Help Me Cum

My story begins during that one fateful trip my aunt made to visit my mom and I. I was 19 at the time and my mom and I lived alone in our condo overlooking the water. Our house was nice, a big pool and a hot tub downstairs (my mom had a great job and that left us very well off). I also had a problem. After many years of masturbation I could not make myself reach an orgasm. I thought I came close a couple of times, but the fact that it never happened to me was cause for worry and I began noticing my cock would begin to hurt as it stayed up for hours on end at some times. My 21 year old girlfriend was not the type to give, so I was still a virgin, but I had managed to get my hands on her beautiful tits a couple of times when she felt really horny.

I was sitting in my room thinking about those tits when I noticed my mom walking from the bathroom into her room which was just across from mine in some very skimpy underwear. The women in my family are all very busty and the white, thin laced bra exaggerated her curves very nicely. But she was of course my mom and I knew thinking and looking at her in that way was wrong so I tried to avert my eyes but I had trouble as she dressed slowly (almost as if she noticed me watching) and my tool began to grow. Obviously she was not looking at me the way I was, and I felt ashamed as I got up and closed my bedroom door.

Just then the phone rang and I was greeted with the sweet voice of my girlfriend.

“Hi babe, I was just thinking about you and I was hoping you could come over and help me out with something.”

She sounded strange but very enticing, unfortunately my mom and I were going to pick up my aunt from the airport so I couldn’t go over there no matter how curious I found myself becoming.

“Well all right, maybe tomorrow I could come over and meet your aunt?”

“Sure” I said, “Show up around 4 ok?”

“Sounds good babe.”

She hung up and I went downstairs and noticed my mom’s blouse was showing a little more cleavage than usual, but I quickly looked outside to avoid getting a raging hard-on right there.

“Well we better get going” my mom said, and as she led the way I noticed how shapely her ass looked in her jeans. I’m one lucky guy, I thought to myself.

The ride to the airport was boring and uneventful as my mom discussed her excitement over the arrival of her favorite sister.

When she got off the plane and headed towards us I noticed how incredibly hot she looked for a woman of 30. She had short red hair and her t-shirt held back the most amazing tits I’d ever seen covered before. She ran over and hugged my mom which I found oddly arousing and then moved over to me and held me close for a considerable amount of time. I looked down and noticed her nice chest was also accompanied by a shapely ass and a moderately slim waist. It was amazing to see a women like this in a magazine but here she was in my arms!

Oh Shit! I just noticed a slight bulge in my pants from all this exploring. I hope she didn’t realize it! My worries seemed put to rest as she just let me go with a smile but I have to admit that her nipples seemed to poke out of her shirt a little, but that was most likely my imagination.

I sat in the back with my aunt as my mom drove towards home and talked endlessly about all the hard work I’d done in school and how far I was going in life.

“Well you have quite a boy here!” my aunt exclaimed as she patted my leg, a little too close to my lap for me to ignore.

“A success in many areas I would imagine” She smiled and to my amazement slid her hand along my crotch before quickly removing it and smiling. I must have dreamt what just happened. Things like this are only found in xxx movies I thought to myself! My aunt would never hit on me like that. But the experience left me aroused despite my logic and I turned to see my aunt blushing and catching quick glimpses of me through the corner of her eye which turned my cheeks a deep pink.

“Are you all right honey?” my mom asked looking at me in her mirror.

“Yeah mom, just a little hot”

“I’d say more than a little” my aunt whispered, which did nothing for my situation but she simply turned and looked out the window.

The next day my mom and aunt headed into town to do some shopping and my girlfriend showed up a few minutes before 4 wearing the tightest pair of jeans I’d ever seen on her and a small top which pushed up her C-cup breasts to perfection. She was definitely not the busty aunt which filled my dreams the previous night but her sexiness was of a different kind. Those abs and her cute little behind were her greatest assets.

She walked into the house giving me a kiss, “hey sweetie, so where’s your mom and aunt?”

“Oh, they left to shop for a few hours, but if you hang around for dinner you could still meet her.”

She moved slowly across the room, looking a little nervous and I knew there was something on her mind, “Let’s go upstairs to your room” she said as coolly as she could and I was beginning to wonder what exactly she had come over for.

When we got to my room she sat on my bed and crossed her legs still looking nervous but gaining more confidence as she saw the wonder in my eyes.

“Look, we’ve been going out for a year now and I’ve been so selfish by closing my body off to you the way I have. I can’t take it anymore sweetie, so I want us to get must closer...”

She got off the bed and walked toward me pressing her hips to mine and taking my finger into her hands and placing it in her wet mouth. She closed her eyes and sucked it slowly as my eyes just got wider and my dick pressed into her groin. She finally released my finger and I looked into her eyes, seeing a lust I’d never noticed before. I knew exactly what she wanted.

I let my hands wander to her ass, rubbing it and grabbing the jean covered flesh as I pushed my manhood into her pelvis watching the excitement grow in her eyes as it grew against her. She then removed her top with one perfect movement and I was right up against her bra covered breasts. The sheer black lace of the bra pressed into me and I quickly moved my hands up to cup her tits while she placed her hand on my cock and began massaging it through my pants. She moaned as her nipples became alive under my touch and begged to be released into the cool air. I moved my hands to her back and undid the clasp, slowly moving the straps over her creamy shoulders until finally her naked tits were exposed to me. Our lips locked as we massaged each other with growing eagerness.

Then she took a step back, breathing heavily as her beautiful body rose and fell. She slowly undid the button on her jeans and slid them down revealing a naked and neatly trimmed pussy. She smiled weakly and gasped as I removed my clothes and revealed my overly enlarged tool. My inability to cum had obviously added a few inches to my penis which stretched out forward toward my naked girlfriend.

I saw only hunger in her eyes as she approached me and touched it with a cautious finger, running it from the head down to my balls. Soon she had her entire hand around it, exploring the veins and jerking it up and down a couple slow times. Her soft skin was making me unbearably honry and I just wanted to jump her right there.

“Oh baby... I don’t want to tease you, so please just fuck me.”

I had never heard her say fuck in my entire life! And here she was begging me to enter her virgin pussy. She lay down on the bed and opened her legs to reveal the deep wetness which lay between and started moving her hands all over her body, cupping her tits and beginning to moan in anticipation.

I moved my cock to her pussy lips and moved it around, trying to find all the spots I’d heard about in my porn tapes. Her body shivered as I slowly played with her.

“mmmm.... Please fuck me baby... don’t tease me....”

I needed no more encouragement as I began to press into her wetness and found her increasing tightness incredibly arousing. It got so tight and I began to worry that I was hurting her but she grabbed me and pulled me further in, leaving about an inch out of her pussy. She moaned as she pulled my lips to hers and began humping against my still growing manhood. I had never been this aroused in my life and I couldn’t believe I was still getting bigger! She lay in complete ecstasy, screaming and moaning as I quickened my pace and brought her closer to the edge. I sucked her nipples into my mouth and ran my hands all over her sweaty body. I felt so close to cumming, and I knew I could do it if only she could keep this up but just then she screamed and pulled me all the way inside her as her pussy muscles clamped down on my rod. It felt so good but she stopped moving and just held me inside her which was stopping my soon to come orgasm.

“Oh that was so good baby, but please pull out. I don’t think I can take your size anymore” I complied and was left unsatisfied. As she dressed my cock began to shrink and so I simply put my clothes back on still feeling incredibly horny but she wasn’t in the mood for any more.

She left then, but not before passionately kissing me and rubbing my thick cock one more time which only made me want to get back to that sweet pussy right away. I looked around my room and wondered why I should be cursed to please a woman like that but not receive my reward.

“That was quite the show”

MY AUNT! I couldn’t believe it! She was standing in my mom’s room with a cam-corder and must have seen most or all of the entire experience! I had left the door open and must have been too caught up to hear them come back.

“Oh don’t worry, your mom is still out shopping, but I needed to get back to use the washroom. What a surprise to find you like that!”

I was beat red, “I’m so sorry auntie, but why did you film me?”

“Oh well, I have my reasons. I think we need to focus on your problem. I’ve seen men cum like there’s no tomorrow during such hot sex but you never even got any precum out of that did you?”

“Well... no...” I said still very embarrassed but a little turned on by all of this.

“Well then, I think we better get you to a doctor tomorrow, so we can figure this out. And don’t worry, we can leave your mom out of this... for now”

As she left I felt a strange sense of longing for her. And even though I had just had sex, my mind drifted to her busty tits and the thought of what she would be like to fuck. But I couldn’t think that way, and with a girlfriend who now wanted me I could get all the action I wanted. I just hope that doctor can help me finally reach an orgasm.

As I drifted off to sleep that night after eating supper with my mom and aunt I still couldn’t get her out of my thoughts. And I also discovered my mom crept in as well and filled my fantasies with a new body. I could only wonder what tomorrow will bring.

The next morning I woke to the sound of a shower running and my mom’s door open just a crack. I realized it was my aunt in the shower and so against my better judgment, I slowly sneaked over to the crack in my mother’s door and took a look inside. There she was, with her back to me and completely naked. Her ass was just as beautiful as I had imagined and I was immediately hard as a rock. I felt my cautiousness drift away as I stood there watching her. If only she would turn around and give me a quick look at those tits.

“I guess I’m not the only one around here with a voyeuristic side!”

I whipped around to see my aunt, wrapped in a towel with her skin still wet from her shower. I had a great view of some amazing wet cleavage and her breathing was increasing as her face grew to a nice shade of red. I could not pull my eyes away from her rising and falling, wet breasts not matter how hard I tried.

“Well at least we know it can stand up without any problems” she said, slowly walking away after glancing down at my raging hard-on grinning from ear to ear. As I watched her ass sway back and forth all I could think of was touching her.

I went back to my room with the intention of finally cumming but I was only left in pain as I could not bring myself to orgasm even with the thought of my mom’s naked ass and my aunt’s beautiful wet cleavage to help me.

I hit the shower and managed to calm down as I headed downstairs to eat breakfast. During the meal I glanced from woman to woman feeling such a lust and wanting nothing less than to fuck them hour after hour. My inhibitions were gone now and all that remained was the strongest sexual feelings I’ve ever had. My aunt seemed to exaggerate her movements, leaning over the table allowing her tits to hang down and tease me and I nearly had to masturbate right there when my mom bent over to get something from the fridge and her panties became exposed. My aunt could only grin, as she fully understood what I was thinking.

My mom had to go to work that day so my aunt and I saw her off at the door and she then informed me that we had a doctor’s appointment to go to right away. We locked up the house and headed to the car where she let me in my door and seemingly by accident rubbed her right tit against my arm. The feeling was absolutely electric.

During the drive to the clinic I was still feeling horny and without thinking I placed my hand on my aunt’s exposed leg. She only smiled and kept driving as I rubbed her soft flesh and wondered if I should go any further. It seemed stupid to hide my feelings from her, now that she knew my sexual fantasies. Unfortunately before I could work up the courage we arrived and I had to take a few minutes to regain my composure.

As we entered I noticed the waiting room was all but empty and after checking in we took a seat in some chairs near the far end. My aunt moved her chair purposely closer to mine and pretended to be very interested in a magazine I had picked up as she pressed her breasts into my arm. My mind was going in a million different directions. I tried looking around the room to keep myself under control but all my eyes found was the incredibly sexy female doctor who was looking over some form behind the reception desk. Her uniform was tight and she had curves in all the right places. Her blonde hair fell about shoulder length and her tits were nice and perky under her blouse. Her skirt ended just above her knees which was disappointing but from there down her legs looked slender and smooth.

“Do you think she’s better looking than me?” My aunt said with a devilish look in her eye.

“She’s good looking, but you’re one of the hottest women I’ve ever laid my eyes on auntie.”

“Thanks! I’m glad we’re on the same page” She whispered as she runs her hand quickly over my cock for the second time since she came and I think this time I heard the slightest moan come from her sweet lips.

Just then the doctor turns to us and says, “I can see you now, please.”

My aunt and I get up and head into the private room as the doctor walks in and my aunt takes a seat in the corner with a beautiful smile on her face.

“So what seems to be the problem?” Her voice almost sings out and suddenly I’m incredibly nervous about having to tell a female doctor about this.

“You look a bit shy, but don’t worry whatever the problem is I promise I’m a professional and I will deal with it in that manner.” She seems very reassuring and the smile on my aunt’s face even turns me on about telling her.

“Well doctor... it’s my... penis...” she seems a little shocked but she quickly hides it to keep her word.

My aunt then takes over and her words seem to make the doctor and myself begin to sweat a little.

“He can’t cum basically, he’s tired masturbation and sex but he just can’t make himself reach an orgasm.”

The doctor seems flustered but speaks up, “I’ve never heard of anything like this before... I suppose we need to do blood work to determine if something medically is wrong, however the problem may be psychological”

She then lifts my shirt and listens to my heart and evaluates my lung capacity, “Well you seem to be in great shape” She then turns to my aunt, “Are you his mother?”

To my amazement my aunt blurts out, “Yes.” and winks at me with a strange look in her eye.

“Well then has anyone in your family ever experienced anything like this before?”

“No I’m afraid not, doctor. I also forgot to mention that his penis is very big because of this problem and he feels pain if he keeps it erected for long periods of time.”

I thought the doctor would become completely disgusted by my supposed mother’s knowledge of this but she only takes off her glasses and begins to breath heavier as she glances at my crotch.

“Perhaps I should look at your penis fully erected.”

I felt so shocked but I wanted relief too much to ignore the help I might find here. I removed my pants and allowed my growing cock to spring to life. The doctor began to examine it and I saw a band of sweat forming on her forehead. She was professional as she grabbed it and looked at it from all sides, measuring the length and width. She could only gasp at her measurements and did it twice just to be sure.

“Did it hurt while you were having sex? Or does it only hurt when you masturbate?”

“Actually now that I think about it, it didn’t hurt at all when I was having sex”

“hmmm... well I have an unprofessional suggestion and that is to find someone to have sex with who can handle your size for a long time and just continue until you reach an orgasm.”

I could never have imagined a doctor telling me that I needed to find someone to have sex with! I looked at my aunt and it seemed like those were exactly the words she wanted to hear.

“Well being his mother, I had better be the one to try and help him”

I again thought the doctor would head for the nearest exit but instead she sat down and placed her chart on the table looking with lust at my erect cock.

“I suppose I better stay and make sure you can do this all by yourself...”

“O.k my son, just lay down and we’ll do everything we can to help you get through this.”

But I couldn’t just lay there, so I sat up and watched as my aunt moved towards me taking my shirt off and staring at my body. She started tickling my cock and my hands flew to her covered breasts. I rubbed and pulled until her nipples stuck out like rock hard pebbles. They were so big that I could almost use two hands to concentrate on a single tit! I pulled her t-shirt over her head and found she wasn’t wearing a bra as her breasts bounced free right in front of my face. I pushed the naked flesh into her chest and delighted as they bounced and giggled as she moaned in pleasure. She then took a step back and teased me by playing with her breasts, placing her hands on their undersides and pushing them up and down.

“I think mommy needs a milking”

Her lusty voice took me to another level and I quickly took her right nipple into my mouth and sucked for all I was worth. She ran her hands through my hair and pulled me closer into her tit. I then released her nipple and ran my tongue all over her right tit as I covered as much of it as I could. I then ran my lips through her cleavage as I moved to her other breast and used my free hand to pull on her erect nipple.

“Oh you bad boy, being so greedy like that! We do have a guest”

With that she moved towards the doctor who was rubbing her pussy through her clothes and offered her the wet tit. The doctor hesitated at first but then began gently sucking on her nipple which turned me on in a whole other kind of way.

“Mmmm, well that was nice but I think my son needs a little milking of his own”

My cock was at it’s greatest size and my aunt gasped as she knelt before me. She stuck out her tongue and teased the head of my cock, gently kissing it and beginning to get more and more aggressive.

“Oh mom” I said, “I always wanted you like this.... you’re so beautiful”