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Sweet Dreams are Made of These
I played competitive soccer, not high league type but still pretty competitive. I'm pretty fit and started using a GPS fitness tracker vest on my friend's suggestion. It is capable of measuring all sorts of data. If you have ever watched soccer on the tube, then you know what I'm talking about. And yes, it looks like a bra.
And that's what my girlfriend teased me about it. When she'd do the laundry, she'd dangle my vest from her middle finger and ask me. "Hey Jackie! Are you sure this isn't a bra?" Or "Where do you want me to put your bra?"
"Ha ha, Jennifer. Very droll!" I replied as I snatched it from her. I really didn't like her calling me "Jackie" verse my given name Jacque. "It's probably more expensive than yours are."
It was a couple of weeks later when I packed my kit for a game. Running late, I grabbed my vest and gear atop the laundry pile and stuffed it into my bag along with the rest of my stuff, hopped into my car and sped off to the field. Traffic was horrid and it took almost an extra half hour to arrive. Most of the guys were already there and mostly changed. "Hey Jacks! They moved the start up because of the rainstorm that's coming. Supposed to be really bad lightening too."
"Shit! Bad enough to be late but moving the game time up too?" I swore to myself. I quickly stripped off. I frantically rummaged in my bag for my vest. It had settled at the bottom. I pulled it out and put it on. Shorts, shirt, socks and cleats. I ran out into the field to warm up. Ted the left back who suggested the vest, noticed I was twisting around a lot and asked if I was okay. "Yeah, this vest seems uncomfortably tight today. It will be okay."
Before the game started, I turned on the phone app for the vest then ran out to the field to take my position as right back. Ron was the middle back between us. You could feel the humidity in the air that was just waiting to dump on us. We just started the second half when the sky started getting dark and cloudy but no rain yet. Off in the distance, there was a low rumble from the approaching thunder.
Still nil-nil with about ten minutes of playtime left, there was a sudden boom of thunder. It was really close. The Referee immediately blew the whistle and instructed everyone to leave the field until the storm past. I was a bit cheesed and took my time only to get caught in the downpour. My white athletic shirt was almost transparent and my black vest clearly visible.
Back in the change room to wait, I peeled off my wet top and looked at my phone to read my vest data. Nothing. There was no record of anything. It wasn't even connecting. "Hey Ted. Something wrong here."
Ted came over. He made a funny face. When I looked at him quizzically, he said. "That's not your usual GPS vest. Did you get a new one? Why does the back of your vest say VSX?"
Ron took a look too. "I think my wife has one that says that. Um... VSX. Isn't that Victoria Secret?"
"What?" I reacted harshly. "Why would I... Victoria Secret doesn't make a GPS tracker. I..."
I stripped off the vest. And swore. "Fuck. This is Jenn's bra!"
The guys started to laugh.
Both teams decided we'd finish the game another day since we had lost our field time after the storm had finally past. I changed back to my street duds and drove home all the while thinking about wearing Jennifer's bra. Back home, I went to put my wet kit down in the laundry room. Jennifer was there ironing. I tried to hide and bury her bra beneath my gear but it fell to the floor. Jennifer giggled and dangled something from her finger. "What are you doing with my bra? Isn't this your bra?"
I muttered something but mostly ignored her. During dinner, she kept bugging me about it. Finally fed up and just to stop her. "It was with my stuff on the laundry pile. I just stuffed it into my bag before I left."
"Did you wear it?" She prodded and prodded.
I was reluctant to tell her because I knew she'd tease me about it forever. But she kept pushing and pushing. I was almost in tears. "YES! I wore it. It looked like my GPS vest."
"Oh, Jackie. I'm sorry. I didn't mean to tease you so badly." Jennifer gave me a warm hug. "But I was thinking it was kinda hot. I think you'd look cute in a bra. And maybe some panties. Oh and even some sexy lingerie."
I was still pissed at her and poured myself a number of scotches before going to bed. I guess I was drunker than I thought and started having this weird dream.
I found myself in the change room at the soccer field. I was standing on the bench fully clothed with the guys surrounding me. I removed my shirt and was wearing Jennifer's sports bra beneath. When I dropped my pants, I was wearing one of her black thongs. Then the guys all applauded and cheered. I awoke with a jolt and sweating.
I looked at the clock: three A. M. I then looked at Jennifer sleeping peacefully. I closed my eyes but I needed to piss. I flipped the covers and stood up. There was a huge tent formed in my PJ pants. Ever try to piss with a boner? Pee just goes everywhere.
I managed to soften a bit. Enough to piss but I sat to make sure everything went into the bowl. Done, I flushed the toilet and washed my hands. I splashed some water onto my face then went to grab I thought was a towel and rubbed my face. Rather than terry cloth, I instead grabbed Jennifer's stockings that she washed out the night before.
Jennifer hated pantyhose. For work or going out, she always wore stockings and garters. I loved them too. Plus it made it easier for us to fuck. I loved how Jennifer would rub her legs against me when I was between her thighs. Pantyhose just gets in the way.
Even though she had rinsed them out, I could still smell her sweet fragrance as I continued to rub the nylons against my skin. My erect returned with vengeance. It ached for relief. I dropped my pants and sat on the toilet cover. As I smelled her stockings, I took hold of my shaft and started stroking my seven inches. One of the legs slipped from my hand and kissed against my dick. The soft sensation was against my undershaft was new. I wrapped the stocking under my hand and continued my masturbation. It only took four or five more pumps before I shot my load. "Oh fuck! Uh! Uh! Uh!"
I panted pretty hard as I sat there to recover. My load had soaked into her stockings. "Oh fuck! That was... Fuck! I came so hard!"
Then. "Knock, knock. You okay in there Jackie? You've been there for a long bit."
I jolted myself back to the present. "Er... yeah. Be out in a minute."
My dick was still rock hard. I looked at her hose and needed to wash out the stains. When I opened the bathroom door to leave, Jennifer was waiting. "I need to go too."
I went back to bed. Jennifer returned a minute later, naked. She jumped on top of me and sucked my cock. Then she mounted me and slammed her ass into me until she came hard and collapsed. Having just orgasmed a few minutes ago, I was still able to go. I flipped her onto her back and punish fucked her until she came again and again and I was finally I was able to come inside of her.
Next morning when we awoke, Jennifer smiled and kissed me good morning. "Wow, Jackie. That was great last night. I've never cum so many times and you... You held on for almost ever."
She wasn't wrong. Usually, I'd cum inside her after about a minute or so and then she would make me eat her until she came.
All weekend, the thought of wearing Jennifer's bra and then nightmare (dream?) of stripping in front of the guys replayed in my head. Jenn of course continued to taunt me about it. Sunday night as we laid in bed, Jenn was dressed to fuck. Black lace bra and panties, black seamed stockings held up by an eight strap garter belt.
I barely got my clothes off before she pushed me onto the bed and mounted me. Her hot pussy rubbed against my hard undershaft. I reached up and unhooked her bra. She shrugged off the straps and let the bra slide into her hands. Rather than flipping it away, she placed it over my chest. I tried remove it but she leaned forward until her tits were against my chest and held my wrists to the bed. She continued to hump against me. It was then I realized her panties were crotchless and she was rubbing her dripping wet slit against me.
"Fuck, Jackie. You look so sexy!" She smiled deviously at me. "It makes me so fucking hot! You need to wear a bra more often!"
Jenn lifted her hips up as the knob of my cock slid along her slit until it popped in of her. She lowered herself until I was fully inside. She grinded her ass down and then. "Fuck, Jackie! Yes! Ah... Ah... Ah...!"
My crotch area was soaked. "Did she just squirt?"
Jennifer was not done yet. She started bouncing her ass up and down. It only took a few moments before she came again. "F... U... C... K...! Yes! Yes! Fuck, yes! Aaaaaa......"
With a final arch of her back, more squirt but this time bigger. Then she suddenly collapsed on top of me. I could feel her heaving as she breathed and the hard beat of her heart. And I hadn't even cum yet.
I rolled her onto her back and fucked her as hard as I could until I blew my load into her womb.
We both fell asleep exhausted. I rolled back to my side and where women usually had this issue, I instead laid in the wet spot. Jenn's slumber was peaceful but again I had that weird dream of being dressed in lingerie. This time, I found myself standing in our living room dressed in a classic French maid's outfit. A tight fitted, short dress flared skirt due to the huge amount of crinoline. The dress was strapless, off the shoulder that accentuated my big boobs ("I had boobs?") and deep cleavage. I wore black fishnets that were held up by thick straps of a garter belt and black CFM, platform, open-toed stilettos. Atop my head was a maid's cap. My face was still my face but make-up hid most of my male features.
In the room was Jennifer and some of her friends. I glided around to each providing them with stems of wine. Her BFF, Violette slid her hand between my legs and up under my skirt then squeezed my package. I awoke with a jolt. My dick was hard and still pulsed out my white, hot cum. I quickly dashed to the can and cleaned myself off. "What the fuck is going on with me?
Next morning, Jennifer kissed me and smiled. When I asked what, she told me. "That was so hot last night. I really loved seeing you wearing my bra. Holy fuck, I've never cum so hard. And that was the first time I've ever squirted!"
Next night, Jennifer had me (voluntarily) wear one of her bras and some panties. The sex was even more unbelievably hotter than the night before. Since then, Jennifer trashed my male PJ's and bought me a couple of baby dolls and matching panties and even some of my own bras. Then she urged me to wear a bra and panties at home during the daytime. The dreams I had become more and more vivid.
Being an estate sales agent, the job allowed me to have a lot of flexible time. I had a late meeting with a client that morning at a 20-acre ranch they wanted to see. Mr. and Mrs. Anderson were a middle aged couple from the Scandinavian area. I think he was Dutch and she was Swedish. She looked the typical, sexy Swedish type. Tall blond about five-ten with blue eyes. She had a shapely body with larger than decent sized boobs (C's? D's?), nice hips and ass. Anyways, Mrs. Anderson called me to set up a time.
Had another one of those dreams, woke up in a sweat and a panty filled with cum, I needed a shower. When I returned, hanging on the closet door was the suit and white shirt I planned to wear but on the bed was a cream coloured camisole and panty set. I looked at Jennifer who smiled back at me. "I think it would be sexy for you to wear under your suit."
I didn't protest the idea but was concerned. Even though it would be beneath my male clothes, the thought of wearing it in public was scary.
"I think your mind thinks it's a great idea." She said to me. I returned a puzzled look. "That hard cock of yours wants to too! Just try it on."
Jenn helped me with the top. I slipped my arms through the loops and let the silky soft material slid over my torso. The top had spaghetti straps with a rose lace trim along the bodice. Then I stepped into the panties. They were shorts with similar lace trim and high open slits on the side. Jennifer chuckled at the tent that protruded out from one of the leg holes
Before I could change my mind, Jennifer pulled over a snug T-shirt and helped me on with my suit that hid any outlines. Regardless of the bulge in my pants, you couldn't tell what I wore underneath.
Driving there, I played with my crotch and rubbed my cock with the panties I wore. I arrived at the site an hour before the clients and took the time to pull out my dick and stroke myself a bit. When I heard the sound of a car pulling in, I quickly hide myself away and tried to cover my tent by buttoning up my jacket.
Rather than Mr. and Mrs., only Mrs. stepped out from the car. The tall blond was dressed neatly in a tight fitted sweater that accentuated her boobs and a cream coloured, mid-thigh length skirt. Even with five inch stilettos, Mrs. Anderson to long, confident strides.
I extended my hand to greet her. Even without her heels, I would have had to look up to her. "Good morning, Mrs. Anderson. No Mr. Anderson?"
"No, he had an emergency meeting at the office and I wanted to take a look at the property." Her blue eyes sparkled as she smiled with her perfectly painted lips. "Mostly just to see the house. We can inspect the rest later. And call me, Annalise"
The house itself was huge with eight en suite bedrooms, a huge living and dining area and a large full gourmet kitchen. In the basement, I showed her the large, temperature controlled wine closet. It was more of a room than a closet. There was a tasting area where I had set up a bottle of fine port that I knew they enjoyed. It was decanted into a crystal container and waited with three fine crystal port glasses.
As we sat next to each other and enjoyed the wine, Annalise asked a number of questions about the house and property. I was getting warm and without thinking, removed my jacket. Then she placed a hand on my knee. It caught me a bit off guard but I didn't want to seem offended or anything. Then her hand climbed higher and higher on my thigh until her palm rested on top of my cock. I grew harder as she squeezed it. "Annalise. Mrs. Anderson, I..."
"Shh!" She squeezed me firmly. "Hans and I have an understanding. He's actually busy with his secretary and the first time we met, I found you very attractive."
She pulled my face to hers and planted a hard, passionate kiss on my lips. Her long tongue probed my mouth. Her fingers took hold of my shirt and before I could do or say anything, she had pulled it over my head. To say she was taken aback was a stretch. Her mouth was agape as she eyed my cami. "Uh..."
"Mrs. Anderson. I can explain." Of course I couldn't. What explanation could I give? "Er... You see... Um..."
She fiddled with my trousers and let them drop around my feet. She stood back to see my matching panties. Then without a word, Annalise stripped off her top and skirt. She wore no bra but a red micro thong that barely covered her pussy. She wrapped her arms around me, her big boobs and nipples pressed into my chest. She kissed me hard. Instantly I was hard.
I dropped to her knees. She grabbed the back of my head and shoved me into her cunt. I started munching through the satin material of her thong. She humped into my face as more and more of her juiced leaked out. Then she spasmed and grunted as she came.
Suddenly she pushed me to the mahogany floor. She pulled my panty waistband down enough to just let my cock pop free. As she squatted, she pulled aside her thong. I slipped deeply inside of her in one shot. She leaned forward and placed both hands on my chest. As she humped up and down, she squeezed my boobs though my camisole.
"Shit! Shit! Shit!" Annalise screamed. "Fu... ck! I'm going to come!"
She pinched my nipples really hard. I instantly started shooting my load inside her unprotected cunt. "Fu... ck...! I'm.... Uh... Uh... Uuuhhh...!"
"Yes! Fuck! Yes!" Annalise continued to pinch my nips. "Fuck! Yes! That's it! Come inside me. Fuck! I can feel you come inside me!"
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