Helping Out Ch. 02

Chapter 2: The Weekend

I woke to the bright morning peaking in from around the dark curtains. I could feel Jenn still breathing deeply, obviously still asleep. The warmth from her body felt good next to my naked skin. As I slowly began to become more aware of my surroundings I noticed that we were in the same position as the previous night, neither of us had moved at all.

I lightly ran my hands up her belly and onto her large breasts, watching with some amusement as goose bumps followed the trail of my fingertips. With the tip of my index finger I circled her nipple, causing it to swell into a delicious looking little bud. Watching her nakedness and feeling her bare skin started to arouse me in spite of my hunger for things other than sex. I was shocked to feel that we had remained joined throughout the entire night.

As I lay there playing with her exposed breasts, I could feel Jenn's body reacting to my touch in other ways. The warm wetness from her crotch started slowly, so slowly that at first I thought it was my imagination, until the moisture on my leg could no longer be mistaken for anything other than what it was.

Jenn had a smile on her face as she slept, I wondered briefly what she was dreaming about. I was determined to try and make her cum while she slept. Reaching down, I gently moved her thick leg over mine while at the same time using the movement to slide a little deeper up inside. The change in position caused her pussy juice to run over my shaved balls, sending a slight thrill up my spine.

I reached down between her legs, feeling her slipperiness on my fingers, loving the feeling. Slowly and softly I teased her clit, watching for signs of her awakening. Her breathing became shallower and faster, but she gave me no sign of awakening. She still lay on my left arm and reaching around I began to play with her nipple. A part of me wanted to get up and kiss her when her gorgeous lips parted in a deep sigh but I resisted the urge.

The wetness on my balls had turned into a flood as my fingers worked their magic. The position I was in didn't allow me to thrust so I steeled myself against my desire and continued to try my best to bring my sister-in-law over the edge.

Jenn's eyes shot wide open as she screamed in ecstasy, her warm cum soaking my legs and her pussy rhythmically clenching my hard member buried deep inside her. Her tight pussy gripping my cock nearly set me off along with her. She arched her back as she came, grinding her big beautiful ass against my pubic hair, sliding my cock even deeper inside her.

Once she had calmed down Jenn tried to roll over but I stopped her.

"Don't. We stayed this way all night. I want to stay this way until I cum too."

Jenn smiled at me, her perfect teeth bright white in the morning light. Pushing back against me she managed to have me roll onto my back while remaining joined to me. She did a little more gymnastics and somehow got her legs underneath her body so that she straddled my waist. I lay back and admired the view as this beautiful woman rode me. Her big ass parted with each downward thrust, giving me the tiniest peaks at her puckered asshole. I could hardly wait until I had the chance to try it out.

Once she shook off the cobwebs Jenn got into a nice and easy rhythm, her tight slick pussy doing its best to milk my seed. I grabbed two handfuls of her large ass and squeezed, her moan of pleasure nearly setting me off again. When she stretched back to ride me, I reached around and felt the full weight of her large breasts. This was finally too much for me and I pulled her down as I thrust up hard into her pussy, grunting out my passion as my cock spurted its own juices deep inside.

Jenn collapsed on top of me and I hugged her tight as my orgasm subsided. We lay together for long minutes in silence, just enjoying the feel of each other as we breathed. Finally Jenn broke the silence saying that she needed to go pee. She sat up and slowly disengaged herself from my cock.

"Freeze Jenn."

She did as she was told and I reached over to the night stand and grabbed my camera. The picture turned out perfect. She was on her hands and knees over my cock, the cheeks of her ass were spread from the position she was in giving me a perfect view of her asshole. The spread lips of her pussy were slightly red and puffy, and her clit was a bright red. But the icing on the cake was the thick glob of cum that had just started to seep from her. I waited until it just started to drip from her swollen clit to snap the picture. The only other way I could have asked for a more erotic picture was to have her gorgeous face in it.

Once I had taken the picture, Jenn got off of me and went into the bathroom. A minute later I heard the toilet flush and the water run in the sink. Jenn came out with a glow on her face that I was sure matched the look on mine.

"You are a dirty boy Jess. You know that?"

"Actually I do. You have no idea just how dirty though Jenn, but you will if you are a good girl."

She laughed, a sound that I had over the years come to love hearing. If I hadn't loved her sister as much as I did, things could have been different between us.

I dragged my lazy ass out of the bed and stood and stretched. Considering the night I had, I felt really good. I pulled Jennifer into my arms and gave her a deep kiss. Her breasts pressed against the top of my stomach and our tongues danced. I broke the kiss with some reluctance and went into the bathroom to do my own thing.

When I came out Jenn was laying on the bed dressed in only a pair of black stockings. She had the TV on and was engrossed in the local news. I could not pay attention, however, as her leg kept swaying, giving me the tiniest of peeks at her shaved pussy. There was something about a woman wearing stockings that had always driven me mad with lust.

I lay down at the end of the bed and began to kiss her toes. Giggling from my kisses, Jennifer told me to stop. Instead of stopping I began to start kissing her ankles, working my way slowly up to her calves. Her giggles turned to low moans as she watched me kiss her legs. She never took her eyes from my face as I slowly kissed my way up her legs, and I tried to keep eye contact with her as well. I stopped my kisses where her stockings ended, barely an inch from her drenched pussy. She had spread her legs for me as I kissed my way up and looked me in the eyes with longing.

"Please Jesse, don't stop. I need it please..."

I grinned up at her as I held her lustful stare. "Sure, on one condition."

"Anything, just, please... lick me."

"This is the time Jenn, I'm going to be in here," I told her as my finger rubbed her pucker asshole.

I saw a flash of fear cross her face, to be quickly replaced with a slight smile and sexual desire.

"Ok, but please, be gentle."

My heart started pounding as I knew I had won. I would be very gentle with her, it was something that I wanted her to enjoy doing immensely.

I gave in to her continued urging by teasing her pussy with a light breath on her moist lips. I laughed as she called me a prick and rewarded her foul mouth with a light flick of my tongue on her swollen nub. The cheeks of her big ass were soaked with her fluids. I ran my tongue lightly up one side of her crotch, avoiding her attempts to have my tongue in her slippery slit.

Teasing her for a few minutes longer I finally gave in and sucked on her red, swollen clit. Her moans guided me, and I tried my best to take her to the very edge before stopping my attentions. I could see her frustration on her face, but at the same time I knew I was going to drive her to an orgasm like she had never had before

As I licked and sucked on her pussy, I started to softly massage her asshole. It was soaked in the juices leaking from her pussy. As the minutes passed I slowly began to insert my finger up inside her ass, at first just the tip before withdrawing, then more and more. Jennifer's panting excited me, the look on her face made me want to jump up and bury myself balls deep in her ass, but I knew to give in would be to ruin everything.

Every so often I would stop licking her pussy and pushing her legs toward her ample chest I would lick lower, slowly penetrating her tight asshole with the tip of my tongue. Soon Jenn had grabbed her legs behind her kneecaps and held them up for me. She was driving me wild, gyrating on my tongue and finger as she was. With a sudden thrust back onto my finger Jennifer impaled herself completely.

Her eyes shot wide open and I could see all the way back into her throat. So a split second I thought she was going to scream in agony, but the scream was accompanied by a gush of fluid in my face as Jennifer came violently. Staying as still as I could, I watched in awe as she quivered just from the sensation of my finger up inside her.

Finally her powerful orgasm subsided and she collapsed on the bed, her whole body shaking as she tried to catch her breath. The whole thing had been too much for me, and I needed release, and soon. I sat up and knelt right below her wide bottom, pushing her legs toward her chest once again. Reaching over to the night stand I took the opened tube of lube and liberally coated my steely prick. Jennifer had recovered enough by this point to help out by holding her legs open for me.

I played with her ass for a bit, slowly sliding one lube coated finger up inside her, then added another with the utmost patience. All I wanted was to do was shove my cock deep up her tiny little hole and bang away until I came, but I knew I had to resist. With my free hand I again played with her swollen clit. Once I had Jenn rocking in beat to my hands I knew it was time.

I was so aroused that the head of my cock had turned purple as I rested it against her greased asshole. Jennifer looked me in the eyes as I started to slowly push and pull back, getting into a nice gentle rhythm. Just the bare tip of my cock pressed into her ass before I pulled out. As time went on, I slowly started going a bit deeper. Ten minutes later I stopped my tease and determinedly but gently started to enter her.

"Oh Jess, that feels so strange."

"Do you want me to stop?"

Jenn shook her head with her eyes closed. "No, It's not a bad feeling, just strange. Just keep going slow..."

Just then Jennifer's eyes went wide as the head of my cock slipped past her ring. Again her mouth opened wide in a scream as she came suddenly, her cum soaking my cock and dripping from my balls. In the throes of passion, Jennifer thrust down onto me and when she was finished I could feel that I was deep inside her.

I stayed still inside her, looking down into her half-slitted eyes as Jennifer slowly came back down from her orgasm. She looked so hot as her chest heaved with her breathing, her eyes filled with lust. It was as if each orgasm she had drove her to want more. I reached down and began to massage her large breasts, teasing her nipples as I slowly withdrew from her tiny hole. Jennifer bit her lip as my cock started to slide back up inside her, but from the way she pushed back onto me I didn't think she did it from pain. Her smooth-shaven pussy was soaked, as it ran down it helped to keep us lubricated while I fucked her ass.

Watching her tight ass grip my swollen dick was nearly more than I could stand. Jennifer still had a hold of her legs and as the minutes passed I slowly picked up my pace. In minutes I was pumping away with a good rhythm, my heavy balls slapping against Jenn's big ass cheeks. Jennifer's breathing had picked up again as we fucked, both of us silent except for our heavy breathing. I looked up from watching myself penetrate my sister-in-laws asshole to look into Jennifer's eyes.

She was watching my eyes with a wide smile on her face and ran her tongue suggestively over her lips before she spoke.

"I want to feel you cum in my ass Jess. It feels so good, just as you promised. Cum in me please..."

Listening to her beg for my cum in her ass was too much and I drove deep as my cock twitched deep inside her ass. My orgasm seemed to be stretched out almost unnaturally as I grunted as I shook with pleasure. All the while as I came, Jenn was talking, telling me to fill her ass up. Finally I collapsed on top of her, my cock still inside, my face pressed against Jenn's warm breasts. After a moment I lifted my head and kissed her tenderly on the lips. I think the kissed shocked both of us, and the looks on each other's faces had us laughing in seconds.

"Get up Jess. I need to go to the bathroom."

"Get me my camera first Jennifer. I want to get a pic of this. You look too good with my dick in your ass to trust just to memory."

She grinned up at me and reached over for the camera. I sat back up and Jenn spread her thick legs apart as far as she could. She smiled at the camera as I focussed on her. Her pussy was still soaked, and my cock hadn't lost its hardness yet. I asked her to push in her arms a bit, causing her thirty-eight D's to mash together a bit. I pulled my cock back just a little and snapped the pic as her asshole gripped me and was pulled along a bit. Then I slowly pulled completely out and waited until my cum just started to leak from her newly stretched hole. I took another picture then, and another after my cum had just started to run down the crease between her large buttocks.

Jenn got up and went into the bathroom once again, and I watched her as her big ass flexed and swayed as she walked. I could smell the scent of our lust in the room, but even that was unable to revive my desire. At that moment all I could think about was food.

I suggested that we leave the room and head out to a little restaurant not far from the hotel we were staying at, and Jennifer readily agreed. She searched through her bag and pulling out her clothes, started to get dressed. I watched her pull on her G-string as I dressed, and smiled as she slipped on a short skirt and a white blouse. She kept the stockings on as she slipped on a pair of black high heels. I looked underdressed next to her in a pair of jeans and a denim shirt. Jennifer grabbed her makeup bag and five minutes later exited the bathroom looking as gorgeous as always.

At breakfast we talked about how we would spend the rest of the day, and Jenn confided in me that so far the weekend had exceeded her expectations.

"I had started putting a little bit of money off to the side the moment I knew it was going to happen Jesse, just in case things worked out between us, and I was wondering if you would like to go out for dinner with me tonight."

"Won't we risk running into Nathan?"

"No. I asked him to stay in his room this weekend, in case I needed to call him for support. He'll be in his room. He brought some work up with him, and will spend the weekend catching up. We don't have to worry about that."

"Well, if you think its ok, I'm game."

Jennifer smiled at me. "I'm glad. Before we go, I want to go shopping with you."

Jennifer must have noticed my eyes rolling in my head as she quickly elaborated. "You'll like this kind of shopping. I want to spend some money buying an outfit I can wear for you. Especially things to wear under it."

I tried to hold it back, but it was hopeless, and I felt a wide grin stretch across my face. I paid for our late breakfast and we left the restaurant, walking back to the hotel to get in my car. I drove to the mall and we spent several hours in various shops, Jenn picking out a lot of sexy outfits and trying them on for me before I finally picked the one I liked the best. Then we left the mall and drove downtown to a lingerie shop. Another hour and a half later we left with Jennifer's purchases and drove back to the hotel.

We had several more hours to kill before we would be leaving for dinner so when Jennifer suggested that we have a nap, I was more than willing. We both stripped off our clothing and lay down beside each other. Spooning beside each other I could feel the warmth of Jenn's body, the smooth skin of her back pressed against my chest and stomach, her ass against my crotch and her thick thighs next to my legs.

Just as consciousness started to leave me, I felt Jennifer arch her back a bit and then rub her ass back down me. In spite of our earlier exertions, my body reacted swiftly. Soon my fully engorged cock was being rubbed between her large ass cheeks. I played with her soft belly as I moved closer and started to kiss the back of her neck. Jennifer moaned as I trailed my kisses up and over to the side of her neck, up to her ear.

I sucked on her ear as Jennifer giggled beside me, squirming under my hand. I reached up to her ample chest and began kneading her large breasts. Her giggles turned to low moans as I worked my large hands into her flesh. I broke my hold just long enough to put Jennifer onto her back and I lay down between her spread legs.

We kissed each other slowly and with feeling, I could feel Jennifer's heat and wetness from her womanhood on my erect cock. With a slight movement I was inside her. Our kisses deepened as we slowly fucked. I pulled back and held myself up on my hands as I rhythmically thrust deep inside my sister-in-law. Her eyes were half closed as she whispered to me to fuck her.

Resisting the urge to bang away, I continued my slow and easy fuck, bending down once in a while to kiss my beautiful sister-in-law. Her pussy was so wet that my ball sack was absolutely soaked with her juices. The smell of our sex was driving me wild. I bent down and took on of Jenn's nipples into my mouth and nipped it slightly.

Jenn's eyes shot wide open and she grabbed my ass, pulling me deep inside her. She had a wicked grin on her face as she looked up at me.

"Do that again Jess, and I'll be yours forever..."

Smiling down at her, I bent back down and teased her with my tongue circling her nipples, first one slowly, then the other. Jenn's breathing quickened as I teased her and her pussy got even wetter. I could feel her juices dripping from my heavy balls. I alternated between nipples, first sucking one and then the other into my mouth while teasing it with my tongue.

Jenn tightened her grip on my ass cheeks and begged me to bite her nipple. When I knew she was lost to herself I bit down hard. I was hardly prepared for her reaction.

She pulled so hard on my ass that I felt I was melting into her most sacred of places. Her mouth shot wide open and the scream I expected to pierce the air never materialized. She just lay there shaking in ecstasy, and her whole body shook with her powerful orgasm, her pussy convulsing around my cock. The sensation of her pussy gripping and releasing me so quickly set me off, I shuddered as my cock spurted deep inside Jennifer's sopping wet hole. I collapsed on top of her breathing hard.

Jennifer released my ass and ran her arms up and down my back while I lay on top of her, my head nestled between her gorgeous breasts. Slowly my breathing returned to normal and I sat up a bit and looked down at Jenn. Her hair was dishevelled and her gorgeous brown eyes sparkled. I smiled at her beauty and bent down to kiss her gently. I rolled off of her and pulled her close, snuggling my arm between her heavy breasts.

* **

When I awoke a couple hours later, the bed was empty next to me. I noticed the bathroom door was closed and I could hear noises within. Stretching lazily, I waited in the warm and comfortable bed. Several minutes later Jennifer came out of the bathroom all dressed up for our secret night on the town.

She had just gotten out of the shower, and her thick dark hair was still slightly wet. She had put on makeup lightly, just the way I loved it. Jenn wore the clothing we had picked out earlier in the day, but I could only imagine which of the outfits she had on underneath.