[The characters in this storyline are based on real people I've known and real problems and attitudes they had. Of course, names, locations and specifics have been changed to protect the guil ... ummm, innocent.
A big part of this story is teaching a prude to do things she should already know, but didn't know she didn't know. She was effectively a virgin, so I guide her thru many 'firsts'. Beyond the supervising, the action gets very hot and is full of surprises.
This story line was a chapter in the bigger story of Sue, but is totally stand alone. The initial story, Out of The Closet is here.
I'm curious what you, our reader, think about using the diary/memory schema, so please vote and comment. ]
Sitting in our open sunroom with my partner and two intimate, female, friends, Sue, Reggie and Lynn, I read from the CD backup of the old diary I stumbled across. We were all in it! We all knew our parts and bits of the others', but I'm the only one who had the whole story. Reading it brought back many vivid, touching and stimulating memories of some major intimate changes in our lives and the lives of some folks we helped. I'd already reread about Sue's breakout in the library, but this section was mostly about her sister's life change and genuine emancipation. It began:
Sue was still giddy about all the exposure she's had in the last two months. The Library Fund Raiser was huge and became her bridge to a more relaxed and honest marriage. Still, I don't know how many novelties I can provide or how often they should be or if I should get fixated on that, so we may need to talk.
Three weeks after our 'party of 5' gathering, Sue began asking for ideas for another daring exposition. I had already thought about a few to surprise her, but I need these planned events to be at least eight weeks apart so I can deal with them. In between, I expect to help with surprise flashing and impromptu 'accidents' to keep up the novelty. But unless we start arranging 'theme parties' with total strangers, she can't keep up the virtuous/bad girl pretense she enjoys. We can't let her addiction rule our marriage either. I don't remember 'organizing sex parties' among our vows. Maybe we should amend them.
//Sue, you aren't going to be upset by any of these transitional recollections, right? Never mind, I'll just read. //
"If we start looking for strangers, we'll have to figure how to stay healthy, so how about we delay going there? OK? We have a few more small groups of friends to play with, but have you ever considered partying with family? You don't want to strip for your mom and dad, do you? Is that too kinky?"
"We'll have to ask around for details about health precautions with unknowns. Um, no I never considered family unless you mean in-laws maybe. Mom and Dad? Are you kidding?"
"Yup, I was. And I hoped I found a place neither of us wanted to go. Can you imagine? I thought we could break the ice with Lois and Joe. He's always trying to peek and grope you, so I bet he'd be interested. But, Lois is a problem. If you're even interested."
"I don't see Lois letting loose like that. Having some fun with them can be very interesting, but Lois won't even TALK about sex or nudity. You've seen her blow up over TV ads that just implied nudity. Flashing Joe would be fun, but flashing Lois publicly would be VERY entertaining for us all. Can you imagine how bright red her face would be? Who else could we entertain?"
"I'll have to sleep on that. I wonder what Lois would say about what you've been up to? HA! She would be a huge challenge, but one that I'm not sure I want to tackle. You know how harsh she can get."
Yet, curiosity got the better of me so, the next day, I contacted Lois by email to feel her up, ... uh out, with usual social trivia. She was a little surprised to hear from me since we'd only had an 'acquaintance friendship' relationship. She's pleasant, but could suddenly become very cold and distant. We exchanged a few casual emails and I eventually let slip just a hint of what Sue was doing, and the surprisingly great effect it had on us. She and Joe had been having problems for most of their eight year marriage, so she was interested in why and how our relationship had recently changed for the better.
I always had to be extra careful of what I said and how I said it, so since she didn't rush away or swoon, I had to assume something had happened that let her listen more than usual.  She had let on that they were on the rocks again and something had to change or she WAS giving up. After three days of rapid emails, curiosity got to her and she called me. It seems I was about to take the challenge anyway. She already knew Sue took some odd chances, so her past flashing was no surprise. I could only tell her what she was ready to hear about the library night. When her horror dropped to mere shock, I shared the barest details about the 'party of 5', Lynn and the duct tape experience.
While Lois digested her sister's exploits,  I contacted Joe and told him what I was doing and where this might lead. He too was shocked by Sue's daring, but also aroused. As I expected, he was very interested in watching Sue strip. From past observations, I knew he wanted much more than that and would be thrilled to share his 'frigid' wife with me to get Sue. He was about ready to give up on her. This weekend might also change Lois and save their marriage. "If there's any chance of this working, Lois has to participate or at least watch. You've already seen that she'll ignore or resist anything you suggest, so you'll have to leave all the directing to me and really hold back until I tell you to get involved. There will be times when that will be very hard, but Sue will help you. Her willingness must set the limits, or there's no trust. If this works OK, she'll come to convince you to come visit us. Play along." He agreed. "On a scale of 1 - 100, with 50 average, where do you see Lois on sex activity and openness to new ideas?"
"Since she's not open to anything, even quick missionary is a chore and she won't do oral- either way, so mayyybe 10. I know what's changed that's helping her to suddenly open her mind a little more. We don't talk much, but the word 'divorce' came up a few times."
When Lois called again, I suggested that she could lead Joe into changes by changing herself first. "If you're willing to try, I have some ideas that might help. But you have to be truly willing, very brave and daring. I'm sure you'll find many pleasant surprises and probably ease tensions between you and Joe. You'll have to be nakedly honest with me about many things, even very personal, very intimate, questions I'll have to ask you, and trust me for just a few weeks. If you don't answer honestly, I can't help you."
For the next two hours, I got information  about her marriage, sex history and attitudes, preferences etc. Most of it was old news, but I could tell she was struggling and being openly and bravely honest. She told me her first time sex at fourteen was forced, felt grimy and was very painful. Her limited experience since then had been merely to do what she had to do and she never enjoyed it. When she allowed her husband to mount her, she tolerated the simplest 'missionary' only and afterwards ran quickly to clean up. She didn't even like Joe seeing her nude.
Anal, touching or even looking at a butthole, was out of the question. She almost never did oral, and in the maybe four times in ten years that she did, she had to gargle immediately afterwards despite HAVING NEVER tasted semen. Touching a penis was too dirty, and she wouldn't allow Joe to eat her since it's 'so dirty down there.' When Joe kissed her, she'd wipe her mouth. Touching tongues was 'disgusting' and very rare. Her germ phobia drove her to throw out food Joe or anyone else touched; to open public doors with her elbows and to always used a tissue to turn knobs etc.
She said, since twelve, she masturbated 'often' - two or three times a month - and barely enjoyed it! When she did, she had to sterilize her fingers before and after. If she cooperates, she'll have a new appreciation for what 'often' is. She shamefully admitted that after constantly hearing how great vibrators were, via women's mags, she disguised herself and bought her first just a year ago. It too was sterilized before and after each use. The first two times she used it, she rubbed it over her jeans. The next two, directly ON her panties. It was a month before she pressed it against her bare mons and eventually against her clit and barely inside her. From her descriptions of her orgasms, it was obvious she had never truly had one. No wonder she hated sex. I felt so terrible for her; and, regardless if I got anything or not from it, hoped I could help free her.
Lois seemed to have just developed a new curiosity and titillation , so I tried pushing a little more. I told her about Sue's early exposures and some of my own bawdy experiences, good and bad. Since she didn't shut down and was still listening to tales of Sue's stripping at open windows etc., I asked, "Have you ever gone skinny dipping or been to a nude beach?" I knew the answers.
"Hell no. Why would I do that?"
It was time to turn the challenge back on her. "Think about anyone you would feel OK being naked with. Even a doctor or your sister is fine. Once you're comfortable with that thought, imagine you two go to a nude beach. You may feel very awkward for ten minutes, but then notice that the people there don't stare at your beautiful body for long. Just as you aren't turned off staring at them anymore. Notice the families there. Naked infants, toddlers, kids, teens, parents and grandparents, all comfortable. Many won't be as attractive as you are, so imagine how hard it may be for them to expose their fat or ugly bodies. If it helps, I'll go with you. Let me know how you make out with the exercise." I never expected to hear back from her again.
Shockingly, Lois called back to say, "I might skinny dip with my sister at an inside pool and if that went OK, then I might go with Joe.  I'm not sure about it at a lake or outside pool. The nude beach image was even harder. I couldn't ever go there with you, sorry."
"I'll remember you said that! You did great, Lois. I'm impressed. I wasn't sure you would try going this far. Now, are you willing to take a small dare and tackle a bigger exercise?" If she were not ready, I knew that we probably wouldn't talk for another year. I suggested, "go sunbathe for half an hour in your high fenced yard in the smallest bikini you have. BUT, after ten minutes, take off your top and leave it off for twenty more minutes. I don't need an answer since this exercise is strictly for your benefit and I won't be watching. My loss. Sleep on it."
Lois was so prudish and conservative, I figured there was no way she'd be so daring. She called me the NEXT afternoon and breathlessly shouted, "I did it!  I don't believe I actually did it! I changed in the bathroom, then just walking out in my very conservative bikini was daunting since I don't like anyone to see my very thin legs, or huge ugly top. The neighbors can't see over my fence, so I went out in just the two-piece swim suit. After a few minutes, I got very nervous and hyperventilated just thinking about taking off my top outside.
"Well, I hoped the sky wouldn't fall, then triple checked that I couldn't see neighbors and, while seated on the lounger, I reached back and ... opened my top. I held the front against me a minute then let it fall to my lap. I held my breath. Nothing happened, yet my breasts and bare nipples were in the bright sun! I did it! It was so odd watching my nipples pucker in the warm breeze. My heart was racing for the next twenty minutes until I put the top on and checked the neighbors again. I survived it! Nearly naked outside! What a rush! Should I do it again ?"
GOSH, she said 'nipple.' Something's up since she usually grimaced at 'damn' or 'bitch' and other such extreme language. "Congratulations. Of course you should. After just one or two more times I'm afraid it won't be so exciting. I'll guide you more when you're ready. You'll let me know and set the pace. I hope you noticed that you're already telling me things that were much too personal to even hint at last week. When you're up for it, your next challenge is to sunbathe bottomless outside."
"Yeah right! Totally nude outside? Why would I do that?"
"You don't have to. Remember, you must be willing and trust my guidance. Lois, know that I love you and won't push you too hard or let you get hurt. If you do that, you can do the exercises. Let me know. You should push yourself to start using less clinical terms too. I want you to be very descriptive about what you do. Use sexy, even lusty, descriptions and don't worry how it sounds to me. Enjoy the experience and reliving it." Two days passed with no contact. Then the phone rang with a nervous energy that charged the air.
Lois was hopping with excitement like a six-year-old at a cotton candy faire. "You were right! It wasn't hard to go topless after two days, though I was still nervous. OK, here goes. I'm not sure how sexy this will be, but I'll try.  After ten minutes being topless today, I bit my lip and began slowly sliding my blue bottoms down. I paused at my hairline, watched the raven hair lighten in the sun and listened for people. The silence was surreal! I pulled the suit lower and paused when my uhh ... mons was exposed. It looked so weird, pale, pristine even and very bright in the sunlight. It's never seen the sun! My full patch waved in the gentle breeze. 
"One more gulp, and I pulled the bottom down my legs. I noticed that my lips flexed open as I dragged it over each foot and off completely. Just to be more daring,  I tossed the towel, top and bottom into the house! I was scared! If anyone came by I couldn't cover up. Damn it was exciting! I trembled for a few minutes, then opened my legs slowly. I could already see my vulnerable vulva opening like a lover's mouth. My mind fought to keep my legs open a little. When nothing happened, I gently put my feet on the ground on either side of the lounger. That spread my legs wide and kept them open . My vagina was getting puffy, and watching it  begin to glisten in the light was oddly exciting. The warm breeze felt chilly blowing thru my open, um kitty. How's that!"
No need to correct her terminology. "Amazing! I never thought you'd get so far. In just six days you went from 'nobody sees my legs' to naked in your yard. Great progress! Have you been reading romance novels or what? And nobody was hurt, right? Ummm, I, uhh, have to go, but think about how you might push your limits just a little more and let me know. Bye"
There was a reason I had to go quickly. I imagined her exposing her pale big beautiful bouncy breasts slowly. I'd seen them before and they were impressive. Lois really is a beautiful petite woman. A little too thin for my taste, but offsetting her tiny ass and narrow hips on a 5'3" 99 lbs. body were her hip length jet black hair, bright blue glittering eyes, very pretty, thin and slightly oval face, firm full plumped-plate C cups with moderately sized dusty rose nipples, thin shapely legs and a killer smile. Yes, she got my juices going, but until now she was too distant to approach safely. The way she described peeling off her bottoms, if not sexy, was very vivid. So much that I pulled out my dick and choked it as she spoke. Sue knew what I was attempting with Lois, but wondered why I was wanking myself. She dropped to her knees and swallowed Pete in one big gulp, then pumped me gently. I didn't think Lois was ready yet to hear me moan.
Two more days passed, but Lois wasn't idle. She followed my next two suggestions and pushed her limits by changing into her bikini in the living room behind just shear drapes  and walked outside topless,  risking being seen over her fence. The next day, she undressed again behind the transparent drapes then walked into her yard naked.  She threw her arms up in a V and spun four times nude. She said she felt oddly liberated. That's when I decided I'd better keep track of how many FIRSTS she had since the eventual total may likely surprise us all. So far she had .
Could Lois be ready to watch Sue strip? I told her more of what Sue did with friends and at the library. She didn't (want to) believe it, but I heard a tinge of arousal. "The friend's expo party we'd planned for the next weekend is off and we'd like you to come up. Expect Sue to take advantage and let her expose herself to Joe and you if she wants to. You can see how much I adapted, and consider how you might have to adapt too if you're willing. Only come if you're ready to watch and maybe participate. I just don't want you to run off and fume in the car all day. You OK with that? Are you ready to absolutely trust me unconditionally and let me be your guide? You may have to convince Joe to come and participate."
"I don't think he'll have a problem. Let me sleep on it all and I'll let you know soon." 
With the weekend coming fast, Lois called the next day and said, "We're coming,  but don't expect too much. You have my commitment to trust your guidance. There's umm ... no one else I'd trust this way."