Dianna's Awakening Ch. 05

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Dianna's First Swinger's Party.
16.2k words
3.92
12.6k
16

Part 5 of the 7 part series

Updated 06/10/2023
Created 08/10/2021
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Paul and I hadn't talked for several days since he moved into the spare bedroom, and I saw no need to let him know I was going out Saturday morning as I watched him mow the lawn. The anticipation of attending my first private swinger's party with Jerry later that night spurred me on. I wanted to wear something sultry and was on a mission to purchase just that. I usually do my clothes shopping at either Target or Walmart, but I doubted those two places would carry what, in my mind, would fit the bill for the evening.

Arriving at the local mall just after ten would permit me to leisurely shop for just the right outfit. I knew that I wanted something slinky with a zipper on the back so that when the time arrived for me to slip out of my dress, I could do so with needing to yank it up over my head, and for tonight black was my color of choice. I found a swanky boutique that had what I was looking for displayed in their window and entered the shop. I was greeted by a youthful-looking girl who asked, "Can I help you today?"

"I'd like to look around a little, please," I replied.

She smiled at me and said, "Take all the time you need." then returned to her early morning duties.

I began looking through their assortment of short black evening dresses and found several I wanted to consider.

"Can you direct me to the changing rooms, please," I said to the young girl working the early shift.

She pointed me in the right direction but said, "We only allow two garments at a time in the changing rooms."

I hung my least favorite on the return rack and took the other two inside. Slipping off my clothes, I decided to try them without a bra. The first dress was a kind of glittery fabric that hugged my hips and legs very nicely, and the material felt sensual as it slipped over my naked breasts. Its length nearly reached my knees, and I turned to see how it looked from behind. I was happy with the way the dress accentuated my shapely ass. Never having attended one of these parties, I wondered if the glittery fabric might be a little overboard. Slipping out of the dress, I moved to my second choice, a clingy fabric that also hugged my hips, but this dress had a more profound plunge in front as well as behind. I could easily reach around and unzip it at the appropriate time. It was shorter than the first covering my legs to mid-thigh. Like the first dress, this one also showed off my ass quite nicely. It was a little pricey, but I figured, what the hell, I could wear it when I met a man for the first time, or to a hotel meet and greet sometime in the future.

As I exited the dressing room, the young salesgirl asked, "Find something you like?"

I held the dress up and said, "I'm going to take this one, but I also need some sexy lingerie to go with it."

She smiled and replied, "Follow me."

As we approached their lingerie selection, she turned, and as she walked backward, asked, "How sexy were you thinking of?"

I didn't know there were degrees of sexiness when it came to lingerie, so I replied, "I don't want to look like a slut."

She grinned and tried to explain, "With the dress, you're buying the length will allow the tops of thigh-high stockings to show, and depending on how you sit, I suspect your skin above will also show."

"Okay, so what do you suggest?" I asked.

She reached for a small package and handed it to me. "These are designed to go higher on your legs," she said.

I looked at the photo of the hosiery on the package. The stockings were longer, but unlike regular pantyhose, the part that usually covers your ass was missing. The model on the package was taller than me, and the picture featured her from behind with the straps pulled high on her hips.

"Sexy but elegant," I said.

The salesgirl smiled and then said, "If you match these up to a satin or lace thong you'll not only feel sexy all night, but when the time is right, and you let that slinky dress slide off you'll be able to make any man or woman's heart skip a beat.

"Okay, I'll take these also," I said, handing her the tiny package.

Her grin broadened a little before she said, "Do you want to look at thong and bra sets?"

"What the hell, I might as well go all in, this is for a special occasion," I said.

We walked a short distance to that section of their lingerie offerings, "Satin or lacy," she said.

"I think satin with some lace trim would be nice," I replied.

She thought for a moment then asked, "What cup size are you?"

I replied, "I'm a C cup."

"You're in luck," she said as she moved to the clearance section.

"I think this will fit you perfectly," she said as she pulled a black set from the rack.

I took it from her and looked it over, the thong and bra were both of black satin but featured tiny black lace trim along all the important edges.

"I love it!" I exclaimed.

"And it's fifty percent off," the young girl said.

"Sold," I answered.

As she rang up my purchases, she said, "You know this outfit screams for heels, the highest you can stand in."

"You don't sell shoes?" I asked.

She smiled and said, "No, but I think you can find exactly what you need at my friends shop across the mall."

"Thanks so much for your help today," I said.

"No problem, your total is one hundred seventy-nine dollars, how would you like to pay?" She said.

I handed her my credit card, and as she ran the card said, "Tell Mark that Julie sent you."

Thanks again, Julie," I said as I gathered my purchases and headed back into the mall.

I giggled as I walked across the mall, thinking I'd need to intercept that credit card statement when it arrives so I wouldn't need to explain my purchases to Paul.

It was easy enough to find Mark's shop since the displays in front featured some of the highest and sexiest stilettos I'd ever seen.

"Hi, are you Mark?" I asked the sole salesman in the place as I entered.

He looked at me with a "do I know you" expression on his face then said, "I am."

I smiled and replied, "Julie says you can help me with some sexy high heels."

He grinned happily, knowing that his friend was sending some business in his direction before, he said, "I sure can."

"Come on in and have a seat, let's check your size," Mark suggested.

As I sat down, he asked, "What's the highest heel you've ever worn?"

"Never measured them, but about the height of those over there," I replied, pointing toward a pair of white pumps on a display table across from where I sat.

Mark continued his questions, asking, "Will you be dancing or just looking hot and sexy?"

I doubted there is much dancing at a swinger party, so I answered, "I suspect I'll just be lookin' hot and sexy." Using his exact phrase to describe what I'll be doing.

As we talked, Mark had already slipped my pump off and measured my foot. "You're a perfect size five, did you think about the color?" He asked.

"Nothing sexier than black," I answered.

"Couldn't agree more," he said with a broad grin on his lips.

"Give me a minute," Mark said.

He rose from his fitting stool and scurried into the stock room. I thought to myself, what is it about ladies' shoe salesman that makes them so appealing. It has to have something to do with the position they are in while waiting on you.

Mark returned with a stack of shoeboxes, and as he sat down in front of me, he said, "We'll start with ultra-high and work our way down until you feel comfortable walking in them.

He opened the first box, which was wider than all the others, and I could instantly see why. It contained a pair of black leather stilettos that had at least a six-inch heel. I could see myself falling off these as I tried to walk, but knew they would provide the best fuck me handles of all the rest.

"These will take some practice to walk in," he said as he slipped the sexy shoes onto my feet.

I stood up and almost fell into him. "I think we'll need to drop down an inch or two," I said without even trying to walk to the angled mirror at the end of the row of chairs.

He removed the fuck me stilettos and slipped them back into the box. "Let's try these," he said as he flipped the lid off the second pair.

This box contained a very sexy pair of shoes with about a four-inch heel that featured an ankle strap. As he lifted them from the box, I noticed that the soles were a bright red color, a feature that I knew would attract lustful stares from all the men in attendance at the party.

He carefully sipped my feet into the heels and then slowly attached the strap around my ankle, his fingers lingering just a little longer than necessary.

I stood up and slowly walked to the mirror, twisting my feet so I could get a good look at them from both sides and behind. The red soles would undoubtedly entice the look when I sat down and crossed my shapely legs.

As I walked back toward him, Mark said, "I have the same style with a five-inch heel if you're feeling more adventurous."

I knew another inch would do little to enhance the shapely look of my legs, and besides, when I was viewing them in the mirror, I notice how this pair make my calf muscles appear sexier.

"How much," I asked.

Mark smiled and replied, "We have a ten percent off sale until noon every day, so I can let you have these for sixty-nine ninety-nine."

"Sold," I said, smiling broadly at him.

With one more swipe of my credit card, I was set for tonight.

As I left, I noticed Julie standing at the entrance of her shop. I smiled and gave her a thumbs sign, up letting her know that Mark as fixed me up with a very sexy pair of stilettos.

It was about eleven-thirty when I left the mall and decided to grab a bite to eat before heading home.

I pulled into our driveway about one and noticed Paul's car was missing. Perfect timing, I thought, knowing I'd be able to take my new clothes up to my bedroom and not have him asking a bunch of questions about what I purchased.

I entered the kitchen and found a note Paul had left me. It read, "Dianna, I finished the lawn and decided to get a round of golf in this afternoon. I'll probably stop afterward for something to eat so you'll have to fend for yourself, see you around eight or so."

I smiled, knowing I could dress and leave before he got home avoiding his questions about where and who I was going to be with tonight.

As I puttered around the house, those butterflies of anticipation began in my stomach, which surprised me some since earlier this week, I entered Excitement Video full of confidence about the events I knew would happen. I suspect the newness of attending my first real swinger's party had something to do with those feelings.

About four-thirty, I began preparations for the party, showering and shampooing my hair first. I dried and curled my hair then brushed it into a seductive wavy look. I wanted my make-up to appear sultry, so I applied a dark shade of eye shadow my regular foundation and a blush that gave my cheeks a rosy appearance. I love my eyelashes looking long and sexy, so I applied more mascara then necessary, giving my eyes a provocative come-hither look. The pièce de résistance was my lip gloss, a bright red color that perfectly matched the soles of my stilettos.

Gazing at my reflection in the mirror, I thought, not too shabby for a forty-five-year-old mother of two.

Moving on to what I hoped would entice Jerry and all the other men in attendance, I slipped my new crotchless pantyhose over my feet and pulled them up over my shapely ass. I loved how the creamy white color of my flesh contrast with the dark material of my hose. Next, I stepped into the sexy little satin and lace thong, which covered my pubic hair and slithered between my ass cheeks. I wanted to see how I looked wearing just the hosiery and thong with my new stilettos, so I slipped on my shoes and carefully attached the thin straps around my ankles. Walking across the room toward the full-length mirror on the back of my bathroom door, I was happily surprised at the reflection I saw. My long shapely legs and creamy smooth ass looked breathtaking, and I imaged seeing my sexy stilettos pointed toward the ceiling later.

I moved back across the room and put on the matching bra, the thin wisp of lace trimming the cups served to enhance the smooth pale flesh above. I was very quickly feeling sexier and sexier as the minutes passed. The final piece of my seductive outfit was that slinky black dress, I carefully stepped into it and drew it up over my shoulders. With the zipper behind still open, it looked very inviting, but when I drew the zipper up, the sexy dress hugged every part of my form. Again, I moved in front of my mirror to survey the final look, a lovely, stunning woman reflected at me.

One final thing completed my preparations. I moved back to my make-up table and applied dabs of my favorite perfume behind each ear and in the soft flesh of my cleavage. The scent of Yves Saint Laurent Black Opium Vanilla perfume wafted into my nostrils, and I hoped it would do the same to every man I met tonight.

Gathering my essentials in a small black leather clutch handbag, I headed downstairs, feeling more excited as the moments passed. It was almost six o'clock as I stepped into the kitchen. I recalled from when Jerry and I first met the drive to O'Neil's took about thirty minutes, and his place was another ten minutes from there. If I left, now I'd arrive about twenty minutes before seven. I hoped that my early arrival would provide me with a few moments alone with Jerry before the other woman showed up.

Traffic was horrendous, and it was nearly a quarter till seven when I drove past O'Neil's, so much for getting to his place early, I thought. I pulled up to his apartment building and noticed a fancy little red sports car parked outside. I parked my family minivan beyond and slipped out of the driver's seat. As I climbed the concrete stairs to his apartment, I assumed the sports car belonged to my competition for his affection tonight. I lightly knocked on his door, and in a moment, Jerry opened it. A broad smile came to his lips as he said, "Dianna, you look impeccable tonight."

He gave me a quick kiss on the cheek and said, "Come in and meet Saundra."

She smiled at me and started sauntering across the room. Saundra was at least four inches taller than me, her platinum blonde hair shorter than my brunette locks framed her face perfectly. She was long and lean and wore a tight red leather mini skirt and an even tighter white tank top with the word "Sexy" brazened across her massive tits. Her shoes had that same 'fuck me" look that Mark had shown me earlier this morning, but instead of black, hers were bright red.

Saundra stretched out her red-tipped fingers, and as we shook hands, said, "You ready to have to fun tonight, darlin."

I smiled back at her and replied, "I hope to."

Jerry turned to Saundra and said, "I've told Dianna how we met."

She smiled and said, "He was my knight in shining armor, helping me with my grocery bags when I could hardly walk on my broken little toe."

"He is quite the gentleman," I said, knowing this was the woman who introduced Jerry to the swinger lifestyle.

Jerry glanced at his watch and said, "Enough chit chat ladies, you can better acquainted once we get to the party."

Saundra grabbed her red leather jacket as we headed for the door. Once outside, she stopped at the top of the stair and said, "Jerry, hold my hand. These stairs scare me."

I kind of giggled to myself, knowing that even this sexy blonde bombshell was a little worried about falling off her six-inch "fuck me" stilettos.

I followed them down the stairs feeling a little like the third wheel in the group, a feeling I'd not let ruin the rest of my night.

Once safely outside, Saundra announced that she would take her car and follow Jerry to the party's location. Jerry watched as she more or less struggled to get into that fancy red sports car, I'm sure he wanted to catch a glimpse of her sexy naked thighs.

"You ready for an exciting evening?" Jerry asked as he held the passenger door of his car for me.

"Absolutely," I replied.

After a few minutes of silence, Jerry reached over and placed his hand on my thigh and said, "Dianna, I want to apologize again for not calling you as I'd promised."

"Not to worry, hun, I've had some good times since our first night together," I replied.

He giggled a little then said, "Judging from your updated profile, I suspect you did."

"It's been an enlightening couple of weeks," I remarked.

Wanna fill me in?" Jerry asked.

I laughed and answered, "Why not."

I began by explaining that after he hadn't called me, I arranged to meet another member. "Stephen was spectacular, and we shared several firsts together," I said.

"Go on," Jerry urged.

"He took the photos I've posted and was the first man who ever fucked me wearing a condom. I can't tell you how exhilarating it was to feel his latex covered cock buried in my virgin asshole." I admitted.

"Wow, that's fuckin' hot," he remarked.

"On top of that, after he filled that latex sleeve, I enjoyed him feeding me the contents, his cum tasted so good," I said.

"Holy shit Dianna," Jerry said.

I'll send you the password to my private album so you can see the pictures he took after he filled my cunt with his rock-hard cock and pumped a second massive load of thick creamy cum inside my sopping wet cunt the photos show his load oozing out of me." I added.

Jerry squeezed my thigh a little then said, "You know every party I've been to, has a huge supply of condoms for those folks who avoid bareback fucking."

I laughed and said, "I'd love to feel a big hard cock covered in a ribbed latex condom slip deep in my throat."

I reached across and slipped my hand between his thighs to see if our conversation had the desired effect on his beautiful curved cock.

He giggled and said, "Yes, Dianna, you've got me hard already."

"How much longer before we arrive?" I asked.

"Long enough for you to fill me in on this glory-hole fantasy of yours," he said.

"Another fantasy fulfilled," I replied.

Jerry looked toward me and said, "Come on, darlin', give me the details."

"Okay, okay, you already know how much I love giving head." I started.

"Something you've made abundantly clear." He answered.

"Well, I recently visited a place called Excitement Video," I said.

He laughed and said, "I've been there."

"So you know the layout of the place. I made my way back into the stripper's room and grabbed the first guy I could and told him I was there to have a good time and swallow some hot, thick cum." I explained.

"Fuckin' hot!" Jerry exclaimed.

"He was the first of thirteen anonymous cocks I sucked off that night, filling my belly with more cum than even I thought possible," I said.

"Why do I suspect there's more to this story?" Jerry asked.

"After all those blowjobs, I still wanted more, and I went into the dancer's room and found my first big black cock. I fucked him silly stuffing his massive shaft and huge mushroom-shaped cock head deep in my tight wet cunt." I admitted.

"Another fantasy checked off your list," Jerry remarked.

I giggled and said, "There's more after he filled me with hot cum I got down on my knees and announced to the gathered group that I wanted my first bukkake facial." I said.

"Holy shit Dianna," Jerry said.

"One by one, every guy there moved in front of me and jerked off splashing my face with so many loads that I lost count. I was covered with thick hot cum from my hair to my tits. My eyes burned from the cum they pooled in my eye sockets. I felt like such a cum slut." I admitted.

"Christ Dianna, that's amazing," he said.

"I felt disgusting, which is one reason I hadn't checked my messages for several days. I'm so glad I checked last night so that I can be with you and Saundra tonight." I said, hoping tonight would turn out better than Wednesday night.