My Dilemma

My name is Vanessa. I am 30 years old, standing 5'7" tall and a nice pair of DD breast, which I believed were my best feature.

I met this guy, Jason, at a friend's birthday party and we clicked immediately. After that night, we spoke for hours at a time and sent each other naughty pictures. It took just over a week for Jason to invite me to his house, and I accepted without hesitation. Little did I know, that visiting his house was going to mess up my life.

I got to Jason's house and he introduced me to his dad. His dad was tall, muscular and from what I could tell, cool. He was playing a video game and barely acknowledged my presence. I went into Jason's room and we fucked twice that evening. I was conscious that his dad was right outside, so I tried to be as quiet as possible.

My troubles began the first night I slept at Jason. We had just finished having sex when I got up to go to the bathroom. As I was approaching the bathroom, Jason's dad came out of the bathroom, naked. My eyes opened wide. I could not believe the size of his dick and it was soft.

He made no attempt to cover up and just walked past me back to his bedroom. I sat on the toilet after I had a pee. My pussy was twitching like crazy.

"Now I see where Jason got it from," I thought.

From that night, I began to see Jason's dad in a different light. One night he had a friend over and that poor woman was grunting and screaming for about two hours.

"Is your dad going to kill that woman?" I asked Jason.

"She keeps coming back so she must like it," he replied, smiling.

Hearing that woman enjoying the fucking she was getting, made my dilemma worse. I wanted what she was getting. Jason fucked well but lacked the stamina and the size of his father. I was crossing into dangerous waters, as my pussy began to lead my thought process.

I found myself thinking of his dad and wondering what he would do if I turned up and Jason wasn't home. I got the answer to that question a few months later when Jason went to the USA to visit friends of the family.

I went over to help Jason pack. His dad's friend was over getting a pounding that had my pussy on fire. It seemed like the fucking was on a another level. She was now narrating everything he did, and my pussy was reacting to everything I was hearing. However, what made up my mind came just as we had finished packing.

"Robert no. Not my ass," she cried.

What followed that plea was a combination of swearing and screaming, each time she came. I was riding Jason hard when Robert's friend began to growl and then scream.

"CUMMING!" she shouted and then there was silence.

Jason and I were giggling when I heard his dad go into the kitchen. I was still riding Jason but I was thinking about his dad. Jason came shortly after that and I offered to get us a drink. I put on one of Jason's shorts and a T-shirt.

Jason's Dad was watching the TV while he ate a snack.

"Hi, Robert. How are you?" I asked.

"I'm fine. How are you?" he replied.

"I'm good," I said, swooning a bit as I said it.

Robert didn't look up from his plate while I answered but I know, he made a mental note of the way I answered.

Later that night, I heard his friend grunting and groaning as Robert pounded her again.

"How old is your dad?" I asked Jason.

"65," he replied.

"Wow!" I said. "He neither looks nor behaves that old."

I kissed Jason and began to caress his body in order to mask what my body was going through thinking about his dad. I fucked Jason in positions I imagined his dad was putting the lady in. On a few occasions, I had to stop Jason from cumming to extend my pleasure. When I finally allowed him to cum, it coincided with my own orgasm, which followed Robert's lady friend screaming.

The following week, I told my manager that I had a delivery arriving on Wednesday, so I'd take it as a holiday. She agreed and my pussy began twitching like mad. The reason I asked for Wednesday was to visit Robert, who was off on Wednesdays.

I woke Wednesday morning and began getting ready to go over to Robert. Using the information Jason gave me, I estimated what time his dad got back from the gym. It seemed like my lucky stars were aligned. As I approached the road to their house, Robert appeared in front of me, on his way home from the gym.

"Hi, Vanessa. This is a surprise," Robert said in a deep voice, smiling sweetly. "What are you doing over this side?" he asked.

"Hi Robert. I took some stuff for my grandparents who live nearby and decided to come and see how you are," I replied. Robert looked at me, still smiling but with a knowing expression on his face.

As we walked together, I saw my reflection in a window and saw that my nipples were hard. I'm sure Robert saw them as well. Inside, Robert took out some meat to cook as we chatted and it was then that my opportunity presented itself.

"Let me marinate the meat while you take a shower," I said, opening the condiment cupboard.

"Are you sure?" he quizzed.

"Of course," I replied, trying to remain calm.

Robert went into the shower. I marinated the meat, washed my hands, shed my clothes and walked towards the shower. The door was ajar and as I pushed the door and stepped in, Robert pulled back the shower curtain and motioned for me to step in.

Robert pulled me into his amazing body and kissed me softly. That kiss was the master switch for my body. I was already in a heightened state of arousal but that kiss put my nervous system on red alert. Robert put some body wash on a cloth and began to bathe me. I was hissing and oooooh-ing as he gently moved the cloth around my body. As he came up my inside leg, I reached out and held his hardening dick. When he touched my pussy and pulled the cloth across my clit, I grabbed him.

"Oh, oh oh, cumming," I said in a squeaky voice before my pussy erupted.

That was my first experience of an orgasm like that. Almost no build up. Just a very rapid intensification followed by an explosive type release. My body was shaking with the most powerful orgasm someone had ever given me.

Robert rinsed my body, taking his time to remove every bit of soap. The gentle pressure of the water served to turn me on even more. We dried each other and moved to the bedroom.

Robert gently laid me on the bed and began suck my nipples. He was gently squeezing one breast as he sucked the nipple of the other. It was during this foreplay that realised I liked a little pain.

Robert nipped my nipple with his teeth. I grabbed his neck and hissed "Do that again."

He did it again to that nipple and the same to the other nipple. I was so turned on, I felt my juices leaking out of my pussy.

Robert began to nibble his way down my body. I was squirming with each nibble he place on my belly. With all of the sex I had had up to that day, I never experienced these types of sensations. When Robert got to my pussy, he paused.

"You have a lovely, fat pussy," he said.

I looked down at his bald head, and the beads of water on his muscular arms and shoulders and my pussy twitched violently. Much in the same way he had pulled the cloth over my clit in the shower, he did the same thing now with his tongue. My hips flew up off the bed.

"OH, MY GOD!" I shouted.

When he sucked my clit into his mouth, I went delirious. I slapped and grabbed his head with both hands, increasing the pressure and came so hard.

"OH FUCK!" was all I could say. The eruption that occurred in my pussy made my entire body shake. What made it worse was through all the abuse to his head, Robert continued to flick my clit hard. I came again and again. I tried to get away but he easily held me in place. I came so much that I had tears in my eyes.

Robert released my clit and slowly made his way back up my body. With his face hovering just above mine, he looked into my eyes.

"Are you alright?" he asked in a deep voice.

"That was the first time I had my pussy eaten so well. Boys have tasted it but were more interested in fucking me," I said in between the gasps for air.

Robert kissed me softly. For the first time, I tasted my pussy juices, a taste that I really enjoyed. I wrapped my arms around his neck and kissed him back, licking all of my juices from around his mouth. Suddenly, I felt my pussy stretch. His aim was perfect and as he slowly pushed his dick further into my pussy, I got louder and louder.

"JESUS CHRIST!" I shouted as his dick opened my pussy wide.

His dick touched a place deep in my pussy that caused a little pain and I stopped him. He didn't pull it out but he stopped moving for a bit. As the pain went away, I began to move my hips, signalling him to continue going deeper. He pulled his dick all the way out and showed me. His dick was shining with my juices. It was then I realised how big his dick was. There was still another couple of inches of his dick that was still dry, and his dick had already touched places never before touched.

Robert pushed his dick back into me, balls deep. I screamed. Robert pushed my knees to my chest and went balls deep again. This time, he began to fuck me. I was swearing as I thrashed about. I had never been in that position and each time I came, I slapped him and bit him.

Through each orgasm, Robert fucked my pussy harder. I was coming again when he pulled his dick completely out and let me go. The resulting orgasm was so powerful that I was literally bouncing around his bed. With no dick in place, my pussy was clamping violently and seemed to go on forever.

While I was rolling around on his bed, Robert grabbed my hips and pulled me to the edge of the bed. He placed me on my all fours and guided his massive dick deep into my pussy again.

"Robert, Robert, Robert," I kept repeating as I repeatedly slapped the bed.

His strokes were slow and long. He pushed his dick all the way in and then pulled it back to the tip. That slow movement excited every nerve in my pussy. I couldn't believe how quickly I came. I had become accustomed to the frantic fucking guys my age gave. This fucking was on an entirely new level.

"OH FUCK, CUMMING!" I shouted for the umpteenth time.

Robert continued to fuck me, but with an increased pace. I was finding it hard to get enough air into my system to keep up the adrenaline each orgasm produced.

"Robert, can I have some water?" I said as I gasped for air.

Robert brought me some water. As I drank, I looked at his dick. It was so big and hard, throbbing to the beat of his heart.

"Can I rest a bit? I asked. "I have never been fucked like this before."

"No problem," he said in a deep voice.

He lay on his back and I snuggled up to him, resting my head on his chest. I was so tired from cumming so much that it didn't take long for me to fall asleep.

I woke to see Robert in the same position, asleep. His gentle breathing almost seemed too calm for such a big man. As I looked down his body, my eyes focused on his dick. I studied it for a bit, watching how it lay across his left hip and marvelling at its size. I gently slid down his body, lifted his dick and wrapped my lips around its head. I swirled my tongue around the ridge of the head and savoured the taste of my juices.

In less than a minute, his dick began to respond. As it got harder, it became increasingly more difficult to suck more than about five inches of his dick. I sucked what I could and kept my movement smooth, making sure to pull my lips past the ridge every time.

"Hmmmm, that feels so nice," Robert said as I sucked his dick.

I looked up and he was smiling. He began to caress the back of my neck and across my shoulders, a feeling that added to my heightened state of horniness.

"Oh my god, that feels so good," I said, still stroking his dick.

After about five minutes of sucking his dick, Robert slipped a thick finger into my pussy. I moaned loudly and wriggled my hips. However, when he pulled it out and pushed it into my ass, I growled and shouted.

"OH, MY GOD!" I shouted as I sprang up, arching my back.

Robert began to finger fuck my ass. He squirted some lube onto his finger and began to finger fuck me faster. I was now fucking his finger. When he reached between my legs and rubbed my clit, I came so hard. Once again my pussy was clamping violently with nothing to grab on to.

I was still cumming when Robert got up and pulled me onto my all fours. I heard him squirt the lube on his dick and waited for the pain. He pressed the head against my butthole until it slipped in. In response to the intense stretching, I screamed and begged him to go slow. Robert pushed his dick further up my ass slowly. When he was eventually balls deep in my ass, he held it there. He began to gently rock from side to side, a movement that helped me to get accustomed to the monster up my ass. When I began to slowly fuck his dick, he began to fuck my ass.

I remember his friend crying when he fucked her ass and it quickly became clear as to why. Robert's style of ass fucking was like nothing I have felt or seen. He used his long, thick dick to push me to the edge of consciousness. His strokes were long and powerful. Each time he pulled out to the tip and drove it back in, I groaned. If I thought I liked anal sex before, I loved it after this session.

My orgasms came in waves that seemed to be getting closer and closer. Each time I came, I seemed to be drifting towards unconsciousness, like I was on a natural high. What seemed like a distant sound was Robert growling as he picked up the pace. My body had just erupted in another massive orgasm when I heard Robert announce he was cumming. He slammed his dick balls deep up my ass and I felt his cum hitting my insides.

Robert curled me into the fetal position and wrapped himself around me. We remained like that until his dick was soft and I pushed it out.

I woke alone in the bedroom. Robert was relaxing on the sofa watching the TV, naked. I snuggled up to him and inhaled the pheromones from his armpit.

"You are so fucking sexy," I said after another whiff of pheromones.

"So are you," he said.

"That fucking has left me with a dilemma. I like Jason a lot but he fucks nothing like you," I continued.

He said that he would stay in his room whenever I came over. That would stop us from taking sneaky peeks at each other.

Fast forward six months and Jason and I had broken up. I wanted us to move in together and he didn't want to. We had several arguments about it and eventually decided to go out separate ways. A week after we broke up, Robert was fucking me better than he had before and every time we fucked after that, he took me to another level.

At first, my dilemma was fucking my boyfriend's dad. Now my dilemma was that I wanted Robert's dick all the time.