never worn anything but cotton underwear. If she'd ever suggested buying a bra or panties in anything other than white cotton her mother would have thrashed her as a sinner. Tom had said that he understood her upbringing but she was a woman now and should embrace that. According to him a woman's partially hiding her curves and intimate areas in sexy lingerie was feminine and very appealing to men. Tom had said he couldn't explain it but a woman in nice lingerie was frequently thought of as sexier than the same woman fully nude.
Mary thought that didn't make any sense but surely Tom knew more about men's likes and dislikes than she did. She wanted to be feminine and sexy for Tom but shopping for her first lingerie was still going to be a challenge. To lessen her embarrassment in the store, Mary did some Internet searching. She first searched "silk lingerie" and was shocked by the prices. She knew average women didn't pay $1000 for a bra but from what she saw, that figure wasn't unusual. She clicked over to other sites and realized that she'd been naive. Changing 'silk' to 'silky' in her search made a huge difference in the available bras. Now she was simply overwhelmed by the countless styles, prices, and manufacturer's claims.
It was embarrassing but Mary realized she needed to seek help from one of her roommates. She didn't want multiple girls involved and so had to bide her time until only one or two of her closer friends would be present. She finally got her suite- mate, Nan, alone and explained her dilemma. Following an hour of blushing conversation, Mary had at least some understanding of bra styles she'd never heard of much less worn. She learned there were styles you bought for everyday wear that were comfortable. They could easily be sexier than her white cotton basics but you were buying these for yourself- not for your boyfriend.
Nan said there were other styles you'd probably buy with your man's desires in mind rather than your comfort. Knowing Mary's concerns about her modest breast size, Nan suggested that Mary check out bras with push-up pads or- going the other way- bras that were sheer and would tease her boyfriend with some nipple exposure. Mary blushed furiously at the thought of her nipples being visible through the fabric of her bra. She almost died when Nan explained that since Mary had prominent nipples, she was sure Tom would enjoy being teased by the nice nipple bumps that the bras would allow to show in various tops.
Nan laughed as she realized how embarrassed Mary was at what she'd said and then felt guilty for referring to Mary's nipples as if she'd been studying them. "I'm sorry if I shouldn't have mentioned your nipples. It's just that I've seen you in your nightgown without a bra countless times. I've been a little jealous since it's been obvious your nipples are a lot more prominent than mine. Mine are flat- almost inverted. A lot of guys love the sight of big nipples and from what I'm told their fingers and mouth can please a girl in ways I've barely experienced."
Mary mumbled that it was okay but she was still clearly uncomfortable. She hesitated and finally said, "Growing up I was told to always make sure my nipples didn't show. I was told that it was sinful to excite men by letting your nipples or cleavage show. I didn't have cleavage to worry about but as you said, my nipples would try to poke through my clothes so I wore gauze pads or Band-Aids to cover them."
Nan said she understood how strictly religious teachings frowned on most aspects of sexuality. "It's not for me to give you religious advice. I'm simply saying you have great nipples that most men would be attracted to like magnets to steel. If you insist on covering them then I'd suggest a push up bra. It can make your chest look very inviting. You're big enough to generate nice cleavage with the right bra."
Mary blushed again. She said while her breasts had grown from the previously flat profile, they were still small. Wearing a push up bra seemed like false advertising, she said. "If you wear a bra like that and then you get serious enough with a guy to let him see your breasts, won't he feel cheated?
Nan smiled and said, "I guess if men were totally rational that could happen but I think most men are so happy to get the woman's top off they're very delighted with whatever they uncover. Besides, in your case, your nipples should more than make up if your breasts aren't as big as expected." She paused and then added, "In case I didn't mention it, even though I've never seen you topless I'd love to have bold nipples like yours."
Nan reminded Mary that Mary should be sure to buy panties that matched each bra or were at least similar in terms of sexiness. Granny panties were not ever to be worn when she was with her boyfriend whether it was a date or simply as a co-worker. "The right panties will make you feel sexier and that will be transmitted by how you walk, talk and interact with guys," she said. As an afterthought, Nan said, "I don't want to know what you do or don't do but make sure your pubic hair is at least trimmed to fit inside your sexy panties- no hair sticking out." Mary blushed but nodded her understanding.
The discussion ended with Nan suggesting that Mary should go to a boutique lingerie store to get measured so she'd confirm she was buying the right size bra. She could buy multiple bras there if she liked the store or could go on-line to buy there. "Assuming you're past the religious hang ups, buy a sheer bra and a push up bra; your guy will love to see you in both."
Mary thanked Nan for her help. She made up an excuse to end the exchange and secreted herself in her bedroom. As soon as she had privacy, she opened her blouse and insinuated two fingers inside her left bra cup- assaulting her big nipple and gasping in arousal at the resulting excitement. She visualized Tom being aroused by seeing her erect nipples and then his fingers assaulting them as she was doing. It was hugely exciting.
As her arousal grew, she imagined Tom's fingers on one nipple and his lips and tongue attacking the other breast. She'd never experienced a mouth on her nipple but her "imagination ran wild- it would feel so great-exquisite sexual pleasure. She pinched and twisted her nipple harder as she imagined her other nipple being bathed in saliva as a horny man lustfully teased it. She gasped and her whole body stiffened as her excitement redoubled. Within seconds Mary was in the throes of a huge orgasm.
She could barely move as her body felt like limp pasta. Her mind recovered faster and started to visualize dressing for a date with Tom in in a sheer bra under tee style shirt. She'd be terribly embarrassed as her protruding nipples poked out against the fabric but she was sure he'd love the blatant look. She'd need to go on-line to find the bra. Nan had described them as having seamless cups- being made of a thin woven fabric. Once she had the bra, she'd need to experiment with wearing it under different tops in the privacy of her suite. When she was comfortable enough to wear it for a date, she'd need to control their destination- somewhere a bit dark like a tavern would be the best. Dating was more complicated than she'd previously thought.
