My MILF Won the Wet T-shirt Contest

My heart raced and I did a double take at one of the images I was perusing on a website. My job required a fair amount of travel, and it wasn't uncommon for me to relax in my hotel room late at night and peruse some websites feasting on various images of attractive members of the opposite sex. I wasn't a big fan of the real hardcore stuff but rather preferred what my generation referred to as T & A. For me an attractive woman, preferably a girl next door type, in various sexy outfits or lingerie or stripping down in a teasing fashion was a pleasant way to relax before turning in.

I grabbed my reading glasses and looked closer at the image. I clicked on it to enlarge it. I studied the picture in detail and three others in the set. The woman was an attractive middle-aged woman, long brown hair, a very nice figure, wearing very sexy outfits and a different top in each photo. She was in a backyard patio deck area and based on the shadows and light levels it was near sunset. Interestingly, the woman's face was mostly blurred out in the photos, but she appeared to be smiling. The resolution wasn't very high suggesting they had been taken with a telephoto lens at some distance. But the pictures were clear enough to show that the woman's tops were soaked and shear and clingy enough to reveal aroused nipples, brown areola, and shapely full breasts. One image showed a white top being sprayed with a stream of water.

The woman was my wife.

It took me a few moments for the reality to soak in as the events depicted had occurred about eight years earlier. But I hadn't taken the pictures or submitted them to a website. Their appearance had me puzzled and concerned.

I noticed all four photos had been submitted by someone with the screen name of Johnnyboy. The pictures had been on the site about two years. They were tightly cropped and showed no background. Each photo had been viewed thousands of times and they all had hundreds of "Likes". There were also hundreds of comments - the vast majority begging for more pictures, several asking who the MILF was and numerous expressing their desires to perform various acts with the woman in the pictures.

I opened my laptop and logged onto the site so that I could enlarge the pictures on the bigger screen. I was looking for any evidence that might explain by whom and how the photos were taken. They appeared to have been taken from our neighbors' house to the north of us. I couldn't imagine the older widow living there being party to voyeuristic pictures when I remembered that she had only lived there six years and had been preceded by a woman and her teenage son, Johnny. It was starting to make sense that the teenage neighbor boy, seemingly equipped with a telephoto lens camera had been spying on my wife and I that night. His second-floor bedroom window might have been a near perfect vantage point.

As I recalled he now lived halfway across the country and was most probably in his early 20s when he posted the photos. His discretion in cropping the photos and blurring Monica's face had me somewhat perplexed until I recalled how helpful Monica had been to him and his mother when his father passed. Monica had comforted them both and tutored him through junior high math as he struggled with adjusting to the loss of his father. I could imagine him not wanting to do anything to hurt Monica. But I also wondered how many other pictures he had, if he had any of Monica flashing her breasts or others that were more revealing than those he posted.

I recalled his mother's name and searched social media. It took about 45 minutes of sorting but I finally found her, now a resident of Ohio. Her son who was now a handsome young man was a junior at Ohio State studying accounting - I guess he learned his math. I found his social media page and sent a friend request. I closed my laptop for the night and laid back reflecting on that night some eight years earlier.

I smiled as I recalled the evening.

It was a Saturday night in August. The kids were at summer camp and Monica, my wife and I had 10 days alone. On Friday night we'd been out to dinner with a group of two other couples and as the evening progressed and the drinks flowed one of the other wives admitted to having been in a wet T shirt contest years earlier when she was in college. My wife quickly noted that she was both too bashful and too flat chested to participate in those events while at college twenty years earlier. The rest of the evening was spent sharing various outrageous stories about college days - most often recounting events that had been observed not necessarily participated in.

On our way home that evening I mentioned to Monica that her figure was certainly competitive for wet T shirt contest now. She thanked me for the compliment and acknowledged that two kids and 20 pounds had left her with a considerably shapelier figure than she had during her college days. She had transitioned from something akin to the typical figure of a ballet dancer to one that might very accurately be described as a MILF. She had gone from a 34A to a 36C bust and added three inches to her hips resulting in a 36-26-36 figure at age 42.

That Saturday morning, I mentioned to Monica that I was planning to grill steaks by the hot tub for dinner that evening and that after dinner I wanted her to participate in a wet T shirt contest. She looked at me as if I were nuts and presumed I was kidding. I reiterated, "No, I'm serious and you're going to win the contest as well."

We went about our Saturday routine the rest of the day and not much was said except for me mentioning on a couple of occasions how I was excited about the wet T shirt contest. Monica reacted by laughing about my joking. I only had a few things to do to prep for the evening's festivities. I had to make a pitcher of strong, inhibition lowering margaritas and discreetly dig through Monica's lingerie drawer and closet in search of an assortment of outfits for Monica to wear in the Wet T shirt contest I had planned.

After steak, salad, and I plying Monica with a second large Margarita I told her it was time for the wet T shirt contest. I continued, "You're guaranteed to be winner since you're the only contestant and I am the only judge, but you have to model four different outfits I've picked out for you. I need to strut your stuff and pose while I wet you down. We will see which top works best then you can use that in a real competition someday."

Monica giggled and accused me of being crazy and perverted. I responded, "I plead guilty, now go get your cute ass to the bedroom and put on one of the outfits I have laid out for you."

Monica quickly drained her Margarita and said, "You've got to be kidding, I don't believe you."

Then she stood and walked to the house to check the bedroom. If I was a betting man, I would have bet about ten to one odds that Monica would not follow through when she saw what I had laid out for her. The hot tub was turned on and warmed up and the hose and a pile of towels was handy in case she returned. When she didn't immediately return to protest, I knew she was either quite upset or perhaps, fingers crossed, actually putting on one of the outfits.

It seemed like forever but was probably only 10 minutes. Monica returns wearing a silky light pink top and matching tap pants. I was impressed that she had put on a pair of heels as well. Her only response was, "If you expect me to go through with this, I need another drink."

As I poured another drink, I told her she looked great and could choose between hose or hot tub for this outfit. I turned on the outdoor speaker system with some dance music that I had previously selected and pretended to be the master of ceremonies announcing, "Tonight's first contestant is Monica sporting a pink camisole and tap pant nightie set. She's an accountant and mother who's making up for experiences she missed in college. Welcome Monica to her first ever wet T shirt contest."

As I clapped Monica was giggling but starting to move to the music and made her way toward the hot tub. She had that "I can't believe I'm actually doing this." look on her face as she swayed and swirled moving toward the hot tub. She stepped out of her heels and stepped into the hot tub, the first step putting her in knee deep water. "You better appreciate this, and don't you dare laugh." she threatened as she stepped to the bottom of the hot tub soaking her tap pants and standing in now waist deep water. She swayed back and forth in the water dipping slightly deeper several times allowing the water to soak more of the camisole leaving the fabric clinging to her midriff and turning more shear. As the water line reached the bottom of her breasts, she used her hands to splash small amounts of water on her cleavage. The effective tease had me impressed and aroused. The routine continued for about 5 more minutes as she completely dunked her top several times, shook her chest and climbed from the hot tub to show off her clinging sheer outfit.

I clapped my applause and using my master of ceremonies voice congratulated Monica on her performance noting that she set a high bar for the remaining contestants. Monica patted herself with a towel, took another gulp of her drink, grabbed her high heels and headed toward the house.

About 10 minutes later Monica reappeared. This time she was wearing a set of lingerie I had laid out for her. White panties with a satin front and shear back, a white corset from the back of her closet. It was the corset she had worn with her wedding dress. The front panels were shear between the boning and the bra was a three-quarter cup lacy under wire configuration. Even though I had removed the pushup pads, Monica's now much larger bust spilled over the tops of the cups in an enticing manner. Garter straps hung from the bottom of the corset and were attached to a pair of white silky stockings. The black heels completed the outfit.

I motioned Monica to move toward the railing on the deck and reached for the hose. I adjusted the water to a substantial but not overpowering flow. As Monica sipped her drink, she noted the corset hadn't seen the light of day since our wedding night. She smiled as she noted it still fit though she could no longer use the tightest hooks when she fastened it and the cup size was too small to wear for any length of time.

She swirled around and made some dance steps wiggling her hips and shaking her bust. While it was clear she was an amateur she seemed to be enjoying herself. Shifting to my master of ceremonies role, "Miss Trousseau is our second contestant this evening and she has been kind enough to share with us an outfit that had previously been restricted to a single viewer."

I approached with the hose stream first splashing her stockings and shoes then moving up to wet her panties with the cool water. I instructed her to turn around and soaked the back, now shear panties. She squealed as the cool water soaked her. The panels covering her midriff next yielded to the hose. Finally, the stream of water cascaded over her cleavage and soaked her lacy bra cups. Miss Trousseau blushed as her aroused nipples made themselves very visible through the thin bra cups. She smiled and shimmied, even rubbed her hands over her breasts then leaned forward to showcase her breasts bulging from the soaked cups for the audience of one to enjoy.

Another towel, another gulp of her drink and she was off to the house for her third outfit. I was somewhat curious to see if she would be willing to wear it and get it soaked as it was a thin white silk blouse meant to be worn with a camisole and a black pencil skirt that she wore for evening business meetings. Black seamed stay-up stockings completed the outfit.

Monica returned and pirouetted on the deck displaying her outfit. She had added hot pink lipstick and additional makeup giving her a sultry but sophisticated look. She sipped on her drink but managed to spill some on her blouse. She responded as she walked toward the hot tub, "Opps, I guess I'll have to wash that off."

She looked beautiful. She sat on the edge of the tub and climbed in purring about how nice the warm water felt. The black shoes, stockings, and skirt submerged into the bubbling water. Without pausing she slipped deeper completely soaking her blouse. She relaxed in the warm bubbly water and giggled as the air bubbles puffed up her blouse. She asked me to refill her drink. She had already finished nearly three margaritas, a record for her but she was still very nimble if somewhat giggly. Since we were off tomorrow, I figured she could sleep off the effects Sunday morning.

And she emerged from the hot tub her black, skintight dripping wet skirt hugged her shapely figure. No panty lines. Her white silky blouse similarly clung to her body leaving nothing to the imagination as the blouse was virtually transparent even in the late evening light. Her engorged nipples and puffy areolas were on full display as she posed on the deck. "I hope you're enjoying this." She said as she again took a sip of her drink and grab for a towel before heading for the house.

About 10 minutes later Monica reemerged from the house this time wearing the last outfit I had laid out for her. It was a pair of short shorts and a white, thin cotton tank top only long enough to extend slightly below her breasts. It was an outfit more typical of what you might see in a college wet T shirt contest. Stepping into my master of ceremonies roll, I announced that our last contestant of the evening was Candy. I noted several beautiful contestants had competed before her and she'd really have to put on quite a show to impress the judges.

Candy smiled, took a final drink, put her glass down, turned up the music, and picked up the hose. She spent the next few moments dancing as if the hose was her partner pulling it between her legs, between her breasts, and around her waist. She said, "I know the competition has been hot." as she stuck the hose nozzle down her shorts and squeezed the trigger moaning as the cold water flooded her panties.

I had never seen Monica this expressive as her eyes rolled and she moaned "Yes" as the cold water flowed out of her shorts and down her legs. She turned and repeated the actions down the back of her shorts while continuing to sway to the music.

I was clapping aggressively as my rock-hard cock stretched down my pant leg. Candy smiled as she pulled the hose from her shorts and soaked her top. The flimsy top did little too constrained her bouncing breasts as she dance to the music shaking her body. The top clung tightly doing little to conceal her breasts and aroused nipples.

As she danced, I shouted, "Lose those shorts." She mocked being surprised and spoke. "But I only have a white thong on."

Returning to my master of ceremonies voice I told Candy that the crowd wanted her to lose the shorts to earn their votes as the contest winner.

She giggled as she unsnapped her shorts pulled down the zipper and shimmied out of the wet shorts carefully so as not to pull down her panties. I was rewarded with the sight of a clinging pair of white panties that did little to hide her pubic hair landing strip and nothing to hide her ass cheeks framed by the thong panties.

As I clapped and laughed, I told Candy the crowd wanted to see a little titty flash before the final vote. Monica was still sober enough to ask what the first-place prize was for the winner.

I laughed and said, "The winner gets a romp in the sack with the judge and a chance to sleep in as long as she wants in the morning and a promise for dinner at any restaurant you choose."

Monica giggled then slowly lifted her top shaking her breasts to the cheers of the crowd.

Needless to say the winner collected on her romp with the judge prize that night as it took about two hours for the judge to finish delivering her prize.

After my mind replayed that very pleasant night, I turned my attention two other issues: should I tell Monica? If Johnny responds, what should I say? Was I confident that those now very old web pictures wouldn't cause any trouble?

It was two days later when Johnny accepted my friend request and sent a brief note saying he hoped all was well and that we looked like life was going well based on the pictures on our social media site. I sent a note. All is well Johnnyboy, but I'd like to ask you a few questions. Could you give me a call at my cell number.

I got a quick note back saying, "I'll call at 9:00 PM."

I had assumed that the Johnnyboy reference would clue him in too the nature of my inquiry. The call arrived promptly at nine. Before I could say anything, Johnny was apologizing and confessing that he had taken photos from his bedroom window with his deceased father's SLR camera and telephoto lens. He was so nervous and felt so guilty that he didn't develop the film until five years later when he took a photography class. he subsequently scanned the photos to a digital file and destroyed the negatives and prints. Everything was password protected and he swore he never intended to do anything to hurt Monica. He was extremely appreciative for everything she had done for him and his mother and apologized for being a horny teenage male at the time. He admitted that Monica was so attractive that he couldn't resist watching and taking pictures when he noticed what was going on on our backyard deck. The website posting was another weak moment, but he defended himself by saying that he cropped and blurred the images so that no harm would come of it.

I acknowledged that nobody else would ever be able to recognize the photos and that if it hadn't been for the four distinct outfits in sequence, I wouldn't have even notice myself. I did, however, expressed my concern that I wanted to make sure he never had any more weak moments. I inquired as to how many photos he took. He admitted to 24 photos, several of each outfit some zooming in for close-ups and others with the normal focus. He acknowledged that the low light made the last set of photos pretty poor quality.

I made him swear that he would destroy the files after sending me a compressed password protected file. I knew it was actually unlikely he would really destroy the files, but he was on notice should anything ever come of them. He asked if he should try to have the pictures removed from the website. I paused momentarily then told him I would let him know after I showed Monica. He ended the call apologizing again and hoping that Monica would forgive him.

It was four days later when I got back to town and headed home on a Friday evening. After a nice dinner and an update on the kids' activities and the weekend plans my wife and I sat in the family room with a glass of wine. I asked Monica if she recalled the neighbors next door who had moved away several years ago. She responded," Of course, we exchange Christmas cards every year, why do you ask?"

I told her I understood that Johnny, the young man she had tutored, was studying accounting at Ohio State. She said she hadn't heard that and wondered how I knew.

I asked her to come sit by me as I wanted to show her some pictures on my laptop. I told her I had quite a story to tell her, and I handed her a Margarita. "Remember that night you were in my wet T shirt contest on the deck? Well as it turns out I wasn't the only one in the audience - thousands of people have witnessed your one-person wet T shirt contest. And while I thought your winning outfit was the tiny T shirt and titty flash, your black skirt and shear white blouse got the most votes."

Monica's mouth dropped as I open the first image.

It took her a few days to wrap her head around the whole situation. She actually seemed quite pleased with the number of positive comments and pretty tolerant of some of the crude things young man would say when viewing images of a very hot MILF. Also, pretty tolerant as I teased her about the amateur night wet nightie contest at the adult entertainment club in the next town 70 miles down the interstate.