Our Summer Weekend Pt. 01

This is the next story in the line of Jessica a 40+ CD and her lover 50+ Eric. Although it can be read alone, I suggest you start from the first story in terms of date submitted to get all the details of their relationship. The stories are based on real events with some embellishments and fantasy. Please vote, comment and even e-mail me feedback. Hearing from fans is a great motivator to tell more of our story.

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I scrolled through the web pages to pass the time. Already showered, I had painted my toenails and added press on fingernails. As the polish dried, I was sitting at the desk in panties and a wrap, looking at the plans that we had made for the weekend. I was very excited as we would be spending lots of time together again

In my mind I was going over what I had packed to make sure I had not forgotten anything. No male clothes this time. I was going to be fem when he picked me up. To that end I had made a few adjustments. First being that it was summer and we were going to be in a vacation area I had bought some less formal clothes. Sundresses, skirts and tops. No pants. I was still a CD after all. We had evolved though from my just wearing lingerie or a fancy dress. To fit the role, a lot of shopping had been done. More casual clothes, but also more accessories, jewelry, purses, and shoes. Lots of shoes. Also, realizing I would be in public more, I had bought padded lace bras and small "chicken cutlet" breast enhancers. I still wanted to be me so they weren't a DD cup but they gave me a little more form on top. Along the same lines, we had realized the cage, while fun was not good in public. It had been hard to stay tucked when we played golf and in a swimsuit was ridiculous. Instead, I had researched and found a gaffing tape that would keep me tucked and smooth things out. By doing it correctly I was comfortable and could shower, swim and even still pee without removing it. I still planned on wearing the cage in the bedroom to show Eric I was his sissy wife.

It was 3pm on Friday afternoon. I had taken the afternoon off to be ready to go. Nails dry, I had already shaved my face closely when I hopped into the shower. I started with a good douche and then started shaving. Leaving a nice landing strip over my clit, I removed all traces of hair from my pussy, legs, chest and pits. I let the warm water run over my smooth body as I picked up the loofa and scrubbed myself. Stepping out I dried myself and then was liberal with lotion. As was the norm, I lubed myself. I like to be prepared for his monster. I had already chosen my outfit for the ride up. I had 2 choices in my mind. A suburban housewife or a working wife. I went with the latter and planned on wearing my business suit as if I had just gotten out of work. I had asked Eric to dress in a shirt and tie to match. I donned my wig and brushed it out and applied suitable makeup. I felt very comfortable now applying makeup and dare I say I looked good when I was done.

Stepping out of the bathroom, I went for my lingerie. Tonight, was a lacy purple set. Garterbelt first around my waist and then nude stockings rolled up my smooth legs. I made sure my straps were perfect. Then I tucked and taped myself carefully before pulling on the thong panty. Finally, I hooked the bra around my torso. Before putting my arms through the straps, I inserted the forms and then got everything in place. The pads added a bit of weight on the shoulder straps and as I turned in the mirror, I had a nice profile as they perked up my little titties. Back in the bathroom I add a bit of makeup to my chest to define things a bit more and I put on one of my belly dangles.

Eric was picking me up at 5 and I noticed it was getting close so my blouse was next. It was purple as well and I left 2 buttons undone, it was Friday evening after all. Next came the black pencil skirt, up over my hips, careful of the garters and to tuck my blouse in before I zipped it up. I stepped into my 4" heels before finally putting the blazer on. I looked in the mirror and with the exception of being tall was looking at any businesswoman. I added accessories, a watch, my rings, earrings, necklace and a bracelet. In addition, a new accessory of simple gold anklet.

"You look great," Eric said entering the room and giving me a kiss, "Are these all set?" he continued moving to pick up my bags.

"Yes, and thank you."

As usual I had probably brought too much but I didn't want to be caught unprepared. Eric had one small suitcase and I had two large ones. I followed him down the stairs and into the shop, my heels clicking as I carefully descended. After putting the bags in the backseat, he opened the passenger door to the truck and I climbed up and sat down, smoothing my skirt before swinging my legs in. Eric of course took in the view of my nylon clad legs.

The first part of the drive was pretty uneventful. Traffic was easy as it was after the rush. We chatted about nothing as we drove along. Other than Eric stealing an occasional glance at my nylon covered legs there was nothing unusual. It wasn't until the fuel gauge dropped below a quarter that things started to get interesting.

Eric eased us into a rest stop and pulled up to a pump. As he hopped out, he mentioned he needed to pee before proceeding to start the pump. I then watched as he walked into the building to find the men's room. His mentioning needing to use the bathroom made me realize the same. I had no choice; this was my first test of the weekend. I was both terrified and excited as I sat in the truck. I texted Eric to let him know I was needed to go before taking a deep breath, unbuckled my seatbelt and opened the door. I swung my legs out so my heels found the running boards before stepping down to the pavement.

Another deep breath and I started walking towards the building. It was a catch 22, I wanted to get there fast but the faster I walked the more attention I was afraid I would draw. Instead, I collected myself and corrected my posture and focused on my ladylike walk into the building. This was very exciting for me. As I opened the door to the rest area, I was relieved to find it mostly empty, until I stepped in. My heels clicked with a loud echo through the building and I thought for sure someone would look up and point, laugh or comment. But they didn't. I'm sure one of the handful of people noticed me but they did not care. I found the ladies room and walked in thankful it was empty. I was just a business women / wife using the bathroom. As I finished Eric texted he was waiting. I washed, checked my makeup and exited the restroom.

"Over here Jess," Eric called as I walked out.

We came together and he put his arm around me and we walked out together to the truck. I felt much better now. First, I had done my way inside alone. Now I was with Eric as his wife as we walked back out. He opened the door for me again before climbing in I removed my suit jacket and I settled in as he replaced the fuel hose and got in the truck before we pulled back out onto the highway.

"So?' he asked.

"So...?" I replied.

"How was that?"

"Terrifying and exciting. No one actually seemed to care. I am sure someone will at some point if they pay attention, but I was just another woman."

"Well, you're more than that," he said as he flipped up the center seat of the truck and I slid closer to him. My feet curled up on the seat and I settled in as we cruised down the road. My right hand of course found his crotch and I rubbed him through his pants.

"I have a gift for you," he said

"You do? I like gifts. What is it?"

"I want a BJ first."

I laughed. I guess I had to work for my gift. Although, truth be told, I had been ready to suck his cock since we had gotten back in the truck. I unzipped his pants and pulled out his semi hard cock, stroking it and smiling at him.

"What did you get me?"

"You will see soon, ooooohhhhhhhhh goooooooddddddddddd!!!" he moaned as I bent and my lips parted and I took his cock into my mouth. Eric's hand, that had been around me, rested on the top of my head as I bobbed up and down, stroking him at the same time. He was hard instantly and I relished having his 8" in my mouth as the situation was very exciting. The rest stop had increased my excitement and now I was sucking him as we cruised down the highway passing and being passed by vehicles. I hoped Eric didn't wreck truck. Sucking cock in a vehicle as it drives down the road sounds very erotic. It is, but it's not without issues. As I kneeled on the seat, my head was wedged between his belly and the steering wheel. I couldn't get all of him in my mouth but worked the top with my lips as I jerked him. My skirt had ridden up a bit and if not for the tinted windows a passing driver would have gotten quite a view.

"Yes Jess"

"YES Jess!"

"Yes, YES, YESSSSSS!" he moaned as I bobbed and jerked him faster. I wanted his cum so bad and we both knew I was going to swallow every drop.

"I'm going to cum!" he announced. I made some sounds, my mouth full of his cock.

"JESSICA!" he wailed as he erupted filling my mouth. I immediately started swallowing as he pulsed into my mouth. I pulled off so just his head was in my mouth and I could taste his load as he finished. That salty, sweet, creamy load that I loved going down my throat.

"Now my present!" I giggled as I pulled off him and smiled. His cock cleaned, I put it back in his pants and zipped him up. I took a drink of water and sat back in my seat waiting. Eric laughed, composed himself and then reached behind the seat and pulled out a bag, handing it to me. When I looked inside, I was very surprised.

"A vibrator?" I pulled the pink toy from the bag smiling.

"Yup. It's a good rabbit vibe"

"For me? You want me to use it?

"Yes."

"Now?"

"Yes."

I contemplated his request. Of course, I had masturbated as Jessica before but never in front of him. Logistically my mind also pondered how to accomplish his ask. I started to take my heels off.

"No leave those on but take off your blouse"

I sighed and began unbuttoning my blouse before untucking it and pulling it off.

"Nice," he said see my purple bra.

I laid a towel from the back seat under me and sat back putting one leg on the dash and one behind the driver seat. My tight skirt hampered me and I pulled it up around my waist revealing my stockings, garter belt and panties.

"Very nice!" Eric complimented as he stroked my leg and played with my anklet.

Already very horny, I was hoping the tape would hold. I really wanted his dick in me but my new toy would have to do. As Eric glanced over, I brought it to my lips, kissing it.

"Watch the road," I reminded him before taking it in my mouth to get it nice and wet.

I pulled my thong to the side exposing my pussy. As Eric again looked over, I brought the dildo to my opening and pushed out slightly. My pussy opened and with the lube and steady pressure the rubber penis slid into me. It was no match for him but felt very good as it hit my prostate and filled me. Eric's hand left my ankle and found the buttons turning the toy on. I hadn't paid close attention to how it worked until now.

"Oh Fuck!" I moaned as the shaft moved in and out inside me. The clit vibe also started and being tucked and taped I was able to adjust it a bit and hit the head of my clit.

"Oh shit Eric!" I yelped as my body contorted from the vibrations.

"You like that Jess?"

"It's not your cock but it feels so, fffffffffffffuuuuuuuuuuuuuucccccccccccccccckkkkkkkkkkkkkkk," I trailed off into a cry as Eric snuck his finger in and turned the vibrations up. With my right hand I focused on keeping it deep inside me and on my clit. My left hand came to my chest and I lifted my bra exposing my left breast and I began to kneed it, heightening my excitement. My moans and the buzz of the toy were louder than the noise of the truck going down the road. Eric struggled paying attention to the road, I was happy there weren't many cars on it as he kept looking over at me.

"Fuck." I swore as the vibrations hit my clit and g-spot in time, my body writhing on the seat.

"Fuck, FUCK, FUCK!!!" I was nearing orgasm.

CUUUUUUMMMMMMMIIIIIIIIIIIIIIIIIIIIIIIINNNNNNNNNNNNNNNGGGGGGGGGGGGGGG ERIC!!!" My body convulsed in spasms emanating from my pussy as it clamped down on the toy. My clit, limp and confined, spewed my cum down onto the toy. I was looking right at Eric and his eyes met mine. My orgasms always leave me a little light headed and as I recovered I just rubbed my breasts as Eric stroked my leg again. The vibe was still in me buzzing away. I reached down, turned it off and pulled it out, leaving it on the towel and wiping myself.

"Wow," my head began to clear. I took a sip of water and then began to compose myself. Replacing my thong and bringing my feet down, sitting back up. I wrapped the toy in the towel and put it in the backseat. I pulled my skirt down and then replaced my blouse. It was a struggle to get it tucked in but I soon was able to look in the visor mirror and fix my hair and makeup. As I finished the end of the road neared and that meant our destination was close.

"Almost there Jess."

"I can't wait baby, a weekend in Provincetown." OK so yes, its cliché but real. We had chosen this place on Cape Cod that we felt was "safe" but for other reasons as well. We eased into the hotel parking lot and found a parking space. As I got out of the truck, I smoothed my skirt and blouse before putting by suit jacket back on. Eric got the bags out and he wheeled my two bags towards the door with me taking his smaller bag and my handbag. Ready for our next test we entered the lobby.

"Reservation for Eric Smith," Yes, I did change the last name for the story.

"Yes sir. Here it is, Eric and Jessica Smith," replied the desk clerk typing on the computer, "IDs please."

Eric pulled out his wallet and I removed my license from my handbag nervously handing it to the clerk.

"Thank you, mam," he replied handing it back to me. A little more typing and he took Eric's credit card payment and handed him the room keys while going over the amenities and pointing us to the elevator. Another step cleared I had a new confidence and turned and strutted through the empty lobby to the elevators.

"Feel ok?" Eric pressed the button for our floor and I moved to give him a deep but quick kiss.

"It's working,"

"Of course, Jess. You can be who you want."

The bell dinged for our floor and we walked out of the elevator to our room. Eric slid the key through the reader and opened the door for me to enter first. Bags in, he closed the door behind us and I attacked him. My arms around his neck and my tongue pushing into his mouth.

"I love you so much," I exclaimed, still horny for him.

"I love you, Jessica. We're going to have a great weekend."

Without breaking our kiss, I loosened and removed his tie, undid his belt, button and fly letting his pants fall to the floor. He kicked off his shoes and stepped out of his pants. Breaking our kiss, I stepped back and watched as he removed his shirt, socks and finally his boxers. I love my big bear and now I saw him fully. His manly 240lbs body, his big hair chest and belly, strong hairy legs and his hairiest part, where his magnificent 8' penis was jutting straight out in front of him.

"You want me to leave the heels on?" I asked him as I started to remove my jacket. He nodded yes of course, watching me. I unzipped the skirt and it fell to the floor. Finally, I unbuttoned my blouse and pulled it off. Now in my purple lingerie and stockings I watched as Eric moved to the bed, pulled the covers back and laid down. I grabbed a band from my purse and put my hair in a ponytail before turning to him. Our eyes met an I crawled onto the bed and up to him. We locked in another deep kiss as his hands groped at my ass.

Normally, I love these make out sessions but it was after 11pm and we had a busy day planned for tomorrow. Plus, I had a different foreplay in mind.

"Can we 69?" I asked sitting up.

"Sure baby," I rolled off him and he got up off the bed. Eric grabbed a towel and laid it down as I removed my panties, untaped myself and quickly put my cage on. I also removed the enhancers from my bra and got some lube. I struck a little pose for him as he lay back on the bed, before I pranced over and climbed on top in a 69.

Taking his cock in my mouth, I heard a stifled moan as Eric tongued my pussy before going to work on my clit. Even though he was hard I wanted to get him worked up before I rode him as was my plan tonight. It seemed Eric had another idea first as he pushed two lubed fingers into me and began working my spot.

"Mmmmm, MMMMMMFFFFFFFFFF, MMMMMMM," was all that was heard from either of us. His pressure on my spot didn't take long to achieve his goal. I started to get that dull ache.

"I'm gonna squirt ERIC!" I said before gagging on his cock again.

He doubled down with his fingers inside me as his tongue continued to flick at my caged clit. I was squirming all over him and moaning with my mouth full of his cock. It didn't take much longer and I let go with a high pitch squeal as the liquid flowed out of me spraying across Eric's tongue and face before he took my clit in his mouth. As I continued to squirt, he swallowed as much as he could until it slowed to a dribble. My head came off his cock and laid on his thigh as he withdrew his fingers from me and flicked on my clit again as one hand just rubbed my ass. I stroked him with my hand to keep him hard while I recovered for a minute.

"Oh my god!" I said, "I needed that. I felt like I had to squirt in the truck but didn't want to make a mess."

"I'm going to make you squirt a lot this weekend. Or at least try."

"Bring it on baby!" I took his cock in my mouth again and left a lot of spit on it as I withdrew, rolled off him and turned around. Eric rolled off the towel and wiped his face off, tossing it on the ground before laying back down, his cock sticking straight up out of his hairy pubes.

"I can't wait to get on that," I said as I climbed back on the bed and swung my leg over him. Still in most of my lingerie, stockings and heels, I was ready. I sat on his big belly and smiled down at him before leaning down for a deep kiss. As I did, I reached back with my hand and grabbed his wet cock lining it up with my pussy. He held his hips firm as I sat up a bit, locking eyes again as his cockhead pushed into me. As usual even being worked by the toy and his fingers, my pussy offered a bit of resistance before the expression on my face changed to satisfaction as I slid down on all 8".

I leaned back down and kissed him deeply, our tongues wrestling. Not moving yet, I was just enjoying him filling me. Every time he is inside me, I am still amazed how I can take his monster and how good it feels in me. Eric's arms came around me and I felt his hands on the bare skin of my back as he first played with my bra straps before sliding down to my butt and playing with the garter straps stretched tight over my skin.

Our deep kiss continued as we still had barely moved. I was just squeezing him inside me as his hands came back up and pulled my bra straps off my shoulders. I broke the kiss and sat up on him again. Reaching behind, I undid the bra clasp and let the bra fall away from my chest. Eric's hands were immediately on my little tits and he gentle massaged them. I leaned over his face, wanting him to suckle on me.

"Oh god YES," I moaned as he got my right nipple in his mouth. Slurping sounds came from him as he alternated between my titties. I began to squirm on him a bit as I became more excited. My clit was rubbing on Eric's hairy belly. I pulled my nipple from Eric's mouth and kissed him again.

"You ready babe?" I asked him as I broke the kiss and just leaned over him.