Chapter 02 - Cindy Gets Braver

Preface and disclaimers:

I wrote the 3rd story first with no plans to write more. But I like Cindy and decided to add more. It became obvious that I needed some background. As I wrote the background it took on a life of it's own now labeled parts 1 and 2. The voice is Cindy's. I edited minimally at her request. Ok? Part three is where I come in. I wrote it in my voice. Hopefully not too confusing...

This is work is copyrighted. It is published on Literotica.com. Protections apply. I like comments on my work. Critical ones are fine as long as they are constructive. I'm not expert at this game. Unfortunately, Literotica attracts trolls who get some sort of thrill by anonymously posting unconstructive and rude comments. Sad but true. The delete function eradicates them.

Usual disclaimers apply. This is pornography. If it is illegal for you to obtain or read then please do not. Also, I elected not to add elements of safe sex. I am a fan of safe sex. Characters in my stories do not contract diseases like real people do.

Lastly, like a lot of fiction, some of this is real and some is not. Readers are encouraged to enjoy guessing what is real and what is fantasy.

2 -- Prologue part 2: Cindy Gets Brave

Things had changed. I was 45 and feeling perpetually horny and Jim was loving it. We were having lots of playfully kinky fun in our bedroom. I was still telling Jim stories about his naughty slut wife. We both still got worked up thinking about the times I had been shared with Mack.

One of Jim's long standing fantasies involved me going braless. This was something I had only done in private. But it was time for me to get a bit braver. I was old enough to enjoy this stuff and not worry about what other people might think. There were still limits that Jim respected. I have large breasts and very prominent nipples. I was not going to go braless around town. That would just be embarrassing. Jim was never pushy, which made all this much more possible. I'm shy about my body and I can be very stubborn.

That fall we planned a weekend to go see the fall colors. Jim reserved a room at a rustic lodge about half a days drive from home. I thought I'd surprise Jim by being a bit naughty on the trip. I wasn't sure yet what might work but I admit that the ideas were turning me on.

Looking through the closet I didn't find anything that inspired me. So I headed out shopping. At the mall I found a turtleneck sweater that might work. It was soft and a bit fuzzy. It was very red. In the changing room I took off my top and then my bra. Looking at myself topless in the full length mirror I liked what I saw, certainly not perfect but sexy nonetheless. I have a bit of extra pouch around my middle. My breasts are too big. They sag a bit but not as much as other big breasts. My nipples stick out way to much when they get hard, so much that I have to avoid flimsy bras most of the time.

Going braless was simply not something I had ever done. I pulled the sweater over my head and immediately fell in love. It was a bit tight in the chest but loose around my middle. It was long in the sleeves and hem requiring that it be pushed up my arms a bit and around my waist. The fabric felt heavenly against my bare breasts. My nipples were plainly obvious poking out under the soft fabric. It was sensual. Needless to say I bought it. To complete the outfit and in keeping with my new attitude I found a some tight jeans that were a bit stretchy. They left nothing to the imagination when seen from behind. I also found a red thong, another first for me, that matched the sweater.

All of this was packed away hidden from Jim.

The night before I whispered to Jim asking him if he would like his wife to be his naughty slut for the weekend. The thought made his cock that much harder. Teasingly, I refused to give him any details. But I sure did get a good fucking that night and the next morning.

For the ride out I wore my normal loose fitting jeans and a sweatshirt. I did wear one of my thinner bras and my nipples were slightly visible. Jim had a hard time driving as I kept touching them to make them hard every now and then. We were both enjoying the prolonged teasing. We arrived in time for dinner. Jim wanted a quicky but I told him I would take care of him later. I sent him down to get a table telling him I needed to use the bathroom, that I'd be along in a minute. I spent that minute changing into my new outfit. I took my long brown hair out of the pony tail and let it cascade down my back. My heart was pounding as I walked out of the room knowing that everyone that looked would see my braless breasts and protruding nipples. With the soft fabric gently rubbing my breasts and the thong snug against my pussy, I was in heat. I felt like I could cum any moment. My outfit might not seem outrageous to some men and women, but it was a big leap for me.

There was a younger guy in the elevator who blushed when I caught him looking at my nipples. Jim nearly fell off his chair when I walked into the dinning room. I tried to act casual. Inside I was boiling. My nipples started out stiff and stayed stiff. I could feel my pussy getting wet to the point that I was afraid I might have a wet spot showing through my jeans. I can't remember what I ate. Jim doesn't remember either. At one point I whispered to Jim that if I moved I was afraid the fabric stimulating my nipples would make me cum. We skipped desert.

Alone in the elevator, Jim gently took a hold of my nipples through the sweater. Neither of us said a thing as he softly rolled them through the fabric. I was so worked up that I nearly collapsed on the spot. Jim could barely walk due to his raging hard on. Back in the room Jim wanted to strip me and fuck me right a way but I had other plans. I made him take off all his clothes and lay in the middle of the bed, turning my back a shimmied out of my jeans giving Jim a look at me new, red thong. Then, still wearing the sweater, I proceeded to rub my breasts all over Jim. I think he was in heaven. I teased his face with my tits and ended with his cock nestled in my soft, fuzzy cleavage. I didn't want his cum all over my new sweater so I moved down little farther. Pulling the turtleneck up and the sleeves over my hands I started to massage his cock and balls with the sweater. I was rubbing the tip of his cock against my face and the neck of the sweater at the same time. I was doing all this very slowly trying my best to prevent him from cumming. When I figured he couldn't take it any more I started rubbing him faster. Only the tip of his cock was exposed. So I took it in my mouth and began to swirl my tongue over the sensitive head. With that his back arched and jets of cum filled my mouth. I managed to swallow it all, keeping the sweater clean.

After catching his breath Jim told me it was my turn. He had purchased some sweet almond oil. He had me lay back completely naked and proceeded to use the oil to massage my front. He paid lots of attention to me hyper sensitive breasts, He did my legs and thighs. Teasingly he touched just about everything except my clit. After all the stimulation of dinner and making Jim cum in my mouth, I was complete jello. He finally bent down and started to run his tongue over my clit. I was cumming within moments. It was one long, intense orgasm, prolonged by Jim gently licking the tip of my clit and fingering my G-spot. As my orgasm subsided he was on me and in me, fucking me with deep strokes that sent me back over the edge. As I came back to earth for the second time, Jim pulled out and slid his cock between my oiled breasts. I pushed them together and licked the tip of his cock whenever it came within range. The sweet almond oil didn't taste bad at all.. I loved the feeling of his hard cock sliding through my oily cleavage. I find it intensely erotic. And then he was cumming. He left a pool of cum between my breasts which I rubbed in along with the oil.

Saturday was a beautiful, sunny fall day. Jim had his willing slut before breakfast and again after. We then decided to go for a short hike on one of the nature trails near the lodge. To Jim's delight I put the sweater back on along with regular jeans and a light jacket. After a short while the jacket came off revealing the soft red sweater and my obviously braless breasts to anyone that might happen along. The first to come along was a couple about our age. The husband tried hard not to stare openly. At the same time his wife was pulling him along. We had to stop and laugh as soon as they were out of sight. We had a kiss and a grope as well, standing by a sun dappled rock. Then another couple came along. They stopped to say hi. Unlike the previous couple, they both seemed to like my sweater. The wife complimented me on it as she touched my arm to feel the softness. All the while, her husband tried hard not to stare openly at my rigid nipples. I smiled at the woman and told her the fabric felt delightful against my skin. I don't think there was any doubt in her mind that I found it erotic as well.

As we walked on I was beginning to fear that Jim might attack me right in the middle of trail. Rather than risk getting arrested we started looking for a bit of privacy somewhere off the trail. Scrambling carefully through the brush we found a large flat rock drenched in sun. There didn't seem to be any risk of being seen or surprised. It was perfect. Jim sat back as I opened his jeans and freed his hard cock. Once again I pulled the sleeves of the sweater down over my hands and proceeded to masturbate him. I took my time eventually ending with his cock in my mouth, followed by a very satisfied husband.

Back at the lodge Jim decided to take a nap. I headed down to the great room to enjoy the view of the mountains. After a while a young man sat in the recliner next to me. I realized he was the same one that had blushed charmingly in the elevator the day before. We exchanged a few pleasantries and he brought us both drinks from the bar. He was a very nice guy. I sat back and turned a bit toward him as we talked. I wanted to be sure he had a clear view of my soft sweater where it stretched over my full breasts. Dan was about 30 and in good shape. He and his brother Mark were up here to do some climbing.

Half way through the drinks he told me that he had to say something and that he hoped I would not be offended. I said no worries. He proceeded to compliment me on my sweater and the confidence that I exuded by going braless. He also told me he regretted that his girlfriend back home would never go braless. I blushed and thanked him. I told him that I was flattered and that I did not feel all that confident. He went on to say that I was very sensuous and that the confidence, real or not, only added to the picture. Blushing he mentioned that he and his brother had seen me on the trail earlier that day while my husband and I had been, err, relaxing on the rock. Before I could say anything he told me that they had both thought what they saw was very beautiful and erotic. My nipples were making it impossible to hide my arousal, a fact that Dan did not fail to miss.

This young man was doing wonders for my confidence. I mentioned that it was no problem, that in fact I rather enjoyed knowing that they had liked what they saw. Mustering some bravery, I asked Dan if I might stop by his room in a few minutes. Smiling, he gave me his room number. That gave me just enough time to explain to Jim that his wife was being a very naughty slut and that she would be back soon.

Here I was, chunky 45 year old slut in a braless sweater that had men drooling, knocking on the door of a young man that I had just met. Maybe I should have expected it but I was surprised to find two young men in the room, Dan and Mark, both in their undies, both muscular, both hard. I took off my shoes and socks, jeans and panties, all without a word. They both agreed that I should leave the sweater on.

It was quick and it was naughty. They laid me across the bed. Immediately I had a cock in my mouth and a tongue on my clit and four hands playing with my breasts through the sweater. I came hard while sucking a cock. Wow that was intense. Then I was on my hands and knees. I had a cock in each end. I was doing my best to suck the cock in my mouth and use my pussy muscles to massage the one in my cunt. But the truth is I was simply being fucked mercilessly from both ends with my braless tits swaying and my nipples rubbing against the soft sweater. I started to cum again and that set both boys off as well. The feeling of cum spurting into my mouth and pussy at the same time as I orgasmed uncontrollably was indescribable.

I was back in my room, weak kneed, barely 20 minutes after leaving. Jim was lying on his back stroking his cock. Without a word I stripped off my shoes and jeans and panties again. Crawling over Jim I settled down taking his cock deep in my sopping pussy. Handing him my panties I asked if he could feel the load of cum inside me. The silky feeling of being fucked with a fresh load of cum in my pussy is hard to describe, but it sure does feel amazing. Neither of us was moving but I could feel his cock get that much stiffer. I started to slide slowly up and down on his cock. Taking my panties back from him I pushed the cum covered crotch into my mouth. Realizing what a slut I was being was just too much. I started cumming and I kept cumming as Jim pulled on my nipples. I don't think I actually passed out but I don't really remember Jim's orgasm. He said it was amazing.

Later, after a nap and a shower I told Jim a bit about what had happened as he fucked his willing slut in the missionary position. He loved it and it was clear that we had enough new stories to keep Jim happy for months. Afterwards I had to tell Jim how amazing he is for letting me be naughty and enjoying it along with me.

The next morning it was time to leave. Jim and I had barely left the room during the previous 18 hours. I don't think he has ever cum that many times in so short a period. I was doing any naughty thing he could think of. I worshipped his cock and took it in every possible way. And while he was in me I would picture myself being naughty and I would cum. We were exhausted.

The sweater had to go back in the suitcase, after the hike and all the sex it was just not fit for the public. As a compromise I wore Jim's college sweatshirt without a bra. It was a bit tight and it was way naughtier than normal for me. We ran into Dan and Mark in the parking lot. Jim smiled and waved as I bounced over and kissed them both. The kisses were not the sisterly type and I didn't care who saw me at that point. They were French kisses with my braless tits pressed firmly against each boy. I think I slept all the way home.