Our Summer Weekend Pt. 03

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.

"Table for Smith," Eric said as I stepped to the garbage can and threw out the garbage before returning and wrapping my arms around him. In public, I still felt a little uneasy and definitely wanted his closeness and protection. He wrapped his arm around me as we were brought to our small table overlooking the bay. I felt like every eye was on me. They had to be watching as I, a crossdresser, with a plug in tried to walk across the room in heels. Of course, they weren't. I am sure some people were looking at me but every time I was in public and someone didn't point or say something, I felt more comfortable.

Eric let me go before holding my seat as I smoothed my dress and sat. I squirmed a bit as I felt the plug move in me. He moved opposite me and sat himself as we were presented with menus and I got a wink before the hostess stepped away.

"You ok?"

"Yes," I whispered, "Just a different feeling. Very erotic"

"Great," he was interrupted by our waiter. We ordered wine and then began to look at the menu. When the waiter returned, we were able to order while he poured. Finally "alone" Eric reached for his glass and I followed.

"I love you Jessica, here's to another great night."

Our glasses clinked and we sipped our whine. Relaxing, we drank and talked while we looked mostly at each other but also at the bay and around the room. There were many couples and some bigger groups at tables. Most were dressed similarly to us in some way. I felt more and more comfortable.

"You are the most beautiful, sexy women here"

"Hardly, but thank you Eric," I said. His words making me feel really good.

Dinner was great. We both order seafood dishes and ate slowly, enjoying each other's company. Tables cleared and were reseated, the waiter checked on us and poured more when, all the normal things that happen at dinner. We finished our wine as we sat talking some more.

"This was so romantic Eric, thank you so much."

"I had a great time Jess and am looking forward to a great night"

The wine had gotten to me and I excused myself before taking my handbag and carefully standing and letting him know I had to use the lady's room. He rose as well like a gentleman and I touched his hand before carefully walking to the bathroom. As, I left the dining area towards the rest room a man, I guess one would say, attractive and around my age let me go in front of him.

"After you miss," he said.

"Thank you," I continued towards the rest rooms. I became aware that the man was following me closely.

As I approached the lady's room a female server, younger and dressed in a black shirt and pants opened the door for me. I glanced back to see the man go into the restroom.

"You ok?" she asked seeing the look on my face.

"Oh yes," relieved to be in the bathroom.

"He was checking you out."

"NOOO," I replied at that surprising statement as we each entered stalls.

"He was and so is every other guy here tonight," she pushed.

I pulled my dress up and my thong down. Sitting on the toilet I was careful of the plug and being tucked as I began to pee.

"What are you talking about? I don't even pass."

"Pass, what does that even mean? Gurl you're exuding femininity and sexuality. Every guy here tonight wants to fuck you and most of the women can't understand why their husband or boyfriend is checking you out as you cross the room."

"Really?"

"When you strut back across the room in your heel and stockings, take note of how many men are looking at you and what their dates are wearing."

Carefully wiping, I stood, pulled my thong back into place and let my dress fall. I exited the stall and washed and dried my hands before checking my makeup.

"Go get him," the server said having washed her hands and leaving the bathroom.

A touch more lipstick made me feel very sexy as I excited the bathroom.

Our eye's met as soon as I came back into the dining area and Eric watched as I crossed the room carefully keeping the plug in me. I did look at some of the other men and they were looking at me. This made me feel great. I wasn't attracted to them though. I realized I wasn't attracted to all men, I was attracted to Eric. It wasn't just physical attraction. It was the fact that he had made me feel so feminine. He had been supportive and accepting and made me feel comfortable. As I approached, Eric rose to seat me and I gave him a peck that everyone saw.

"Thanks. I love you."

I sat down, again smoothing my dress and I gave him a wink as I again felt the plug move in me again. I was getting very horny. He sat down as well. I glanced around the room at other guys and they all knew Eric was going to fuck me tonight.

The waiter reappeared and asked if we wanted dessert. Looking at each other we both wanted to get back to our room at this point.

"No thanks, just pay the check," Eric said as he handed the card to the smiling waiter.

"Eric, don't be so obvious."

"I want you now Jess."

Eric signed the check and rose, taking my hand and helping me stand. He took my hand and led me out of the restaurant. We passed the server who gave me a wink of her own.

"Have fun tonight," she whispered just loud enough for Eric to hear.

He gave a wry smile as we walked to the truck. Always the gentlemen he held the door as I climbed in again feeling that plug as I sat and on every bump and movement of the truck on the way back to the hotel. We made one stop on the way back, at a store to get another bottle of wine. I waited in truck while he went inside quickly. We parked, he got the bag from the store and helped me out and we made our way to our room. It was just 9pm so the only hurry was our own desires.

As we entered the suite, Eric removed his jacket and we met in a kiss.

"Unzip me babe," I said turning and moving my hair to the side very eager to be out of my dress.

"I just need a minute, get comfortable," I said as I stepped towards the bathroom letting the dress fall off my body as I walked in. I knew Eric had gotten glimpse of my lingerie again and was excited to show him everything. I was also pretty sure he would be naked and in bed when I returned.

In the bathroom I removed my thong & the gaffing tape and made sure I was clean. I pulled out the plug and lubed before putting it back in. Finally, I put on my cage so I was his sissy again. Looking in the mirror my makeup still looked good so I brushed my hair out and was ready.

Still wearing the heels, but now just in the torsolette and stockings I stepped into the room.

"Hi," was all I said as he had been watching for me to come out.

Eric, had undressed, turned down the bed, opened the wine and turned down the lights. Soft music was playing from his phone.

"You are so sexy," he said rising as I strutted to him my eyes catching view of his semi hard cock bobbing in front of him.

"Thank you Eric, you always make me feel sexy and feminine," we came together and our lips met in a soft kiss that slowly became deeper. I opened my mouth and let this tongue find mine as my arms went around his neck. Eric's hands went to my ass and he lifted me off the ground. I wrapped my legs around his waist as he stepped towards the bed and he laid me down on it. Breaking our kiss and letting go of each other he rose up as I moved to the center of the bed and laid on my back. Eric came back over me and we met again kissing before he started to descend my body, kissing my neck and shoulders as I moaned.

He moved to my little tits squeezed by the torsolette. He pulled the cups down exposing my nipples and alternating kissing and sucking on them. His mouth on my nipples is one of the most arousing feelings to me. He gives just the right amount of stimulation. Not too soft that it's not noticeable but hard enough that I was writhing all over the bed without being in pain. I held his head to my right nipple at one point and he just nursed on me. If only I could feed him, I thought before he let his teeth graze up from my areola to the tip agonizingly slow.

Rising up on his knees, he held my stockinged legs up in the air by the stilettos and kissed my calves and back of my knees as he admired my anklet.

"This was a surprise," he remarked.

'I like surprising you."

His hands went up my legs again before spreading them and leaning down to kiss the inside of my thighs working from my knees to the bare skin where the stockings ended. As my legs spread, he got to fully see what was his. My clit with a little landing strip above and my pussy with its jewel plug.

I was breathing heavily now I was so horny for him. I knew what I wanted but did not want to say it. Luckily my husband knew what I wanted as well. Though he often likes me to ask him, tonight wasn't for that. As he pushed my thighs back and out, I looked down at him and smiled. Eric eased the plug out of me, leaving it on the bed and then brought his tongue to my pussy and then moved up to my clit. He entered me with two fingers and began flicking his tongue on my clit.

I love watching him go down on me and I tried to prop my body up on my elbows, but the boning of the lingerie made it hard to bend. It also made it hard to take full breathes. Though it had been ok throughout the night now I was definitely needing more air and took quick gasps of air between moans and cries of his name.

Failing to be able to stay up on my elbows, I gave up watching him and fell back on the bed. My hands went to his head and ran through his hair before holding him at my clit. I was shaking my head side to side as the pleasure intensified. I was so worked up that embarrassingly it only took a couple of minutes of this before I cried out.

"Eric, I'm going to CUM."

A little more pressure from him was all it took.

"CUMMING. OH GOD, I CUMMING!" I cried out as I grabbed his head so we stopped moving and held it on my clit. His tongue kept flicking as my little bit of cum oozed out onto it. My back tried to arch, again hard in the torsolette, and my legs shook almost uncontrollably. As my orgasm waned my whole body went limp.

"Come here baby," I said as Eric rose. My arms open I wanted to feel his weight on me.

"Can I be in you now?" he asked before he kissed me. My tongue seeking out any remnants of my cum.

"Of course babe, I want you to make love to me."

"OK, I wasn't sure because you just came."

"I did and it was great but nothing replaces this," I said as I stroked and brought his cock to my pussy.

Opened by his fingers and wet, he slid right into me and kissed me deeply. His cock raked by mt spot already sensitive from before. He pushed fully into as I hugged him close to me, feeling his pubes against me and his full weight press me into the mattress.

"Oh my god, you feel so good Eric"

He held still in me as we kissed more and just felt each other. I was happy to be on my back and let my man make love to me. Eric broke our kiss and then began kissing my neck as he began to move in and out of me. My nipples, still exposed, were being rubbed by his hairy chest getting me even hotter.

"Yes baby," I moaned as he rubbed against my clit. My painted fingernails gripped his back as I also used the stilettos for a bit of grip on the bed to push up my pelvis and meet his thrusts. I was in total bliss as Eric made love to me, his slow thrusts making it last. He didn't need to tell me that he liked being inside me, though I liked when he did. Tonight, other than some soft moans he was relatively quiet. I wasn't quiet and surprisingly as he ground against me, I felt another orgasm building inside me.

"Yes, ERIC!" I exclaimed with each thrust. I continued to hug and pull him to me, wanting us to be one. He alternated between kissing my neck and my lips. His pubes ground harder against me clit in my little cage. His hands rubbed up and down my sides and I would feel them on my bare skin and then though the satin of my tight lingerie. I began to feel like I could cum again.

"I think I'm going to cum again."

"Really? Go for it Jess!"

"I love you, Eric. I love you so much," I cried into his shoulder as I twisted my body to meet him, getting closer.

"Oh god yes."

"Yes, yes, YES!"

As usual the spasms started in my pelvis and spread throughout my body. I inhaled quickly and went silent. I felt my cum leak out of me as the spasms travelled down my legs to my toes and my arms hugged him tightly again. My eyes were closed as my need for oxygen came on.

"OH MY GOOOOOOOOOOOOOOOOOOOODDDDDDDDDDDDDDDDDDDDDDDDDDDD!!!!!!!!!!!!!!!!!" I wailed as I opened my eyes and exhaled before drawing another breathe. My body went totally limp as Eric stopped deep in me. It felt like forever as I spasmed beneath him almost oblivious to anything else.

"Are you ok?"

"Oh my god, I came so hard," I said as he began moving again. I pull his face to mine and we began to make out again. Eric was moving inside me again gently and as we broke our kiss our faces remained close our eyes locked on each other. His thrusts into me were soft and steady but full. He wasn't close yet. I squeezed him with my pussy.

"I love being inside you Jess," he said.

"Baby, you feel so good. It's so big and hard in me"

I looked passed him and lifted my legs in the air, still wearing the heels I watched the anklet swing with his thrusts. This motion also made my hips curl up and allowed him to go even deeper in me.

"OH GOD!" I moaned as his body moved up and he drove his cock up past my second ring. His elbows were above my shoulders giving more leverage to his thrusts into me. I was left with my face in his chest, inhaling his cologne. It was positions like this that made me feel small, dominated and very feminine. Other than a little movement at my waist and squeezing my pussy around his shaft I had very little physical action. Almost all of Eric's torso was grinding and fucking me into the mattress. I was almost being smothered by my big hairy bear and I loved it. I loved being made love to by my husband and now I was ready for his cum.

"Are you going to cum in me again babe?" I mumbled into his chest. His pace of steady long strokes continued into me.

"MMM, Unnnhhhh, Ohhhh, Jess," he was barely discernable but at least got my name right.

He was plowing into me now. I wasn't going to cum again but the feeling deep inside me was very intense. Externally my hands were all over him. From his big shoulders I raked my nails down his back to his butt, squeezing his cheeks and pulling him into me. Up his sides and down his muscular arms that, anchored against my shoulders, pulled him with each thrust. My smooth stocking covered legs wrapped around his powerful hairy ones. I was able to flip my heels off and run my feet up and down his calves, feeling the muscles tense as he pushed with his feet, driving his rod into me.

"I want your cum baby. Give me your cum!"

"Give it to me."

"Cum in me"

"I want your cum,"

"I want your cum."

"I want your cum," I cried over and over as Eric grunted and thrust into me over and over.

And then it happened. His thrusts got sporadic and his grunts louder. With one final push he drove deep into me, pushing me into the bed as I pulled my legs up with my knees bent and squeezed him with my pussy.

"OHHHHHHHHHHHH FUCK, JESSICAAAAAAAAAAAAAAAAAAA!!!"

I felt him pulse into me and then the warmth of his load as it flooded my pussy.

"Yes, give to me."

"Yes, yes, yes, yes, yes, yes." I replied to each of his powerful pulses before they began to wane.

Maybe instinctively my heels gripped the back of his thighs and my arms locked around him keeping him in me. In between little kisses to his chest I thanked him for what he had just given me.

"Thank you, thank you, I love your cum."

Eric bent down and I bent my neck back so we could meet in a deep kiss, before he collapsed his weight fully on me. Thankfully he slid down a bit so I could breathe a bit under his weight and still in tight lingerie. I took his weight fully and rubbed his back gently, his monster cock still in me.

"That's it baby, relax. Thank you. I love you Eric. So full. So good," I rambled in total bliss.

After a few minutes, Eric propped himself up a bit, letting me get some more air. We kissed again.

"Are you ok?" he asked.

"I'm great," I nodded.

"You ready?"

Sadly, I knew he meant to pull out. I opened my legs and my hands moved from his back to his arms. His penis, still semi hard, began to move out of me. His public hair, wet and matted from my cum tickled a bit, his mushroom head raked my prostate one final time as I bit my lip and squeezed as we separated.

Eric sat up on his knees to clear me and reached down to undo my garters from my stockings. I sat up and held the torsolette to my chest as he undid the hooks from the back. Finally able to take a deep breathe again I turned and gave him another peck.

"Thanks. Give me a few minutes,"

I walked towards the bathroom, leaving the torsolette on the dresser. In the bathroom, I removed my anklet and peeled the stockings off. I cleaned my crotch of my cum and sweat but was careful to try and keep Eric's cum in me. Naked I walked back into the bedroom and saw Eric had relaxed on the bed. I grabbed a couple items from the dresser and walked back into the bathroom, knowing he was watching me.

Back in the bathroom the first item was my bely dangle which I put back on before putting on my nighty. I had chosen a royal blue babydoll. It only fastened at the bust so the lower part was a flyaway. I added the g-string panty carefully and then freshened my perfume. As I left the bathroom, I let Eric get a look at me before turning off the main lights so that just the bedside lamps were on. Combined with the TV, which Eric hard turn on, there was enough light in the room. I glanced at the clock on the bedside table as I crossed the room. It was just after 10pm.

"Wow, very sexy Jess. Come here."

I climbed into bed, giving him a kiss before I slid down beside him with my head on his hairy chest and we just relaxed watching some TV and snoozing a bit.

We switched to the news at 11 and watched through the weather, happy to see that tomorrow was going to be another great day. After the sports one of the talk shows came on and we kind of stopped paying attention.

I spoke first.

"I was glad to get back but I kind of wish we had gotten dessert."

Eric jumped up causing me to roll off him and went to the mini fridge. He pulled out cleaned strawberries and a can of whipped cream. That was what else was in the bag from the store. Grabbing the bottle of wine and glasses he beckoned me to follow him onto the balcony. I thought about a robe or something to cover more than the babydoll and then though better of it. He was naked after all.

We sat at the small table and Eric opened the wine and poured two glasses while I opened the strawberries immediately taking one and, pursing my lips, kissed and then took a bite before feeding the rest to him. We picked up our when glasses and made a toast.

"I love you," we both said, definitely not afraid to profess our feelings anymore.

Eric picked up the next strawberry and the can of whipped cream. He put a little too much cream on it before bringing it to my lips and slowly putting it in my mouth. As erotic as I could I took a bite holding it the rest on my lips. Taking the can from him, I reclined and put a dollop on my belly button, placing the rest of the strawberry on it and looking right at Eric. He took the hint and bent between my legs before bending forward and sucking the berry and cream into his mouth and licking me clean.