Matts Wedding Week

From TSG: Thanks to 7ashie and MissZ for their editing skills. Together, they made this story much more enjoyable.

I had a hard time deciding on a category for this tale and decided on Loving Wives, although it could easily been included in Mature. There are elements of domination, voyeurism, exhibitionism and an anal sex scene. Enjoy!

*

"I don't fucking believe this," I thought to myself. I was sitting in the Marriott's restaurant having a late-morning breakfast with Mr. and Mrs. Wilson, my college roommate's parents, and three other older couples.

I let out a frustrated laugh. "Matt's really screwed me this time," I said out aloud. When I noticed the scowls from the older people, I continued, "I apologize for my language. I'm just caught off guard."

It was Wednesday morning in the middle of June and I was in Huntersville, NC, just west of Charlotte. I'd taken a week of vacation time and was attending Matt's wedding. Matt and I have been best friends ever since we met on our first day of college.

I was quickly learning that this wasn't simply a wedding, it was an event. Matt and I came from rich families, but he was marrying into serious wealth and as we all know, the wealthy are different.

I was invited to a "Kick-Off" party, which started at three. There were five other events planned before the wedding and reception on Saturday.

When I talked to Matt last week, he told me that the cocktail parties and receptions were casual. I packed shorts and golf shirts, a sport jacket and slacks for the rehearsal dinner and a suit for the wedding.

You can imagine my frustration when I learned that jacket and ties are the required dress for most of the events and that the wedding was a black tie affair.

I smiled at Mrs. Wilson and said, "I guess you'll have to cancel the wedding...'cause I plan on killing the groom as soon as I see him." The chuckles turned into uncontrolled laughter as Matt walked up to our table.

"I get the feeling, you're all laughing at my expense," Matt said as he greeted us.

When the laughter died down, I answered, "We're laughing at you, but it'll be at my expense by the time I finish my shopping."

"What did I do?" he asked, genuinely bewildered as everyone else howled again.

"Oh Matthew," his mother started.

"Don't worry about it Mrs. Wilson. If I had been smart, I would have called you and asked about the dress code. If you'll excuse me, I need to find a mall and do some serious shopping."

As I was getting ready to leave, Mrs. Lewis ("Please call me Jan.") asked, "Would you mind if I came along with you Chris? I also need to get some shopping done."

Jan's husband laughed. "You brought three suitcases full of clothes Jan. What else could you possibly need?"

"Hush, Joe." She looked at me again and raised an eyebrow.

"If you'll help me pick out a new wardrobe, I would be happy to have you along." I replied.

"As long as you're paying for it kid," Joe smirked.

Two hours and a small fortune later, we left Brooks Brothers. I had purchased a tux, two suits, and two pairs of slacks, shirts, ties and accessories. The on-premises tailor agreed to have two outfits ready in an hour. The remainder could be picked up the next day.

Jan and I stopped at Starbucks for a coffee. As we walked to a table I said, "I want to thank you for all your help. You really have incredible taste." I leaned in and kissed her cheek and was surprised when a blush spread across her face and chest.

She diverted her eyes and seemed to be embarrassed. Although Jan is double my twenty five years, she is a very attractive woman.

She's an athletic 5'3" and 120 lbs. She has very sexy grayish-white hair. It's cut short and groomed to perfection. Her eyes are blue and she has thick wide lips. Stylish and suave, Jan plays tennis and golf and is a regular at the gym. Her figure is a compact 35B, 25, 36 and it's no wonder that her legs and ass are her best features. Today she is displaying them in a black tennis skirt and white sneakers.

As we sipped our coffee, we discussed the week's festivities. Jan told me she needed accessories for the yellow sundress she was wearing to the kick-off party and for the black cocktail dress she was wearing later that evening to dinner at the country club.

While we were talking, a young mother stopped next to our table. She crouched next to her stroller and gave her daughter a milk bottle. As she bent over, her red thong was visible above her jeans.

As the mother walked away, Jan asked, "Do you think that's sexy?"

I noticed that the blush had returned. "Do I think what's sexy?"

"You know. Her underwear." Jan's blush deepened.

"Her thong? Yes. I think it's very sexy. Do you?"

"I've always wanted a thong. But Joe says that only sluts wear them." Jan bit her lip and diverted her eyes as she spoke. "Anyway, I need to do my shopping. Your clothes will be ready in forty-five minutes. Let's meet at the car in an hour."

When we arrived back at the Marriott, we unloaded our purchases and had the concierge take the packages to our rooms. As Jan and I reached the elevator, I pulled a wrapped present from the one bag I carried. I handed it to Jan. "I want to thank you again for your help and your company. I had a nice morning."

Jan was caught off guard. "Chris, this isn't necessary."

"It's my pleasure. And, if I could give you some advice, you might want to open it when you're alone."

The elevator stopped at the eighth floor. I kissed Jan's cheek and headed for my room.

As I walked down the corridor and into my room, I wondered if I had made a mistake. I almost expected an infuriated Jan to phone my room and curse me out.

Earlier, while I waited for the tailor to finish my clothes, I walked around the Mall. I had a wicked idea as I passed Victoria's Secret. Knowing I was out of line, but deciding to take a chance, I bought Jan two presents. For the afternoon kick-off party, I bought a pale yellow satin thong to match Jan's yellow sundress and settled on a black lace thong and black thigh highs to go with the black cocktail dress she planned to wear this evening at dinner.

I saw Jan three hours later at the party. It was held on a large cruise boat that slowly motored around Lake Norman. Jan was close at her husband's side, but every time I glanced her way, she was staring at me. When our eyes locked, Jan would quickly look away.

I was standing at the bar sipping a scotch a few minutes later when I heard a familiar voice, "How was your shopping trip?'' Joe approached me from behind with Jan following in a steady pace.

"It was fine, Joe. I found everything I needed and a few extra surprises." As I said the last part, I looked at Jan. She blushed again. "How was golfing?" I asked.

Joe started to answer, but saw a friend and abruptly walked away.

"Are you enjoying the cruise?" I asked Jan.

A quiet, "Yes," was all Jan said.

"We're lucky that it's such a beautiful day."

Jan merely nodded.

Jan's demure actions were arousing me. "So tell me. Is Joe right?"

"Is he right about what?"

I leaned in and whispered, "Does wearing a thong make you feel like a slut?"

"Yes," Jan said. "Oh God, I can't believe I said that." She stated and quickly walked away.

I moved from group to group over the next ninety minutes. When I saw Jan walk by, I reached for her arm and stopped her. Pulling her close, I whispered in her ear, "Follow me in two minutes. I want to see your thong."

Jan's eyes were wide as saucers as I walked to the stairs and climbed to the bottom deck. As it was such a beautiful day, the small group that was invited to the Kick-Off cruise was all on the top deck.

I had scouted the bottom deck earlier and waited by a storage room door. Jan looked like a prisoner being led to the gallows as she descended the stairs. I opened the unlocked storage room door and let Jan precede me into the room.

We stood eight feet apart and were facing each other. "Show me," was all I said.

Jan was staring at the floor and didn't move for a few seconds. Then she slowly nodded her head. She stretched her arms and reached for the knee length hem of her sundress. Taking a deep breath, Jan began to raise it up. When she reached her crotch and I could see the bottom of her thong, she stopped.

"Higher," I commanded.

"Yes," was her response. She pulled her dress up until she was exposed to her belly button. A pale yellow triangle covered her pubic mound and two strings arched over her hips.

I looked over the lower half of her body in silence, until I instructed, "Now from the back."

Her eyes never left the floor as she turned her back to me. Her hands gathered more of the hem and pulled it over her hips.

Jan's ass was truly magnificent. Two perfectly shaped globes were sexily split by the yellow string of her thong. I couldn't believe that this woman was fifty.

"Spread your legs and bend over."

My cock got rock hard as she spoke a quiet, "Yes, sir."

"Yes sir?" I couldn't believe her response. She was getting off on exposing herself to me.

Jan's ass spread before me. "Pull the thong from your ass."

Jan reached behind and pulled the string over her left globe. Without being ordered, she grabbed each cheek and pulled them apart. I could clearly see Jan's anus and the bottom of her wet vagina.

I studied every inch of Jan's body. I wanted to attack her, but knew that it wasn't the right time. "Will Joe be looking for you?" I asked.

"Yes. At some point."

"Turn around."

She straightened up, dropped her dress and turned to face me. She was looking at the floor as she said, "I really need to go."

"Okay, sweetheart. But first..." Jan's body visibly stiffened. Her eyes came up and she looked me in the eye. "But first, I want you to suck my cock."

Jan trembled. I unbuttoned my sport coat jacket and waited. She hesitated for another brief moment and then approached me. Not wanting to dirty herself, she squatted like a baseball catcher. My rock-hard eight-inch cock was straining against my pants as Jan ran her fingers over my bulge.

"Oh my God." Her fingers traced up and down my lump. "Good God. You're huge."

"Better hurry, before Joe finds us."

Jan unbuckled my belt, unbuttoned my pants and pulled them and my boxers to my ankles. My thick hard slab bobbed in front of her face.

"Oh Jesus. Oh God," was all Jan said before she opened her mouth wide and took half my cock. She attacked me and used her lips, tongue, cheeks and throat. I was trying to make Jan's blow job last, but was quickly losing control.

Jan was grasping my ass cheeks to maintain her balance. When she slid a finger into my crack and rubbed my asshole, I exploded and pumped my cum into her mouth. Pulling Jan to her feet, I kissed her. Our tongues explored each other's mouths.

Finally, she pushed me away. She wiped her hand over her mouth and said, "Please, can I go?"

I was amazed that this mature older woman was asking my permission to go back to her husband.

"Off course you can. Just remember though, I want you to wear the black thong and thigh highs tonight."

Jan nodded and then departed from the storage room.

Jan and I traded glances for the remainder of the boat party and again later that evening at the dinner. She looked stunning in the black cocktail style dress. Her pearl necklace hung across her upper chest and a small amount of cleavage was visible. As always, I was attracted to her legs and ass.

After dessert, a jazz band began to play swing music. The guests started to mingle again and I found myself in a small group of older guests. The discussion was boring, but I didn't want to be impolite, so I joined in. After a few minutes, Joe joined the group and Jan followed a short time later.

It was twenty minutes of mind-numbing conversation later that I was standing next to Jan. As the others were discussing ways to solve poverty, I leaned in and whispered to Jan, "Go to the ladies room, take off your thong and bring it to me."

Jan didn't look at me or acknowledge what I said. But after a few minutes, she excused herself and left for the bathroom.

I watched Jan's incredible body leave the dinning area. When I turned back to the group, I noticed that Mrs. Wilkes, another guest, was staring at me. She seemed to be watching as I stared at Jan. When we locked eyes, she gave me a slight smile and a wink.

The country club men's locker room was across the hall from the ladies' bathroom. When Jan came out, I was holding the locker room door open. I had checked earlier. It was empty and closed for the day.

Like earlier in the day, Jan demurely entered the room. As she passed me, I whispered, "Go to the back row of lockers."

Before following, I looked up and down the hallway to make sure we were undetected. I was surprised and a bit concerned when I saw Mrs. Wilkes peering around the corner. She nodded her head and smiled again.

Sally Wilkes was a decade younger than most of the other wives. Rumor had it that she was a trophy. She was an Amazon and stood a striking six feet tall. She had a curvy body with a huge 40+ chest and a come-fuck-me ass.

She was dressed in a stylish red dress with a hint of Oriental detail. The dress showed off a mouth watering amount of cleavage and almost five feet of spectacular legs.

We stared at each other for a few moments. Before breaking eye contact, I made sure Mrs. Wilkes saw me as I started to unbuckle my belt.

Jan was already in the back of the locker room when I caught up with her. I pointed at the thin wooden bench in the middle of the row of lockers. "Kneel," was my simple instruction.

Jan was able to place her left leg on the bench. She bent over and rested both hands, palms down on the top of the hard surface. Her right leg was spread wide and positioned on the locker room floor, allowing her to balance herself.

Her black, knee-length cocktail dress was stretched tight over her thighs and ass. As I started to run my hands over her prone body, I noticed movement out of the corner of my eye.

When I looked up, I saw Mrs. Wilkes, looking down the long row of lockers, to our aisle.

I continued to caress Jan's body as Mrs. Wilkes and I watched each other. When I pressed a single finger to my lips, indicating I wanted Mrs. Wilkes to be quiet, she nodded. I pointed to a spot three aisles away, which allowed Mrs. Wilkes to see the lower two thirds of Jan's frame as she knelt on the bench.

Continuing to run my hands along Jan's legs and dress-covered ass and looking Mrs. Wilkes in the eye, I asked, "Are you horny?"

Jan panted out a, "Oh God. I'm so fucking horny."

Still looking at Mrs. Wilkes, I raised an eyebrow. She nodded "Yes."

"Do you want me to fuck you?"

"I've been thinking of your big dick all day. I'm dripping. Please fuck me."

"Pull up your dress. Show me your pussy and ass."

Jan reached her left hand behind her. Still balancing in a doggie position on the bench, she pulled her black dress over her bottom. Her ass was naked and high in the air. Her muff was trimmed into a landing strip and her lips were bare, wet and swollen.

Looking over at Mrs. Wilkes, I pointed at the hem of her dress. She bit her lip in an embarrassing gesture, then nodded her head, took hold of the bottom of her dress and lifted it over her waist.

Mrs. Wilkes was wearing a pair of nude thigh highs and frilly red lace boy shorts. I mouthed, "More," and she pulled the crotch of her boy shorts to the side, showing me her full bush.

I reached between Jan's spread legs and with a feathery touch, slid my fingers along the wet swollen lips of her vagina.

Jan moaned, "Oh, Mother of God." She lowered her head and rested her cheek on the hard wood of the bench and circled her arms around, hugging the bench to her.

My fingers traced from Jan's pussy lips to her clit circling it lightly. Going back the other way, I didn't stop until I was rubbing Jan's exposed anus.

Jan shook in a small orgasm, "OOOOhhhh, so fucking gooooood."

Looking over at Mrs. Wilkes I mouthed, "Touch yourself."

Mrs. Wilkes silently slumped against a row of lockers, shuffled her feet further apart and rubbed two fingers along her slit. I noticed that she was biting her lip, to stop from making noise.

Using more pressure, I circled Jan's clit, "don't stop . . . don't stop . . . fucking, don't stoopppp," she begged.

Mrs. Wilkes was now pushing two fingers deep into her juicy cunt.

I mouthed, "Show me your ass."

She turned around, bent at the waist, lifted her dress and showed me a superb heart shaped butt. I could see her fingers still working in and out of her snatch as she leaned against the locker.

This was getting to be way too much for me. I didn't think I could explain being in the men's locker room of an exclusive country club, with two half-naked, married women. I needed to end this, but wanted to bust a nut first. I quickly dropped my pants and boxers to my ankles, lined up my rock hard dick with Jan's gaping pussy and plunged in with one hard stroke.

Jan's orgasm started before I hit bottom. Grabbing a hip in each hand, I pounded her from behind. Mrs. Wilkes must have been startled by the moaning, because she turned to watch.

I pounded Jan's snatch and as Mrs. Wilkes rubbed her own pussy, I pulled my stone-hard, thick eight-inches long dick from Jan's hole and let Mrs. Wilkes see it for the first time. It bobbed in the air for a second before Jan screeched, "Put it back in and fuck me!"

As I plunged back in, Jan started rubbing her clit with one hand. She was riding from one orgasm to the next as her juicy tunnel gripped my dick. As Jan frigged her clit, her fingers would dance across my swinging balls adding to my stimulation.

Mrs. Wilkes had worked three fingers into her cunt and was fingering herself hard. Her legs were spread and she was hunched against a locker.

I was holding on tight to Jan's hips. I spread her ass cheeks apart, so I could watch my rod pound into her twat. Her pussy was open wide as I thrust into her. I was mesmerized as her asshole winked with each thrust.

I slid one hand to her ass crack. It was slick from all our fucking. When I pushed my thumb against her rose, it sprang open and engulfed my entire thumb.

Jan moaned, "That feels so fucking nasty. Don't stop."

I looked at Mrs. Wilkes and she raised an eyebrow, wondering what I was doing.

While I fucked her cunt and fingered her asshole, I teased, "Do you like my thumb in your ass?"

Mrs. Wilkes eyes got wide and she fingered herself harder, when Jan moaned, "God yes. I love a full ass."

"You better relax, because my dick is coming next."

Jan sobbed as I pulled from her cunt. I rubbed my soaked cock along her ass crack. Looking over at Mrs. Wilkes, I was surprised to see that she had stopped fingering herself. Three fingers were embedded in her snatch and she seemed to be holding her breath to see what would happen next.

I smiled at Mrs. Wilkes as I lined my mushroom head against Jan's anus. As I pressed, Jan's asshole opened and I easily slid in. Her sphincter wrapped around my dick as I started a slow, hard fuck.

Jan babbled, "So full, so full, so fucking full."

She balanced herself on one hand and I could feel fingers press into her pussy. As I power-fucked her ass and Jan fingered her pussy, Mrs. Wilkes was back to finger banging her own cunt.

I silently mouthed, "Close?"

Mrs. Wilkes mouthed back, "Yes!" And I responded, "Together."

Then out loud, I told Jan, "I'm getting close, baby. I'm going to cum in your asshole."

"Oh yes . . . me too . . . me toooo . . . mmmeeeee tooooooo," she screamed and rocked along the bench.

My orgasm quickly built as Jan's vice like hole gripped me tight. I exploded and shouted, "AAArrrghhhh. Jesssssuuuussss."