Tiny

Story Info
Stepmom helps out her stepson with his tiny problem.
9.5k words
4.28
182k
93
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jasliz
jasliz
3,523 Followers

***We posted this story previously and noted that it would have some typos and mistakes because we couldn't seem to find an editor. Well since then more than one person has contacted us with their willingness to help on this and other stories. We are re-posting the story with the edits and would like to thank Don for his exceptional help and time to find all the problems.***

The laughter echoed in my ears. It always ends this way. Every time I'm finally alone with a girl, thinking this will be the one, this is the moment I'll lose my virginity. As soon as they see my small penis they start laughing and it's over. They don't want anything to do with me.

Now I'm sure you're wondering. "How small could it possibly be?" Let's just say if six inches is supposed to be the average size of a male penis then I'm barely half of average. Barely and I can't even say it's at least a short fat cock. No, the girth matches the length in proportion. My fucking middle finger is bigger even when my cock is erect. When it's soft it is even more pathetic, most the time it's hiding among my normal sized testicles and all but invisible.

Now I don't know who to blame. They say the size of the penis is given to you from your father but I've seen my dad's dick and I didn't inherit mine from him. So that leaves my mother, and it's hard to blame something on a dead person. My mother died years ago when I was ten. Now ten years later and I'm still a virgin because of my tiny cock. I can't tell you how humiliating it is, how frustrated I am to be a twenty year old virgin. I guess it's better than being forty but twenty is ridiculous. Hell, I'm not even Mormon so I can't use that as an excuse.

Getting to know the women isn't an issue. I'm a decent looking guy. I work out, I'm over six feet tall and attracting women isn't the problem, it's the reaction I get when then see my tiny penis in comparison to my muscled tall body. They just can't handle it and laugh, sometimes hysterically.

This happened again just recently. I was dating a cute brunette named Jenny and we were hitting it off really well. After several dates she was beginning to wonder why I never invited her up to my place or went in to hers when she asked. I usually put off taking the relationship to the next level for a while, hoping the woman will be more attached to my personality and be able to see past the size of my dick. That hasn't happened yet.

Jenny was no exception. She finally dragged me up to her apartment and we started making out on the couch. My cock got instantly hard, it has no problem doing that since the blood fills up something so small very fast. Jenny pulled me over onto her and we continued kissing with my body between her legs, both of us fully dressed. She starts grinding on me as we kiss and moves my hands up her shirt to her firm breasts. I'm all sorts of turned on. My small cock was just throbbing in my pants and oozing all over my jockey shorts. After a while of this she stops kissing me and looks me in the eyes.

"Are you not turned on? Are you gay?" she asks.

"Gay? Hell no. Why would you think that?"

"We've been kissing and making out for an hour and I can't feel your penis at all between my legs. It's like you're not even into me?"

It was the moment of truth. I had no choice but to tell her or show her really. I pushed myself off of her and said, "I'm very into you. I'm as hard as I can get."

"What? Then why can't I..." she started to say as I was pulling my pants off.

The sight of my tiny cock arching upward made her stop midsentence.

"Oh," she said and started laughing. "I'm sorry," she said mid laughter. "I don't think this is going to work."

I pulled up my pants and left, like I normally do. She was still laughing when the door closed.

Depressed once again I got in my car and instead of going home to my apartment I drove to my dad's house. It was about ten at night when I pulled into his driveway. I got out and knocked, letting myself in. My stepmother, Julie came around the corner to the foyer as I closed the door.

"Oh, hi, Steven... what brings you by tonight?" she asked.

My father married Julie when I was fifteen, five years after my mother passed away. She basically became my mother but not really. At that age, I didn't really accept her as a stubborn, know-it-all teenager. She's seven years younger than my father, blonde and a yoga instructor so she's tall and skinny and, I'm sure, flexible. I never found her hot when I lived with them, I just considered her my stepmom but the older I got I could see what my father found attractive.

"Just driving by, nothing else to do," I said.

"Nothing else to do on a Friday night? I don't believe that. You seem upset," she said.

"Is my dad home?" I asked.

"No, he's playing cards with the guys at Dick's house."

"Oh, right... I forgot."

"Now tell me what's wrong... I know something's bugging you."

The frustrations had come to a head and I just finally let it out and spilled my guts to this poor woman.

"I'll tell you what's wrong, Julie. I'm twenty and still a virgin," I said, fighting back tears of all things.

"Oh... but... how can that be... you're a good looking young man. I've seen you with many beautiful girls."

"Exactly, many... haven't you wondered why they never stick around?" I asked.

"Not really... I just figured you moved on to another."

"Oh what, like after I did her? I'd go find another one to screw."

"Umm, well something like that. You seem very angry, Steven... what's happened."

"The same thing that always happens. They laugh at me!" I said, wiping tears out of my eyes.

"They laugh? Because of why? Your inexperience?"

"No... because of my tiny penis."

"What?"

"You heard me."

"But... how can that be... your father...," she trailed off.

"Yeah, well, I didn't inherit my dad's big cock," I blurted.

She hesitated and folded her arms under her enhanced breasts. She had the boob job before my father married her. As skinny as she was, her natural breasts were probably an A cup at best but she was sporting a healthy C with the bags of silicon.

"I don't know what to say, Steven... how small is it?" she asked.

"Small, like... well, you just have to see it," I said.

"Umm, alright..." she hesitated.

I undid my belt and pulled down my pants and jockeys at the same time. She gasped when she saw my shriveled up cock hiding in my ball sack.

"But doesn't it get larger when it's erect?" she asked.

"A little, but not much."

"Oh, I'm sorry, Steven. I'm afraid you have me at a loss."

"Yeah, that's how I feel too," I said pulling up my pants.

"I don't know what I can do to help," she said, wringing her hands together and shifting her weight to the other long leg.

"There is nothing you can do. I'm cursed forever. This was my last chance, tonight with Jenny. It's over. I'll die a virgin I know it."

"No you won't. Don't talk like that," she said, moving forward to embrace me.

I moved my hands around her body and she was able to get closer to me. I felt her breasts press against my chest and my stupid little cock started growing even hugging my stepmom. I broke the embrace, wiped my face again and left.

**

I felt terrible as I watched Steven leave. My poor stepson had just revealed two surprising things to me. He's a virgin for one and then the size of his manhood. I had to admit I was shocked, totally blown away when he actually showed me. I almost couldn't see it hidden among his scrotum. Even with his hair trimmed almost to nothing it was difficult to find. I'm sure he trims his hair to make it visible at all. I felt terrible for him. The strangest thing is his father is the exact opposite. Roger has a healthy above average penis almost nine inches long and wider than my largest finger and thumb when I hold it. Steven's was... well I have no idea because I saw it soft, but I doubt it grows to four inches or even three.

I couldn't imagine how he felt. He said they laugh at him. The girls actually have laughed at him when they see it. How horrifying for him. He's convinced he'll die a virgin and I had nothing to encourage him with. I felt like a horrible stepmother.

It weighed on me. I paced back and forth in the foyer after he left, thinking of what I could have said or what I could do now to help. I thought about paying for a prostitute. Maybe pay her to have sex with him but not reveal she's a paid whore. The problem was I didn't know how to make that happen. And if he found out, which was a good possibility, he would be very angry.

I felt worse and worse as the night progressed. Roger wasn't home, and probably wouldn't be until three in the morning. I usually just went to bed when he was out playing cards with his friends but that night I couldn't sleep. I kept racking my brain on how to help Steven. He wanted to not be a virgin; I think that was even more important than having a small penis. I'm sure he's come to accept that, and there really isn't much he could do about it. There is no miracle pill or exercises to increase penis size. Not really. So I focused on his virginity and what I could do to make sure he didn't 'die a virgin'.

It finally dawned on me what I could do. I was not his real mother. I could have sex with him. Maybe that would give him the confidence he needed to go on trying with other women until he found the one that would love him for who he was, not the size of his dick. It was a perfect plan to me. No one but Steven had to know. It would be a one-time thing, between he and I and I just knew it would help him.

I made my decision and when Roger came home I didn't mention anything to him. Not even that Steven had come over that night. Roger was surprised to find me up and the light on in our room. I watched him undress and he climbed into bed with me, turning the light out. When he snuggled up to my back I couldn't help but feel the large bulge hit my butt. I couldn't believe Steven was his son. The difference was staggering.

Curiosity got the better of me and I asked Roger a question I hadn't ever asked, "Was your first wife a virgin when you married her?"

I knew he had married her young, I think they were high school sweethearts.

"That's a random question," he said.

"I know, but humor me."

"Yes, she was, why?"

"Was she able to handle you the first time?" I asked.

"What's gotten into you," Roger asked.

"Just curious. You're so big and... well I was just wondering."

"Let's just say it didn't go very smoothly but after time she was okay."

"Steven's not adopted is he?" I asked.

"Wow, you're on a roll with random questions. No, he's not adopted. Why all the strange questions?"

"No reason. I've just been thinking," I said.

"What could you possibly be thinking to ask that set of questions?" he asked.

"Just about how much I love you and your big cock," I said.

"Oh, really? And how did Steven come up in that rational? You're not wondering if he's endowed like his father, are you?" Roger asked, rising to his elbow behind me.

"No, of course not," I said rolling over to face him.

"Is that why you were still up when I came home. Is someone horny?" he asked.

"Someone might be," I teased.

"Well, then maybe that someone should show someone else how much she loves someone's big cock," he said.

I started laughing, "Oh yeah, well someone might just do that," I said reaching down and grabbing his long semi hard shaft.

He flinched as I grabbed hard and then rolled over onto his back. Letting go, I helped him pull his shorts down and picked up his heavy shaft once again, stroking it to full height. In the dim light of the room I admired his long, thick cock, forcing it vertical to view the entirety as a silhouette. I couldn't believe the difference between it and what I saw between Steven's legs. Leaning over, I took Roger's head into my mouth and heard him moan with pleasure. He was wide, filling my mouth and stretching my lips wide. I could only take the first five inches in, because he was too wide for more, but he never complained since I usually stroked his other half while I sucked on his head.

It got me wet when I sucked him. Sucking something that large was a crazy turn on for me. I sucked until he was breathing heavily and I was very turned on. With one hand I wiggled out of my panties, leaving my nightshirt on and threw my leg over my husband. I gave him a few more good strokes before rising off of him and pulling his head back. With his shaft in my hand, I rubbed his head up and down my wet sex, opening myself and wetting my lips. Sometimes if I'm not fully ready for him, his width will snag and bind on my labia. Sitting down on him, I released his cock and eased down on all nine inches, no snags this time. It's amazing how full I feel when I take him into my body each time. I swear it takes my breath away without fail.

Suddenly his hands were on my breasts. He loves to play with my chest when I ride him. Over the shirt his hands felt good and they slid easily on the cotton shirt. My nipples hardened quickly in his palms and he was soon playing with them, pulling and pinching at his leisure. Using my legs, I rose and fell gently on his cock, probably only taking four to five inches out of my body before falling back down onto him. He was so wide I didn't have to move much to get the full effect of his penis. The depth was amazing and the girth stimulated my sensitive lips and walls perfectly.

I rode him for a few minutes, basking in the sensations rushing through my body with his hands on my breasts and the large cock in my body. Suddenly he rolled me over and took control. I lifted my legs and welcomed him between them. He already had begun thrusting and lifting my legs to let him in deeper until it felt like he was pushing into my abdomen with his length. I clawed his back and moaned as my climax burst over my body. I had almost achieved it riding him; he just finished me off with his hard, deep thrusts.

Sweet pleasure rushed through me as his cock continued to pound in and pull out. My sex tightened and released as my legs shook from the orgasm, he always seems to coax out of me. I loved his cock, loved everything about it and couldn't imagine anything else.

A few minutes later he collapsed onto me, his cock spewing his love deep inside my body as he moaned his climatic grunts. He held it deep until he finished and then rolled over, leaving me empty except for his plentiful seed. He was fast asleep within a minute.

**

I woke up the next morning with my cock hard like usual. Being a virgin has nothing to do with masturbation. I've jacked off for as long as I can remember, but have never had the privilege of putting my dick inside a woman. With as worked up as I got with Jenny last night, I needed a little release. As I started stroking my little cock with just my thumb and index finger, I found my mind was thinking about Julie hugging me and her round breasts smashing against my chest. I don't know why I remembered that more vividly than fondling Jenny's but I did. It didn't take long before I blew my wad onto my stomach, and some even shot up to my chest, which with my little cock is quite a distance. Just as I was cleaning up I got a text message. When I looked at my phone I was surprised to see it was Julie. I kind of felt strange and a little guilty for just masturbating thinking about her and then she texts me.

She was asking if I wanted to have lunch with her today. I was sure she was taking me to lunch to try and make me feel better after I unloaded my problems on her. I almost told her I was busy but another text message came through. She was going to take me to my favorite restaurant, her treat. I told her okay and that I would meet her. I couldn't pass up on my favorite ribs.

I showered, got dressed and since it was Saturday, I watched golf until lunch. I drove to the restaurant and went inside. I saw her sitting alone and smiled at the hot hostess and walked to Julie's table.

"No Roger?" I asked, sitting down.

"No, he had a client come in from out of town. It's just you and me."

"Okay, so I know what this is about," I said.

"You do?" she answered and she seemed genuinely surprised.

"Yeah, you feel sorry for me because of last night."

"Not sorry for you. I want to help, Steven."

"How can you help? Did you tell my dad what I told you, what I showed you?" he asked.

"No... I didn't even tell him you came over last night."

Just then our waitress came over. She was a tall brunette with big breasts that she liked to show off; probably to get better tips. I sure got an eye full as she leaned over and set my glass of water down. I wasn't complaining. She took our orders and touched me on the arm and giggled a little, flirting with me even with what I guess appeared to be my mother at the table.

"See that, Steven. She's totally into you. You shouldn't give up," Julie said.

"Yeah, they're all into me right up to the point where my dick has to take over. Then they laugh and are no longer into me."

"I can help," she said again.

"How? You know some way to make my co.... penis get bigger?" I asked, changing the word for her benefit.

"Not exactly, but I have something else in mind that I know will help."

"What? What could possible help?" I asked, taking a drink of the ice water.

"I will have sex with you," she said.

I choked on the water, actually spit it right out onto the table I was so shocked with what I heard."

People in the restaurant turned and looked and even our waitress came over asking if everything was okay. Luckily it wasn't as busy as dinner time. I explained that the water went down the wrong pipe and could we get some extra napkins to clean up. She smiled, touched my arm again and left to get the napkins.

"What they hell did you say?" I asked Julie as soon as the waitress was out of ear shot.

"You heard me. I want to help you not be a virgin. I think it will take a load off your mind. I'm not your real mother, Steven. We can keep it between you and I and it would only be a onetime thing."

"You're serious. You are actually serious!" I said, shocked.

"Yes I am. Are you totally against the idea? Am I not pretty enough or am I too old?" she asked.

I couldn't speak and thankfully the waitress returned with the napkins to give me time to wrap my mind around what my stepmother was saying. The hot brunette cleaned up the water and gave me another look down her shirt but I didn't even enjoy it since I was so taken aback by Julie, who was staring at me from across the table. The waitress filled up our glasses and told us our orders would be out soon.

"I don't know what to say," I said to Julie.

"Do you need time to think about it? Or am I way off base? Do you even find me attractive?" she asked.

"I find you very attractive. More and more the older I get," I said.

"So what's the problem?"

"The problem is I grew up from age fifteen to now with you as my mother! That's the problem."

"So, I've heard a lot of boys have crushes on their mothers. It's not like we are blood related. Just two consenting adults. I want to help and I think this is the way."

"So I don't die a virgin?" I asked.

"No, so you get some experience and have some self-confidence."

"What about dad?"

"What about him. He doesn't have to find out and besides I'm sure he wants the best for you like I do."

"Yeah, but I don't think that includes me screwing his wife."

"Okay, now that's enough. You wouldn't be screwing me. One time and one time only. Just think about it, Steven. You don't have to answer right now."

"I'll do it," I suddenly blurted.

I wasn't a fool. I knew this might be my only chance with a woman after all the rejection I've had in my life. She wasn't my mother. She was a hot older woman with tons of experience and a fucking Yoga instructor to boot. Who wouldn't take that offer?

jasliz
jasliz
3,523 Followers