The Scared Virgin
This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE
These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Tiny By jasliz (edited version)
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 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 frustrating it is to be a twenty year old virgin. I guess it’s better than being forty, but twenty is still ridiculous in this day and age. Hell, I’m not even Mormon, so I can’t use that as a reason.
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 into 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. This 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 mid-sentence.
“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 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?”
“Um, well, something like that. You seem very angry, Steven… What 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.”
“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.
“Um, alright…” She hesitated.
I undid my belt and pulled down my pants and jockeys at the same time. She gasped when she saw my shrivelled 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 laughed 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 wracking 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 humour 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 a 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 sleeping 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 then 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 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 to 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 favourite restaurant, her treat. I told her okay and that I would meet her. I couldn’t pass up on my favourite 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 felt 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 possibly 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 earshot.
“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 me 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 water 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 rejections I’ve had in my life. She wasn’t my mother. She was a hot holder woman with tons of experience and a fucking Yoga instructor to boot. Who wouldn’t take that offer?
“Oh, well good then,” she said, a bit surprised.
“When,” I asked.
“Well… I haven’t thought that far ahead.”
“How about now?” I said.
“Now?” She asked, stunned.
“After lunch. Dad’s busy. We could go to my place. It’s only five minutes away.”
“Umm… Well… Okay,” she said hesitantly.
“Hey, this was your idea, not mine,” I said.
“No, you’re right… Okay… After lunch,” she said confidently.
I wasn’t expecting Steven to accept so quickly or at all, really. I was a little panicked and it was difficult to concentrate on my food when the nice waitress brought it out to us. Steven, on the other hand, ate all his ribs and ate them fast. My proposal was already making a difference in his mood and outlook. I knew it would but now I had to go through with it.
After he scarfed his food he sat there like a little boy waiting for his presents. I ended up eating half my meal and the pretty waitress returned to see if we needed anything like desert or boxes.
“No, just the check please,” Steven blurted, anxious to leave.
“I need a box and the check would be fine now,” I said calmly.
I looked at Steven after she left and I swear he was vibrating. “Calm down, son… I’m not going anywhere. You’re going to work yourself up before we even get to your apartment.”
“I’m sorry, and could you not call me son… At least not for the rest of the day?” He asked.
“Sorry, Steven, I’ll act more the part from now on. Do you want to hold my hand on the way out?” I asked.
“Umm… No… I mean… I guess… If you want to.”
I smiled. He hadn’t realized I was teasing him. He was too focused on what was about to happen. I guess I couldn’t blame him. I decided to be serious and treat this as important as he did. The waitress brought the box and check. I paid and Steven and I walked out of the restaurant together, but we didn’t hold hands. He got in his car and I got into mine. He was out of the parking lot and heading to his apartment before I had my car started.
I pulled up to his apartment building, parking in a visitor slot and walked up the stairs to the second floor. His door was open and I walked it to his place. I had been there before, but never without Roger. It was a typical twenty year old bachelor pad, messy with a lack of furniture. The only thing worth much was the entertainment system. He had a big screen TV, gaming systems and a sound system to make it all really loud if he wanted.
I shut the door and locked it, placing my keys on the old coffee table Roger had given him when we bought new stuff. So far I hadn’t seen Steven and I figured he was in his room cleaning up as fast as he could. He suddenly appeared, out of breath and his face was red, from his bedroom.
“You don’t need to impress me, Steven. I’m a sure thing,” I said, smiling.
“I know… It’s just… It was a mess in there since Jenny was here last.”
“I appreciate the effort.”
He kind of didn’t know what to do, just standing in the small hall that led to his bedroom. I had to admit, this was new to me. I haven’t had sex with anyone other than Roger since I married him.
“So… What do we do next,” he asked, clapping his hands together.
“Well, you can invite me into your room and we can try to act natural and see how things progress.”
He did and I followed him into his room. The bed had been hastily made and there was a pile of clothes in one corner, he had hurried and thrown there. The blinds were closed and he had a ceiling fan going with the light on. It wasn’t very big nor was it a totally fabulous place to lose your virginity but it would work. I walked in and sat down on his bed. He fidgeted and moved a few more things around until I called his name and patted the bed next to me. He finally came over and sat down next to me. I could tell he was nervous… I mean really nervous.
“Just relax. This is supposed to be fun,” I said, taking his hand.
He was shaking. I lifted his hand and placed it on my left breast, hoping this was calm his nerves. His hand was warm, I could feel the heat through my shirt and bra. He finally moved it, squeezing gently and I could tell he had experience in fondling a woman’s chest. The experience was not lost on me. I admit my heart was beating fast and the idea of my stepson touching me this was giving me quite a thrill.
His other hand found my right breast and I felt my nipples begin to rise as he gently squeezed and rubbed them. I didn’t know if kissing him would be too weird so I didn’t try. I’d let him decide if he wanted to.
“You’re good at this,” I said encouraging him.
“Thanks, this is usually as far as I get,” he said finding my nipples with his thumb and finger.
I cooed at his touch and reached for his chest as well. He was well muscled, with a strong young body and it spurred my arousal to touch him. He, after all, was a very attractive young man. I could tell he was used to just fondling and touching and it was almost like he was afraid to go further because I’m sure that was when the rejection happened. So I pushed the issue.
I stopped playing with his chest and arms, grabbing my shirt and pulling it over my head. I unclasped my bra and enjoyed the reaction on his young face. He liked my enhanced breasts, just like his father. I lay down on his bed and he began touching me again. It was much more simulating flesh to flesh and I felt myself getting wet as he brushed my hard nipples and teased them with his fingers. I let him play for a few minutes before, lifting my arms and pulling his head to my chest. He was a little less experienced with his mouth. I could tell he hadn’t had much opportunity to lick and nibble on a woman’s breast. He learned quickly and took to sucking and nibbling them after a few minutes with my encouragement.
While he sucked and played, I shimmied out of my shorts and panties, kicking them to the floor. I lay there completely naked with my stepson enjoying my breasts. It was quite a thrill. His big hands betrayed what was really between his legs, but felt wonderful on my upper chest, stomach and legs. He was still fully dressed, another sign he was afraid to undress because of his fear of rejection. I let him continue. It was nice to be pampered and I took full advantage of his eagerness and presence in the moment.
His large hands finally moved up my inner thigh to my waxed sex. I was very sensitive from the pampering and the pleasure electrified my body when he grazed my lips with his hand.
“Have you ever pleased a woman with your mouth, Steven?” I asked.
“Yes, a few times before they tried returning the favour.”
“By all means, show me,” I said.
I spread my legs and he went down on me with his mouth. He knew where my clitoris was right off the bat so I didn’t have to teach him that. He also worked his hands well, spreading me with his fingers while sucking on my clit and using his tongue lower, just above my vagina. Two of his fingers entered me and curled upward as he flicked my clit with his tongue. He had done this more than a few times, the liar. I didn’t say anything; instead I grabbed the sheets on his bed and arched into his face. He feasted and fingered me until I came.
It was surprisingly good. The excitement of the moment and the thrill of who was eating me, made me climax long and satisfying. I was impressed by his talent, but his oral sex and fingers only made me hunger for something I was afraid he couldn’t give me.
Damn, my stepmother was hot! She was sexier with her clothes off, than on. I couldn’t believe how toned and fabulous her body was for a woman her age. That Yoga was amazing. Her breasts were stunning. The doctor did an excellent job; I couldn’t even see a scar on either of her round, firm breasts. She had no tan lines either, but was a nice even colour, not too dark and not stark white. Her stomach was mesmerizing, extremely defined, but not overly muscular. Her core strength must have been insane. Her legs seemed to go on forever with toned perfection and she had waxed her person hair completely away, leaving her sex smooth and gorgeous. My cock was rock hard before I had even touched her and now, as I sucked her nipples, I thought it might start cumming on its own.
Talk about a thrill. I hadn’t had a girl naked in my bed and gone this far with her for a long time. My heart beat rapidly in my chest and the sensations in my hands and mouth along with the visual perfection before me, just fed my arousal. The tactile pleasure was off the charts. When she asked me if I’d done oral sex before, I was thrilled to get another chance. That has been a while too. She tasted tangy, but smelled like body wash and I dug right in, sucking her clit as soon as my mouth covered her sex. With two fingers I spread her open and slid them into her. She was hot and wet and thanks to my dad, loose.
I curled them toward me and sucked her clit and flicked it with my tongue. She seemed to like what I was doing. I felt her legs tighten and her hands and dug into my bed. She never told me to do anything different so I continued to root around inside of her with my fingers and flick and suck her engorged clit. It got really hard and firm the more I teased it.
I’m pretty sure I made her cum. She started to shake and gasp for air, clawing at the sheets and began squirming so much; I had to keep finding her clitoris among her movements. She finally grabbed my head and lifted me off of her. I stopped munching and watched her quiver for a few more seconds before she opened her eyes.
“Very nice, Steven. Any woman would be lucky to have you do that to her anytime.”
She sat up and motioned for me to sit back on the bed. She helped me out of my shirt and reached for my pants. I grabbed her hand out of habit, afraid to show her my tiny cock.
“It’s okay, Steven. I’m not going to laugh or leave. Trust me.”
I let go of her hands and she undid my pants and helped me out of them. My little cock was fully hard, extending just three inches off of my body but oozing profusely. She looked at it and smiled. But it was a nice smile with no laughter and I loved her for it.
She reached forward and took it in her hand, covering the whole of it easily. Her palm caressed the head and the sensation curled my toes. She used my pre-cum for lube, pressing down with her palm and circling my sensitive head. I jerked and tried to pull away from her. This got a giggled out of her.
“Sensitive, aren’t’ you? Have you ever had a blow job?” She asked.
“No… Once they see it they laugh and leave, telling me that this isn’t going to work.”
“Well, I think it’s time you experienced what a woman’s mouth feels like.”
She quickly leaned over and my mouth dropped open in amazement. To say I had never felt anything like it would be obvious since this was my first time. To say the sensation was mind-blowing would lessen the actual sensation. It was beyond words. The heat, the wetness, the first time she sucked, rocked my world. She of course was able to take all of my small cock into her mouth and wrap her mouth around the base. I felt her tongue work my head, shaft and she even licked my balls with my cock in her mouth. But when she started sliding up and down it with her mouth tight around my narrow shaft I was gone. This sensation was heavenly and brought me to the verge of climax so suddenly I almost forgot to say anything.
“Mom… Julie, I’m going to cum!” I said.
She suddenly removed her mouth and pinched the head of my cock with her thumb and index finger. It stopped my orgasm and she raised her head, but still kept her hand on my head.
“You’re too excited. I don’t blame you for your first time. I tell you what. I know I said only one time, but I didn’t mean orgasms. I’ll let you cum in my mouth, because you haven’t ever done that either. Then, at your age, I’m sure you’ll be able to get erect again soon, to lose your virginity. How does that sound?” She asked.
I could only nod. What she had said took a moment to process. I couldn’t believe she was doing this for me. She smiled and again her head fell into my lap, her hand was replaced by her warm, wet, velvety mouth. Holy fucking shit! My arousal spiked the moment she descended down my shaft. I was right back on the verge again, but wanting it to last. I had to concentrate and delay my orgasm because I didn’t know if this was ever going to happen to me again. I tried to think of something else. I actually closed my eyes so I wouldn’t watch her head bobbing up and down or see her breasts or tan sexy back. I ended up lying down on my bed as she slowly sucked my cock and caressed my tight balls with her fingers.
I felt like I was floating and the room was spinning. The euphoric bliss, I’ll never forget. She was soft and gentle, I knew she was trying to make it last as well, giving me the blowjob to remember. She would take me out of her mouth and just lick my head and shaft with her tongue, up and down it and over the straining head. She found a spot just between the V shape on my head that was super sensitive and she must have known it was because she licked it a lot and curled my toes.
I never wanted this pleasure to end. She was keeping me just on the verge of ejaculation and it was the most phenomenal experience of my entire life up to that point.
“You’re doing great, Steven,” she said, pausing her sucking for a few seconds.
I couldn’t respond. My body was vibrating and totally rigid from the head down to my straining toes. My balls were tight, my butt clenched, just waiting for her to take me past the point of no return.
“I think it’s time. Don’t worry about telling me, just cum when you want to,” she said.
Her mouth took me inside again. Her lips gripped me tight and down she went those quick three inches to my body and back up. She sucked the head and descended again. Her grip increased, the pleasure mounted and I passed the point, tightening my muscles to hold my load in for those few blissful seconds before they gave in and the semen was unleashed. I had trained my body to do this when I masturbated and the training had paid off. I held it and held it until the surge was impossible to stop. My body jerked and the contractions took over everything else. My cock exploded inside my stepmother’s mouth. It was like no other orgasm I’d ever had. My hand could never simulate a woman’s hot, wet mouth during ejaculation. Hands down, this was the height of my sexual climaxes. I felt the semen surge forth in rapid succession. She kept her mouth around my cock for a few seconds, but finally she released me and my cum sprayed up onto my chest more than I’d ever seen it before.
It was worse than I thought. I forced a small smile when I saw his tiny penis. He barely extended the length of my index finger and was about as thin. To cover my shock, I quickly grabbed it and tried to focus on making him feel good. It felt like a cock, but it didn’t. It was almost like a play toy or a gag gift cock it was so small. He reacted like a normal man when I spun my palm on his slippery precum but it just felt so weird to me. I had to distract myself from how small it was by asking him questions and then finally I just put my head into his lap and started sucking it. I had the distinct thought I was sucking a little kid. I thrust that out of my head and got too aggressive to keep my mind off of how small he was. He suddenly called me Mom and then Julie, telling me he was going to cum.
He was so excited and I was unfortunately not. I pinched his tiny head and stopped him from cumming so soon. I felt selfish and disgusted with myself and decided to let him cum in my mouth and still have sex with me. I was trying to help him and needed to suck it up and focus on his pleasure and forget myself. I couldn’t compare him to his father or anyone. This was Steven, the boy I loved and who I’d been a mother since I married his father. I could focus on him and make him feel good, give him experience and confidence.
He laid down after I started sucking again and I changed what I was doing. I knew what would make him ejaculate and instead, I used my tongue and licked him more than sucked him. His little cock was straining the entire time. I kept him very close and licked and pampered his tiny cock for several minutes, telling him he was doing great. His normal sized testicles were tight and had formed a single taut lump under his little shaft. I caressed the wrinkled flesh as I licked and treated him to the best blow job I knew how to give. Especially on such a small penis. It was challenging just to do the things I knew how to do on a normal sized cock. Where I could use my whole hand ended up being just my finger and thumb. Where I could stimulate the head of a cock on the roof of my mouth, I was forced to use my tongue because he didn’t go deep enough. It was the strangest blow job I’ve ever given.
The big surprise was when I finally brought him to orgasm. For some reason, I guess because of his small cock, I expected a small load. Boy was I off. This kid ejaculated more semen then I’d ever felt and seen in my entire life. At first I tried to keep my mouth around his shaft as his cock began to explode, but then more and more continued to spray out with incredible velocity and volume. I was forced to remove my full mouth just to breath and his little cock continued to spray an amazing amount onto his quivering body.
By the time he finished, he was covered from neck to balls in lines of white, not to mention the mouth full I let out of my mouth on his stomach. It was staggering to say the least.
“Good heaven, Steven! Do you not masturbate either?” I asked, shocked.
“No, I do… I just was excited.”
“Is this normal?” I asked.
“No, not really. I usually have a lot, but not like this.”
“Oh my… I’ve never… We need something to clean this up,” I said, leaving his room to gather my thoughts.
I went into his bathroom and looked myself in the mirror. “Could I do this?” I asked myself. Could I go through with this and have sex with him. How was I going to make it through? I knew I was going to have to fake enjoyment. After his father, I doubted I’d even feel him inside me. His fingers were much bigger than his little penis. This was going to be really hard. I gathered myself, found a towel and returned to his room.
He hadn’t moved and his little cock had shrunk to what looked like a small lump of skin. I force my eyes away from it and helped clean him off. He sat up once we had wiped him clean. He was smiling.
“Julie, that was amazing! So good I can’t tell you,” he said, animated.
I knew I had pleased him beyond his ability to describe and this made me happy. I just had to focus on that. ‘Make Steven happy and not worry about me’ was my goal. I sat down next to him and he immediately grabbed my breasts again.
“I can play with you again until I’m hard,” he said, like a little boy eager to go again.
“Okay,” I said and laid down for him to explore my body. He did have great hands and I took comfort in that.
I was having the best day of my life. I had just cum more jizz than I’ve ever seen in my life. I had been so excited and boiling over that when I finally let go it was unreal. I shocked Julie; she hadn’t seen anything like it before either. That made me feel really good. After she got me a towel I had gone soft but I knew that wouldn’t last very long, especially when I started playing with her fabulous tits again. She laid down again and I had both my hands busy caressing, palming, pinching and tweaking her nipples. Not hard, but enough to make her nipples erect and fun to start sucking on, which I did.
Five minutes hadn’t gone by and I felt my cock start to grow as I licked and nibbled on her nipples, back and forth, giving both equal time and I caressed her incredible stomach and long legs. Once I knew I was hard, I began fondling her sex and playing with her engorged clitoris before fingering her again. She moaned and cooed from my mouth and hands. It was fun and enjoyable, so I just kept going, not caring about having sex for the first time, since I was sure I was going to now.
Several minutes passed by before I finally moved over between her legs. She opened her eyes and looked up at me.
“Are you hard already?” She asked.
I smile, “Have been for a while now.”
“Oh… And you just kept playing?” She asked.
“Yeah, I was enjoying myself.”
She grinned, “It was nice. You’re really good with your hands and mouth.”
She looked down and saw my little cock pointing right at her. I placed my arms to her sides, holding myself up. My heart had increased significantly now that I was lying between her legs. I was excited. I could hardly wait to see what felt like the slide inside her. She put her hands up on my chest and traced her fingers around my muscles and ABS.
“You’re shaking?” She said.
“I’m just excited.”
“I understand, Steven. Well… Go ahead… I’m ready for you,” she said, smiling.
It was the moment I’d been waiting for, for a long time. I looked down at her body and down at my throbbing cock. It was only a few inches from her sex. All I had to do is move forward and I would enter her and my virginity would be gone. I couldn’t believe how fast my heart was racing and I hadn’t even entered yet. I looked up at my stepmother’s face and she encouraged me with her eyes.
I eased forward and the tip of my cock made contact with her sex. It was hot and my breath caught in my throat as the head passed into her wet tunnel. The next three inches eased into her and our bodies came together. I didn’t move, basking in the experience and the heat and sensation on my little cock. I was no longer a virgin.
She put her arms around me and pulled me down onto her chest and together we lay like that for several seconds as my heart pounded and my breathing was quickened.
“There you go, it’s okay, just breath,” she said in my ear, caressing my back.
“It feels… Amazing,” I said between pants.
“Good, it’s supposed to.”
I knew I was supposed to be moving, thrusting in and pulling out but I was just caught in the moment and hadn’t moved since I fell onto her body. She was so patient and understanding I was amazed how empathetic she was. The sensations going through me were surreal. Not only was my cock in heaven, feeling her breasts and naked body beneath me was a total body experience. I felt hot all over and tingly.
She encouraged me again with her hands, rubbing my back and down to my ass, squeezing my cheeks and putting her long legs around me. I got the hint and pulled my cock out until I could only feel my head inside her wet sex. I thrust back in and my vision went blurry. It was everything I thought I would be. It felt unreal. She cooed as my body hit her again and I pulled back out. My breathing and heart rate never calmed down. I was just too excited.
Even after the blowjob and the massive climax, I could feel my body approaching climax. I never have had an issue with pre-mature ejaculation when I masturbate, but having sex for the first time made me feel as if I did. My balls snuggled right up to my body and it was just so stimulating I was going to lose it soon.
“That’s it, Steven, keep going… That’s perfect,” Julie was saying as she held me.
“I’m… Going… To… Cum… Soon,” I breathed.
“Good, cum inside of me, don’t stop,” she encouraged.
It hadn’t been very long since I first entered her, but I couldn’t stop it from coming. She didn’t want me to stop apparently or slow down so I kept thrusting in until I couldn’t hold it. My cock began to ejaculate and that was when I felt the most incredible sensation. It was totally different then my hand or her mouth. My ejaculation cock was encapsulated in her warm, wet insides as it came and the added stimulation on my head and shaft was phenomenal. I groaned and shook as my cock sprayed forth and kept contracting over and over. My hearing faded out and my vision blurred as the pleasure was off the charts. I finally collapsed onto Julie, panting and overcome with pleasure. She held me, rubbed my back as my body continued to flinch and contract from the aftereffects of my first time.
I got very wet and turned on again as Steven sucked and nibbled on my breasts and fingered my sex. His hands were very gifted and I lost track of time, just enjoying the pampering. It was nice to feel worshipped and to have a man so present to my needs again. Suddenly, I felt him slide over my leg and his body was in-between my legs as he held himself over me. I opened my eyes and looked up at him. I shouldn’t have been surprised to learn he was already hard. He was, after all, only twenty. He looked so excited so eager to finally lose his virginity, he had apparently been hard for some time but continued to play, which I found endearing.
I put my hands up on his chest and the poor boy was shaking he was so excited. I could feel his heart beating so fast in his chest I thought it might come through. I smiled at him, and told him to go ahead and I was ready. In reality, after his hands and mouth, I was probably ready for a baseball bat. He hesitated as if he was thinking about something or just stuck in the moment. Finally, he moved forward and I felt a little tickle on my lips and our bodies came together. His face showed extreme pleasure and I figured he had entered me, but wasn’t totally sure. He froze and I could feel his body shaking and his heart hadn’t settled down. I could feel it pounding on my chest.
I caressed his back and told him to breathe. I wished I could have shared in his experience a little better. He seemed so excited and in the grips of ecstasy he’d never felt. For me it was unfortunately different. It just felt like he was lying on top of me naked. I felt something between my legs, but nothing significant enough to categorize as good.
I finally had to encourage him to move, or he might have laid there indefinitely. Using my hands, I rubbed his back and finally grabbed his ass and moved my legs around him. He finally started moving, rising up so he was barely off of me and then back down. I felt a little brush of something on my labia, one side then the other, but I was horrified for him because he was doing nothing for me. I couldn’t help but think of other women and what it would take for them to do this in a long-term relationship.
Somehow he was stimulated though, I couldn’t quite explain that. He started moaning and breathing heavier, as if he was already nearing his climax. To urge him on, I told him he to keep going and that it was perfect. It was an innocent lie, to make him feel good. He said he was going to cum and I was grateful, telling him to continue and not stop. A few seconds later he began to climax and that was when I started feeling more pleasure. His amazing load from before was duplicated inside my vagina, filling me up where his cock had not. It kept spraying inside of me until I was full and then began to ooze out around his shaft and down to my butt. The warm, thick semen felt good and I felt full for a short time at least.
He quivered and shook, groaning as he came and I held him tight, giving him his first experience he so desperately wanted.
I had gone through with it and I think pulled it off without him suspecting that I didn’t enjoy it as well. He finally rolled off of me and lay there staring up at the ceiling in a sort of daze. His semen was running out of me and it was a lot. There was nothing I could do to stop it.
“Julie, that was, that was awesome!” He blurted.
“It sure was. So how’s if feel to not be a virgin?” I asked him.
“Again, so awesome!”
I giggled and smiled at him, but didn’t move.
“Umm… Can you find that towel again?” I asked, looking at him and then down my body.
“Oh… Yeah, sorry.”
I put it under me and excused myself to the bathroom. It took a few minutes before I felt empty enough to go back and get dressed. I felt good about what I had done. I had no guilt and didn’t even consider it cheating on Roger. I was more concerned about helping Steven. I hoped the experience would give him the confidence he needed.
I got dressed and he thanked me, giving me a big hug and saying how much he appreciated what we did.
“I’m glad, Steven, but that was it… I want you to find a girl. This can’t happen again. Is that clear?”
“Oh, I totally get it. I’m not going to give up… I promise.”
I turned to leave and he walked me to the door. Just as I was about to open it a knock sounded on the other side.
I opened it to find a petite, beautiful brunette standing there, looking anxious.
“Jenny?” Steven said from behind me.
“Oh, you have company,” Jenny said.
“I was just leaving… I’m his stepmom, just came to visit,” I said, trading places with the nice looking girl.
This puts Jenny right in front of Steven. She looked nervous and so did he. I remembered what he had told me had happened the last time they saw each other. I stayed for a little longer outside his door, waiting for one of them to speak. She finally did.
“Steven, I owe you an apology… I was… I was way out of line,” she began and I closed the door after smiling at my stepson.
I had high hopes for him and Jenny. Especially if she came back to apologize. With a grin on my face and quickness in my step, I hurried to my car. I was hoping Roger was home when I got back because I needed a real cock and I needed it badly.