A Fun Wedding Night

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Young best man smitten by mature woman.
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Disclaimer: This story is based on a real life experience. It was been enhanced in certain areas. All characters involved are over the age of 18.

*****

I was 19 years old when my cousin Mike, also 19, and my best friend since birth, told me he was going to get married. I thought he was crazy and told him so. We had done everything together and I knew that would change once he got married. Call it selfish but that's how I felt.

I didn't stay mad long, and agreed to be his best man. I had six months to try to change his mind, but I knew I would not succeed. Once his mind is made up that's how it's going to be, and that's' that.

We were both in good shape physically, but decided to spend the next few months getting buffed up for the wedding. So we spent a lot of time at the gym.

Mike is 5' 10", weighs 180 lbs, with blond hair and blue eyes. He's a handsome guy and had lots of chicks in high school, that's why I thought he was nuts for wanting to get married a year after we got out of school. Anyway...

I'm 5' 8" and weigh 175, with black hair and green eyes. I didn't have as many girls as he did in school but I did ok. My tastes were more towards the older mature women, and he kidded me a lot about the women I would try to pick up. He was witness to a few of my mature conquests, and his favorite joke was telling me I should hang out around retirement homes since I liked them older. Funny guy.

As the wedding neared, he was telling me all the people his fiancé was inviting. Aunts, uncles, and cousins from all over the place. They were all going to stay at a local hotel that was right next to a dining/function hall where the reception would be.

So the big day arrives and my silly cousin goes through with it and gets married. We're at the reception doing all the usual things you have to do. Being Best Man I was in the greeting line when this mature goddess comes by and introduces herself as Lorna. She is the aunt of my cousin's new wife's mother. I figured her for mid to late 50's and very well preserved if you know what I mean. A little plump but so curvy in all the right places. And the knee length dress she had on was having a hard time hiding a voluptuous body.

Needless to say I was smitten. Mike saw the way I looked at her and greeted her. He gave me a look and said, "Jack, she's family to my new wife, behave!"

I laughed it off and said, "Oh come on Mike, you know I wouldn't do anything to ruin your big day."

He shook his head as we both watched her walk away. "Yeah, well, see to it that you don't," he muttered.

I watched her all during the meal. I wanted to go sit with her but had to sit at the head table. She noticed me looking at her a couple of times, but only gave a polite smile, then looked away. I was dying for the meal to end so I could go have a drink with her, maybe a dance, and maybe whatever. Who cares what Mike said.

As soon as it was appropriate, I left the head table and started to mingle. Greeting people at tables and making small talk. I smiled at her a few times as I made the rounds to all the other tables, saving her table for last. A lady sitting beside her got up and walked away, and I went to her table and stood over the seat.

"Hi there," I smiled as she looked up at me, "Lorna right?"

"Yes, and you're Jack right?"

"That's me," I said as I pulled the chair out a little. "Do you mind if I sit for a few, I'm beat from all this mingling."

"Not at all," she replied as I sat down and turned to her.

"Nice wedding right?" I asked, letting my eyes wander over her body. " Are you enjoying yourself so far?"

"Yes I am," she said as she watched Mike and Lynn share a kiss as people clinked their glasses. "Mike seems like a very nice boy, and I'm so happy for Lynn."

I let my eyes wander over her body again, then smiled at her. "Well, we're both 20 now so I hope you don't think I'm a nice boy too."

She waved a hand at me and laughed. "At my age, you're still a young boy to me."

"Well, I'm old enough to drink, so can I get you another glass of wine while I get myself a drink?" I asked, indicating her almost empty wine glass.

She smiled then emptied her glass. "That would be very nice of you young man." Then she winked at me and said "is that better than a nice boy?"

I winked back and said, "much better," and left to get new drinks. I got her a white wine and ordered a Crown and Coke, and told the bartender to give me a double shot of Crown, which I downed at the bar, then made my way back to the table, where she was still sitting by herself now.

Handing her the glass of wine, I edged my chair a little closer to her and sat down, raising my glass in a toast. "To a fun wedding night" I said, as we clinked glasses and drank to it.

She continued to watch Mike and Lynn, then wistfully commented, "all wedding nights are fun."

When she looked over at me I grinned. "I wasn't talking about them," and winked at her again.

She laughed again. "Oh stop," she replied, "Don't you have a girlfriend here? You need to go have fun with her and leave this old lady to her wine."

I looked around the room, and caught a stink eye look from Mike. I ignored him and turned to her. "Not one of these young girls is my girlfriend. I'm single at the moment."

"Well", she replied, "I'm sure there is someone here that you will have a better time with than me. I'm just a divorced old lady here to see my grand niece get married, then it's back to my humdrum life of gardening and reading."

"How about a dance then, surely you're not too old to dance are you?" I asked, grinning at her teasingly while letting my eyes wander to her cleavage. There wasn't a lot showing, but enough to know there was a lot to be seen, if I got the chance.

She gave me a look for about 30 seconds, and then said, "You're not kidding are you?"

"Absolutely not!" I said emphatically. "I would love to dance with you. It will be fun, don't you think?"

She looked to the dance floor where people were boogying away, and said "I'm not dancing to this. If you're serious, we can dance the next slow tune they play. That's all the dancing I want to do."

We chatted for a bit about what my plans were for the future, yada yada yada, and then hit the dance floor when a slow tune was played. The first dance was one hand on hip, other hands held up shoulder high, like some ballroom waltz or something. I tried to get closer to her and she looked me in the eyes and said, "Easy young man, I have a reputation to watch out for here."

I laughed and said, "I'm not trying to get fresh; we just don't dance like this these days. It's different for sure. Maybe we can try my way on the next one?"

"When they play another slow one we'll see," she said as the song ended.

We walked off the dance floor and I said, "I'll get another drink and meet you back at the table."

I ordered another round and a single shot of Crown this time, and was making my way back to the table when Mike appeared out of nowhere. "What do you think you're doing?" he hissed at me.

"What!" I replied." I'm just having a drink with her moms' aunt and being nice to her. She's alone you know."

"I know what you're up to," he said. "I see you getting your shots. Getting ready to try to seduce another granny?" he asked.

"Hey, Mike," I said, giving him my best innocent look. "I'm just being a nice guy. Don't worry about it. She's brushing me off anyway. Thinks I'm a "nice boy."

"Yeah, well make sure you stay a nice boy, you hear me?" And he walked off to get back to his wedding, leaving me to get back to my granny.

I grinned from ear to ear as I handed her the wine glass, sitting down again, getting a nice view of her upper thigh as her knee length dress was hiked up a little from her legs being crossed. I looked long enough to make sure she saw me looking, then smiled at her again as I sipped my drink.

"Tell me Jack; just how old do you think I am. Honestly now?" she asked, after my long look at her legs.

"Well, I'll take a guess and say early to mid 50's?"

She laughed hard and said, "Aren't you the sweet charmer."

"Am I close?" I asked, honestly thinking she was more like late 50's, but I didn't want to hurt her feelings if I was way off.

"I'm not going to say," she said, as another slow song started up. "Come on," she said, getting up again. "Let's see how you young kids dance these days," and we walked out to the dance floor.

I took both her hands and placed them on my hips, and put one hand on her hip and the other on her back, and tried to pull her to me. She left her hands there but wouldn't come in close enough for our bodies to touch. "This is better," I said as I smiled down at her. "We like to get real close and rub up against each other, but this will do for now."

She looked at me and said, "I'd need more wine for that, and not be in a crowded family environment."

I stared at her and said, "Does that mean we can try it somewhere else, like away from all these prying eyes?"

She didn't answer for a full minute. She danced and continued to look at me, trying to figure me out I guess. "You're serious aren't you?" she asked, being very serious herself. "You're actually trying to pick me up?"

"I'm dead serious," I replied, staring in her eyes. "And yes, I am trying to pick you up. I was wondering when you were going to catch on," laughing as I said it.

She was not laughing. Just swaying as she looked at me until the song ended. "I'm going to the ladies room, I'll meet you back at the table," she said, and walked off the dance floor.

When she came back her face looked flushed, and she sat down and sipped her wine, then looked at me. "I want you to get up in a few minutes and leave. Go mingle. Dance with some nice young girl. Have some fun," she said.

I thought she was brushing me off and the disappointment showed on my face. Then she smiled and took my hand in hers, like she was shaking it, and passed me her spare room card key. "I'm glad I took both of them with me when I left the room. If you're serious, come to the room when you're done. I'm going to feign drunkenness and say I'm tired, and go back to my room in a little while. OK?"

Well, I'll tell you. You couldn't have slapped the smile off my face as I took the card key and smiled at her as I stood up. "Thank you for the dances," I said, loud enough for others to hear. "It was nice meeting you and I hope you feel better. Have a nice night!" I then kissed the back of her hand and left her at the table.

She left about 20 minutes later and I stayed another hour and a half. All the fun wedding stuff was over. Garter belts and bouquet throwing, and people were dancing and having a grand old time. Mike was thrilled that I was dancing with other girls here and there, and all was well with his world.

I had been drinking straight coke since she left, but acting drunk so I had an excuse when I wanted to leave. I made my way to Mike and hugged him and kissed his cheek, and hugged and kissed his new wife, and told them I was bombed and had to go. I wished them well and made my way to the hotel across the parking lot. I had no clue what was in store but I was so excited I thought I was going to cum in my pants on the way over.

I knocked lightly on the door, then used the card key and let myself in. The room was dark except for the TV and the bedside table lamp. She was lying on top of the covers in the hotel terry cloth robe, reading a book, looking very sexy with her reading glasses and her shoulder length hair pulled up in a bun on her head.

"I was starting to think you were only toying with an old lady," she said as she put the book down and stared at me. "And now here you are. I have to say I'm very nervous. I've never done anything like this in my life!"

"Well, this isn't my first time with an older woman," I said, taking my tux off and hanging it on the back of the chair then sitting down. "But it is the first time with one as hot and sexy as you are."

"You can stop with the charm Jack, you're here. I'm here," she said, blushing and shifting around nervously.

"I'm dead serious," I said, getting up from the chair and sitting on the side of the bed, resting my hand on her thigh and rubbing it. "You've been driving me crazy since I saw you!"

She smiled and put her hand on mine, rubbing it gently. "Well, you are certainly persistent, that's for sure. I thought you were just being nice to an old lady, but then I realized you were actually trying to pick me up. It was very flattering to an old woman like me Jack."

"Stop saying that!" I said as I rubbed her leg more, letting my hand slide to her inner thigh, squeezing it gently and moving closer to her. "I'm going to kiss you," I said, as I leaned in and kissed her lips. Just a peck, then another one, then holding one a little longer, letting my tongue snake out and feel her lips, as both of us were shaking with excitement.

She laughed nervously and said, "my God!"," I can't believe I'm doing this. You're young enough to be my grandson for God's sake."

I looked are her and said "grandson? No way! How old are you, really?"

She smiled and said "not now Jack, kiss me again before I change my mind."

I put my arms around her and pulled her to me as we kissed, harder this time. Sliding my tongue in her mouth as she moaned, then she stuck her tongue in my mouth and I sucked on it hungrily. She broke the kiss and said, "Oh my, so that's how you kids are kissing these days?" "I've never had my tongue sucked like that before."

"Did you like it?" I asked. "I love kissing like that. The longer and hotter and wetter the better for me" I said.

"Well I certainly think I could get used to it she replied. " "And yes, Jack, I liked it very much."

We kissed again, sucking tongues back and forth, getting hotter and hotter. I then kissed her cheek, then her neck, moving to her throat as my hand reached up and cupped her breast, squeezing it as she moaned and held my head in her hands.

I kissed my way down her chest, spreading her robe open as I went, finding a very nice lacy bra holding huge soft mature breasts. 40E as I later found out. I pushed her bra up over her tit and let it fall out, then attacked her nipple, sucking it as I squeezed and massaged her big soft tit.

'Oh God Jack, yes, suck it, oh my, it's been so long," as she held my head, watching me suck her nipple as it got hard.

I spread her robe open and pushed her bra up over her other tit, grabbing both with my hands and squeezing and kneading them as I sucked one nipple, then the other, pinching and rolling one nipple between my fingers as I sucked the other one. She was moaning and writhing on the bed as she held my head and encouraged me to keep sucking.

"Oh yesss, that's' it, pinch it, harder Jack, pinch it harder, mmmm, suck it, oh my god, that feels so good!"

I slid my hand over her belly, down to her panties, rubbing her pussy as I continued to suck her nipples. She jumped when my hand touched her pussy, and cried out, "Oh my God," as I rubbed her pussy while sucking her nipples.

As I started to kiss my way down her belly, she held my head and said, "No Jack, I rarely did that with my husband and I don't enjoy it."

I looked up at her as I kept kissing her belly, slowly going lower and lower. "I love to do it Lorna, and maybe it was never done right." I smiled at her as I kissed her panty covered pussy, and looked at her pleadingly. "Please? If you don't like it I'll stop, I promise. I just want to taste you."

"Oh my God," she cried, as she covered her eyes. "Go ahead," she said. "I've never enjoyed it and I don't think I'll start now."

She kept her hands over her eyes as I slid her panties off, then spread her legs and lay down between them, my face inches away from her hairy pussy. I waited for her to look at me, then smiled as I leaned in and kissed her pussy again and again. She watched me as I spread her lips with my fingers and licked her again. She moaned, then gasped when I slipped my tongue between her lips and licked her pussy from bottom to top, over and over, circling my tongue around and around her clit.

"Oh God!" she cried out as she ran her fingers through my hair. "That feels amazing, don't stop, lick me, just like that Jack."

I continued to lick her pussy. It got extremely wet very fast, and I kissed and licked her, then sucked on her clit as she writhed on the bed, her body shaking as she held my head by my hair. I stuck my tongue in her pussy as deep as I could, again and again, and she gasped and cried out "oh my goodness! That feels wonderful, don't stop Jack, you're going to make me climax."

I kept fucking her pussy with my tongue and could tell she was going to cum. She was breathing faster and faster, and thrashing around as she held me by the hair. I moved up to suck on her clit as I thrust 2 fingers in her pussy, sliding them in and out.

"OH my God! Yesss, like that! Don't stop Jack, I'm going to climax!"

I sucked her clit and fingered her pussy in and out as she let out a guttural moan, and came so hard. Her body shaking and thrashing as she held my head tight to her pussy, sucking her clit as she came.

"Oh my God, oh my God, yessssss, right there Jack...yessss!"

She pulled my head away from her pussy as her body shook. "Stop, please, oh my God, I'm so sensitive. I can't believe that happened!"

I laid there waiting for her to settle down. She was looking at me as her breathing slowed. "That was truly amazing young man. My ex only did that a few times in all our years, and NEVER like you just did it."

I smiled at her. "You have to love to do it for it to be good I guess, and I love to do it."

"Well it shows Jack. And you are very good at it."

"What about you?" I asked, grinning at her. Do you enjoy doing oral sex on a man?"

"I did it for him, a lot more than he did it for me, but I can't say I enjoyed it. I did it because I felt I should. He was a very selfish man."

I got up off the bed and started to undress as she watched me. Taking my time as I looked at her, lying there with her robe open and her bra pushed up over her tits.

"Take your bra off, and the robe please. I'd like to see you naked if that's ok with you."

She hesitated, watching me as I slowly took my pants off, then my boxer briefs, smiling at her as my hard cock sprang out in front of me. My cock is average I guess, 6.5 inches, not fat, but with a nice curve to the left. She stared at it as she took the robe off, then unhooked her bra and tossed it to the side.

I stood on the side of the bed and took my cock in my hand. Her eyes were glued to my hand as I stroked it slowly. "Would you like to do it for me now?"

She reached over and took my cock in her hand, squeezing it and then stroking it back and forth, her eyes never leaving it. Without looking at me, she said, "yes, I would like to do it for you now, right now."

I got up on the bed and kneeled beside her head as she lay down on her side with her head on the pillow. I leaned in so my cock was in her face, and she opened her mouth and sucked the head. I moaned. She moaned. She kissed the head, and then sucked it again, tentatively. Her hand stroking it back and forth.

"Oh yess Lorna, that's it. Just like that," I said as she started to take me in her mouth. "Suck it. Please. That feels so good!"

She held my cock with one hand as she sucked the head, taking a little more in her mouth, then backing off, then sucking it in again. I was so excited and felt like I was going to cum any minute.

"Oh my God, that feels so good. I think I'm going to cum. I can't help it," I cried out as I held her head and pumped my cock in and out of her mouth.

She moaned as she sucked me. Stroking it with her hand and sucking faster. Her head bobbed up and down on my cock, taking it in more and more as she sucked me. I was moaning and holding her by her hair, thrusting my hips as my excitement built.

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