No to Pasties, Yes to the Tits

Ours is a monogamous and happy marriage of over 20 years. Throughout the years, she has done lots of crazy/naughty/erotic stuff to make me happy. I've no complaints. Periodically I will still nudge her to try something new that tests her limits. About two months I nudged her again.

It all started with an assignment in one of her college classes. She was to do something that violated a social norm, monitor the reactions of those present (and herself), and write a report. After she made a few suggestions, I chimed in with "how about going topless in front of a stranger?"

I was shot down right away when she was lukewarm about the idea. After a while, she said she would still consider it. With the hope of getting her to do something similar I suggested, "How about if you are wearing pasties?"

She seemed a little more receptive to this idea so I ran with it. Without her knowing, I bought some pasties at Target and presented them too her. She had never worn them before, but put them to use the next day. Most days she is braless. With certain tops, and when it's cold, her nipples are quite pronounced. The pasties have made it possible for her to be braless with all her outfits and all the time.

She eventually settled on a completely unrelated idea for her class project. This was a disappointment for me. Without her knowing, I had posted an ad on Craigslist to find volunteers. I had gone so far as to arrange a day and location with two different guys (one was a back-up). I added a third later. Through emails, I made sure we didn't live in the same community, work for the same company etc. I wished for my wife and I to remain anonymous.

My plan was to meet on a weekday at a picnic area about an hour from home. We would sit at a table and make small talk. Throughout the conversation, and if she remained comfortable with the situation, she would unbutton her top revealing more breast. Eventually she would have the top completely undone or removed. I, of course, would be recording 'scientific' observations during the entire process. When she decided to do the other idea. I sent out the rejection emails to the fellas and thought that was the end of it.

Not too much later, she had a week-long break in school. We made the most of it and went to a "B and B" for a romantic overnight of massages, fine dining, soaking in the hot tub, and, hopefully, some hot sex. We got there a little early for check-in, so we went for a short drive to catch some scenery and just talk. Soon we found ourselves talking about her class project.

I asked, "You remember that class project you had where I had suggested you go topless, or at least have some pasties on, in front of a stranger?"

How could she not remember? She wondered aloud "Yeah. You bought me the pasties and seemed quite excited about the idea of me wearing them for some guy. Are you still thinking about it?".

Obviously, I had. I probably should not have brought it up, but now I was committed to saying something. I waded in by saying, "As a matter of fact I have. I know the class project is over, but I would still like to do it someday."

I fully expected to be rebuffed. Surprisingly, she wasn't at all irritated or angry. Actually, she seemed curious when she asked "Who would that be? Someone you know? If I were to ever do such a thing it would have to be a total stranger."

I agreed that it would have to be a stranger. I suggested, "I can place an ad on Craigslist. I guarantee we can find somebody."

She answered "I doubt someone would willing to go through all that trouble just to see my pastie-covered boobs for just a couple of minutes? Especially if they knew how old I am and what I look like. I wouldn't want somebody showing up then turning right around and leaving."

She is in her mid-40's and could be accurately described as a 'BBW'. The emphasis being the 'beautiful. I explained, "I want to have you do the boob flashing, but more importantly the teasing leading up to it. First, I get the thrill of seeing you flash someone. Second, you get proof that other guys, besides me, find you sexy."

She thought about my statement while I kept driving. After a few minutes, she unloaded her thoughts on the matter saying "First, slowing stripping while talking just sounds kind of creepy. If I were to do it, I would talk to them for a while...get acquainted... and make sure they knew what might happen. Assuming things proceed according to plan, I would just take the top off, talk for a few more minutes, then be done with it"

Anything that had her getting topless in front of a stranger, would be fine by me. After a few seconds, she continued "I still don't think I could go through with it, even wearing pasties. If I were a safe distance from him, and arranged an 'accidental' flash of my tits, I would be okay with that."

I asked, "How is it more uncomfortable if a guy sees your boobs close-up, but covered by pasties, versus completely exposed at a distance?"

She paused a moment before answering "It isn't a big deal whether he sees my nipples. It's the conversing with him that makes me cringe. If he is close, and especially if I am talking to him, they become very real. If he is at a distance, and we aren't talking, then there is a sense of detachment. If I were to do something like that I would need to feel detached from the situation."

I countered, "That makes no sense to me, but I believe you. It just seems kind of weird."

She continued "Not seeing the person would probably help a whole lot too. Think about the times when I have been topless or naked outdoors during the day. I picked the timing and place. Someone could potentially see me but only at a distance. Even If they stopped and paid attention, all they would have seen was a naked woman, but they wouldn't see 'me'. You probably weren't paying attention, but when I was doing things, I was never looking towards where the potential onlookers. That was I could just pretend nobody was there. Does that make sense?"

I thought about these past instances and answered "Sort of."

I asked, "So, if you are anonymous and the guy is out of sight out of mind, so that it is 'just you and me' then you are okay with doing something?"

"Yeah" was her answer.

I was stunned at this revelation. I didn't know what I should say or do next. She got things rolling by asking, "Are you getting any ideas in that dirty little mind of yours?"

"As a matter of fact, I am" was my answer.

"Would you be okay if we went to a picnic area and met a guy there. You could be blindfolded, and not speak. They would speak minimally, quietly, and only to me. I could take your top off and let them see your tits. And you'd be okay with that?"

She paused before answering "Sure."

Now I started in with a series of follow-up questions. "What about this, what about that etc." for which she gave me more answers.

After this game of twenty questions I had her agreeing in principal to potentially doing a lot of naughty stuff in front of a stranger. When I suggested that I make arrangements when I get home, she seemed suddenly reluctant.

I asked, "What's wrong?"

She answered, "I told you earlier, nobody is going to want to see me topless, much less naked."

Yes, she was out of the age range for a lot of guys, but I reminded her that guys our age still like women our age. I assured her that I would get the right guy. I told her again that she was beautiful and sexy. She smiled and seemed quite pleased. Still, I had not addressed her weight.

I told her, "Most guys like their women 'soft' and not 'hard'. We also like them with curves. I absolutely promise that we will find lots of guys that will love the way you look."

She seemed doubtful as she told me, "Well, I guess I will need to trust you to find a suitable candidate. I don't want to know about them. I don't want to see them. I don't even want to see their picture. And they can't know anything about either of us. They have to be strangers and stay that way."

I was nodding all along because I was in absolute agreement.

We didn't talk about this topic for the rest of that trip or a few days afterwards. Perhaps she thought I would forgot about it, but I started making plans as soon as I got home. That night in the hotel, I got her blindfolded in front of a full-length mirror in our room. I slowly undressed her, being careful to remember what looked hot. Instead of simply getting her topless for a stranger, I was possible to do a whole lot more.

I had arranged for us to have another overnight getaway with the intent of exposing her to a stranger. I let her know that my plan was in place about two days beforehand. She said, "I kind of figured this was coming." She seemed rather matter-of-fact about it all.

It was interesting when I sent out a new round of emails to the guys that I had just called things off with. The emails essentially went, 'You remember how I was trying to get my wife to show you her pastie-covered tits? And she backed out? Well, now she is willing to get completely naked in front of you.'

If it were me getting the email, I would have thought it was complete bullshit! All of them expressed surprise, but none of them thought I was lying.

One of them asked if there was any chance he could watch us having sex. It was a long-standing fantasy of his. That put a new wrinkle on things. It was all about seeing her naked in front of another guy. I had not considered the prospect of me being that way, and aroused at that. All of them wanted to know if they could pleasure themselves while watching. I had the sense that I was getting in over my head and had to clarify the limits, but first I had to talk to my wife.

I told her the guys wanted to masturbate while watching her. Her answer floored me. "Well, I just assumed that they would be. It would be weird if they didn't. Just make sure they do it quietly and after they are done, they leave."

I then mentioned the suggestion that we have sex while they watched. Again, her answer left me stunned, "That would be fine. I just want don't want any 'gyno' shots."

Even though I had already groomed three candidates, I decided to start a new ad on Craigslist that said what I had in mind, including the limits. They would sit on their chair and observe, there would be no contact. Comments and questions would be directed to me only. We would start stripping her out of her dress and see where things went. Nothing was guaranteed. If my wife or I pulled the plug, the guy had to leave.

All the responders apparently didn't read the entire post. I was getting dick pictures, and they all assumed they were going to fuck my wife. Nobody new really came out of it, so I would be sticking with the original three guys. All of them agreed to the conditions and recommitted to being available that Friday.

Now was the time to tell her. I spelled out what I had done. The ad, the back and forth emails to make sure we didn't have some freaks, the conditions, the time and place. She just answered, "Cool" and went about her business.

Until that Friday finally rolled around, her getting naked in front of a stranger was all I could think of. I started scripting the whole thing in my head, but once I got her naked, I was drawing a blank. I still didn't know if I could go through with making love to her with somebody watching.

Things started to unravel about an hour before we left. My first choice suddenly couldn't get away from work that evening. 'No worries' I thought. My second choice was already staying at the resort where we were going. Months earlier he found out he had to attend a conference there. What was the chance of that happening? I figured it was meant to be! When we got to the hotel, I started emailing him to confirm that he was on for that evening. I got no answer. I was starting to panic. I had made this huge erotic breakthrough with my wife and now nobody was going to make it. I was pissed because not only was I going to be bummed out, but she was probably going to have her suspicions confirmed that she wasn't sexy or desirable. I emailed my third choice and asked if he could be there in two hours. He responded back right away, "no problem...be there at seven."

She saw me furiously typing away on the laptop and asked, "Is everything okay?"

I just smiled and said, "Yup."

I turned to her and asked, "Are you nervous or scared?"

"Not really scared, just nervous. I might need something to quiet my nerves" she answered.

We could hang around until it was time to get ready, maybe hit the steam room or hot tub, followed by dinner. We had early reservations so our meal could be leisurely, but we would stay on schedule. I didn't want to be late to meeting our guest at the appointed place.

When we finally began showering and getting ready the whole situation became quite real for me. I still couldn't believe it was going to happen. I have alluded to lots of naughty stuff she has done over the years, but this was probably the most erotic and limit-pushing thing she had attempted. As we got dressed I reminded her that she could pull the plug any time she wanted.

As she was doing her make-up she explained, "This is really important for you so I will take it as far as I can honey. You've made a lot of arrangements and I would hate to disappoint you...or our guest." She said with a smirk.

I reviewed the rules and limits with her one final time. She must have sensed my own hesitance because she asked, "Are you going to be okay fucking me in front of him?"

I honestly answered, "I don't know. Maybe we'll find out."

We finished getting dressed and left for dinner. The restaurant was empty when we got there. I guess we didn't really need reservations. After ordering, I scanned the entire place to make sure we were alone. There were no other diners and the wait staff was still sparse.

She was wearing a little black dress that I had selected for her about a month earlier. It had a wrap-around neck line that made getting peeks of her right boob a possibility. Too bad for me I was sitting on the wrong side. I reached across and put my hands under the fabric. I started caressing the tops of her tits. She did nothing but smile. After about fifteen seconds, I pulled the fabric aside to expose her right tit and tweaked her nipple. Our waiter suddenly emerged from the kitchen bearing drinks and appetizers. I quickly put her boob back in and brought my hand back to my side of the table. Her back was facing the kitchen so the waiter couldn't have seen anything aside from me rapidly moving my hand back from the front of her dress. I suppose he could have made a good guess what I was doing. When he got to our table, he was overtly friendly and attentive while he arranged things. Obviously, he knew I had been copping a feel and had no problem with it.

When he went back into the kitchen, I commented on his increased attention to detail. My wife pointed to the large glass windows we were facing and explained, "I have been watching myself in the glass since I sat down. The sun is getting lower, we are starting to get some shadows on the glass and the light is more indirect..."

I mumbled a quick "Uh huh."

"Well, the combination of light outside and the light in here coupled with me wearing a black dress that contrasts my skin...." She paused with the hope I would get it figure it out, but I didn't.

"You might as well have pulled my tit out in front of a mirror! He saw everything."

We chuckled a little bit, and I promised to behave for the rest of the meal. I didn't want to jeopardize the main event. I told her, "the waiter obviously likes bigger girls".

At this point I think was starting to believe that she was going to be a hit tonight. The service was impeccable the rest of the meal. After dessert, we were ahead of schedule. We had plenty of time to get back to our room. She could make her preparations while I went back out to meet our guest (who I will refer to as 'Jim'.) Unfortunately, her nerves were finally starting to get the best of her at the end of the meal. She said it all seemed like an uncertain future thing until right then. She ordered a cocktail and began to slowly sip it. When she finally finished, we were now behind schedule. Was she still going to go through with it?

We quickly paid then headed down to the room. The plan was for me to meet our guest (I'll call him Jim) and talk to him for a few minutes as a final check that he wasn't a weirdo. Then I would review the rules and limits with him a final time before heading up to the room. She went to the room, I went to meet Jim.

I arrived at the rendezvous point about five minutes late. I saw a guy heading into the elevator as I rounded the corner. Nobody was there. All the preparations were for nothing. I sat there a minute wondering what I was going to say to my wife. Just then the elevators opened. The guy I saw earlier stepped out. It was Jim.

He said, "I was going to leave, but I thought you might have been the guy I was supposed to meet, so I decided to come back up to make sure."

I answered, "I am definitely the guy you are looking for. Thanks for coming back up Jim."

We sat down and talked things over. I reviewed the rules and limits. He just gently nodded in affirmation all the while. He looked and spoke like a normal guy. As we started to head up to the room I asked him, "What the craziest thing like this you've ever done?"

His answer was swift, "a threesome with a buddy and his girlfriend."

I said, "Cool. When and where?"

He answered while motioning downstairs, "Right here, about two months back."

That kind of blind-sided me for no good reason. I reminded Jim that it wasn't going to get anywhere near as crazy as a threesome tonight. I also reminded him that my wife was a big girl and that he needed to compliment her periodically. He was still cool with everything. I pulled out my phone and texted her to say we would be up in two minutes.

I opened the door and looked inside to make sure that she was ready for me and Jim. She was wearing the outfit we had dinner in, sitting on the edge of the bed, and blindfolded. She was ready, so we came in. I had already arranged a chair and coffee table as Jim's 'viewing' area. She had laid out a bottled water, a wash-cloth, and a tube of lotion. Obviously, she remembered that Jim would be doing more than just watching. I showed Jim his place, and waited for him to get situated. Then I walked over to her, took her by the hand and helped her up. I guided her to a spot at the foot of the bed which was about six feet away from Jim. It was just enough distance to ensure that contact would be prevented.

I whispered into her ear, "Ready?" to which she nodded in affirmation.

"Then let's begin" I again whispered.

"She is lovely isn't she Jim?"

He answered, "Yes she is."

I thought it would be better if she didn't have jewelry on. That way her earrings and necklaces won't catch on something and hurt her. She insisted on wearing a necklace and matching earrings. Pointing to them I said, "She wanted to be even more beautiful for you Jim, so she wore these."

"Tell her thanks", he answered.

I whispered into her ear, "Still okay?" to which she nodded.

I put my fingers on her shoulders and moved slowly down the outer surface of her arms. Like most women, my wife enjoys a soft touch. Her response confirmed it. She smiled slightly as she let out a tiny moan periodically. I suddenly remembered that I had bought some cotton gloves for tonight. At the risk of interrupting a wonderful start I said, "One second" as I went to the drawer and retrieved the gloves.

I put them on and started over with the gloves on. I whispered, "Better? Or do you want just the fingers?" into her ear.

She answered with a surprisingly enthusiastic "uh-huh".