Virginity Redux


She said, "Jack, I really like you, and I want to do this and more, but I'm nervous and a little scared because I've never done anything like this before. I mean, I let my two brothers see my breasts at the lake when I was 16, but there was no touching. They got naked too and showed me their hard dicks and I watched them masturbate. It was really exciting, but nothing else happened."

I told her I was nervous too, so maybe we could go slow, take off our clothes and just look at each other. She thought that was a great idea and together we stripped, making neat piles of clothing on a chair. I know I could hear our hearts pounding and our breaths quickening.

At first we just stood there staring, she was so white and soft with a sweet pot belly and chubby thighs that were firmly pressed together over nice small feet and red painted toenails. She looked like one of my sister's stuffed dolls except for those beautiful big tits and her very red hairy pussy.

Her breasts were very large, round and long, they sort of reminded me of two large, pointy, oblong bags covered with milky white skin and topped off with bright pink areolas that were at least 4 inches across, slightly puffy with small nubby nipples right in the center, and then there was her hairy pussy covered in bright red hair, just like the curly red hair on her head. I was so excited that pre-cum was dripping from my cock.

As I etched her image in my mind, she asked if she could touch me again, saying, "I've only seen my brothers' cocks that one time, but yours is so much bigger. How big is it?"

"Well" I said, "want to measure to be sure?" She nodded her head, never taking her eyes off my swollen cock. "Ok" I said, "do you have a ruler or something to measure with?" She nodded again and went to her dresser coming back with a soft measuring tape which she used for sewing. She placed the metal end against my pubis and unrolled it to the very tip, it measured just over 7 ¼" then I took it from her and wrapped it around the middle of the shaft where it measured almost 6" around and 2" across. She was fascinated.

She took the measure from me and wrapped it around her wrist and measured 6 ½" saying, "Look at that, you penis is almost bigger around than my wrist! Have you ever put that inside a girl?"

"Yes I have, and it fit just fine, but she was older, had a lot of experience and she was very, very wet at the time so I think that really helped," I said.

Her rapid breath revealed her excitement when she asked, "Is it alright if I play with it a while, you know, really check it out?"

"Sure, I said, that would be great, but I have an idea. What if we take our time and inspect and touch each other until we satisfy our curiosity, at least for now? You know, look at each an everything we want, no hold backs, what do you think?"

"That's a good idea, she gushed and laughed nervously, but I want to go first, is that Ok with you?"

"Absolutely, I said, what do you want me to do?"

She smiled a big, bright smile and exhaled a gush of air and said, "Well, just stand here by the bed for now and I'll just look and maybe touch now and then."

"Great, you go right ahead", I said.

And she did. I was scared that I'd cum as soon as she touched me, because this was almost the most exciting thing I'd ever done; but I somehow managed to hold on.

First she pulled me close and started by touching my cock all over, from top to bottom, carefully cupping my balls and softly rubbing the skin back and forth on the shaft. As I dripped pre-cum, she rubbed it on her fingers and over the head of my swollen cock and up and down the shaft.

"Wow, she said, your cock is so hard but so soft and your balls are nice and soft too. But, you're leaking, is that your cum I've been feeling?"

"No, I said, that's pre-cum, the lubricant that comes out to slick up your pussy to make sex easier, it comes out when I'm excited and stimulated like now."

She giggled and said, "It's nice to hear that I excite you, I know I'm not very pretty."

"Bullshit, I said, you are a very pretty girl, the prettiest girl I've ever been with and I am very happy that we are here together."

She blushed and turned away shyly and said, "Liar, but thank you anyway, I'm really happy to be here with you too. But, I'm not done looking you over Mister. Turn around please."

Around I went facing toward the open room away from the bed. She stepped up close and began to run her hands all over my body from the top of my head down to my feet, carefully exploring every part of me. She explored me more carefully that any doctor or anyone else I'd ever known.

Finally, she said, "Bend over please; I want to look at your bottom." Over I went, and then she spread my butt cheeks, tracing my crack from the bottom of my balls to the top of the crease. Then she knelt down and gently probed my butt hole, asking, "Is that Ok? You don't mind me doing this?"

What was I supposed to say? "No problem, feel free to do whatever you want", I said.

After a few minutes of touching, probing and sniffing, she asked me to turn around again. She stayed kneeling down on her knees. Once around, she took my cock in her hand, rubbing the pre-cum around and gently kissed and sucked the slit at the head of my cock, making little sucking and smacking sounds, it was very erotic and felt wonderful.

She did not suck the head into her mouth, rather kissing and licking my cock slit. After a moment or two, she stood up, pulled me down to her and kissed me full on the mouth, shoving her tongue into my mouth, frenching me deeply. I opened wide and let her explore the inside of my mouth and tongue, then pulled her close crushing her breasts against my chest and mashing my cock between us; I could feel her hairy bush against my balls, it was truly great. Her mouth and tongue were really wet and tasted sweet.

Then she stepped back and softly whispered to me, "Your turn!"

We were both breathing hard and her skin was flushed pink, clearly we were both really excited. I began by softly touching her face and neck; then I caressed her big breasts and began sucking on her pink nipples holding each of her breasts with both hands. As I suckled she began to breathe heavily, moan and sigh. I would lift up a breast so that I could suck on it and look at her face and I saw her eyes were closed and a small smile played on her mouth.

Then I grasped her nipples in between my thumbs and fingers and started to squeeze and roll them as I kissed my way down her little fat belly. Her skin was velvety soft and smelled of baby powder and sex. As I reached her bushy pussy, I slid my hands down and grasped her ass firmly and allowed myself to smell her bushy pussy and kissed it several times. Then I stopped.

I turned her around so that I could explore her backside as she had done to me. It was great; I'd never had this opportunity with a naked woman before. Every now and again I would reach down and stroke my cock for a bit, occasionally tasting my pre-cum, I've always like the taste.

After a few moments I asked her to bend over which she did quickly, then she reached back and grasped her bottom cheeks with both hands and spread them as wide as she could. Her fingers were white near the tips showing me how hard she was spreading her butt cheeks apart. Her little butt hole popped out under the stress and her pussy gaped open a just little showing me a bright pink tunnel in the midst of a fleshy depression.

"Does that help? She asked, and pulled a little harder."

"It's great, really great, thanks, I said."

I simply could not help myself, I eased my forefinger into her little pussy gap and gently rubbed it around, pushing it in and out slowly. "Oooooh, I really like that Jack, it feels so goooood!"

Then, I pulled out my forefinger and eased in both the fore and middle fingers, it was a really tight fit and I was going to pull them out when she shuddered and pushed back against my fingers, saying, "Oh damn, that feels so good, don't stop now."

So I kept up my slow finger fuck and began to probe her tight little brown butt hole with my other hand. She shuddered again and while breathing hard said, "Jack, I don't think I will be able to keep standing up if you keep doing that."

Realizing that her position was important to the success I was enjoying, I removed my pussy fingers and had her kneel down and bend over the bed with her upper torso on the bed and her bottom facing out toward me. It was a good plan.

Once she was in position, I knelt down and had her spread her cheeks again and reinserted my fingers in her pussy, slowly and gently finger fucking her as her breath quickened. As her bottom began to rhythmically move up and down and back toward my fucking fingers, I rubbed pre-cum on her asshole with my left hand, getting it nice and lubed and then began to slowly push the forefinger on my left hand into her ass.

It was a good idea, by the time I had my finger in her asshole up to the second knuckle, she began to ram herself backward onto my fucking fingers and make all sorts of huffing and grunting sounds. That alone nearly caused me to blow my cum load, but I managed to hold back.

Within seconds she let go of her ass cheeks and grabbed onto the bed sheets while burying her face in the bed, making "woo-woo, oh-oh-oh, Jesus, Jesus, Oh-Oh" sounds. Simultaneously, she sort of banged her pelvis into the edge of the bed as though fucking.

When she started that, I pushed my fingers as far as I could into her pussy and twisted them side to side and up and down until she became silent and still. Then I carefully removed my fingers from her pussy and ass. I gently rubbed the skin on her bottom and massaged her lower back with both hands until she rose up, turned around, knelt down and wrapped me up in her arms, mashing her mouth into mine. She held that position for what seemed like a very long time, then sort of sagged and slid down and leaned back against the side of the bed.

There were tears in her eyes making them all wet and sparkly and she smiled a big smile at me and said, "Jack Thompson, you are really something, where did you learn how to do that?"

"To tell the truth, I said, I have no experience at all, it just seemed like a good idea at the time, so you liked it? I said."

"I loved it; it was fantastic, like nothing I've ever experienced before. You sure you've never done this before? "

"Nope, said I, but I sure liked doing it and I sure like you liking it!"

She smiled her soft smile and looked down at my rock hard cock, seeping pre-cum and said, "Oh you poor man, I need to help you right now!"

"Pretty girl, it won't take much", I said.

"Jack, I was completely honest about my lack of experience, but I've watched porn on the internet so I think I could suck you off because all men love that, right?"

"I don't know about all men, but I'm pretty sure I would love it, I bet you would be a great sucker."

She told me to get on the bed and get comfortable, and then she sat down next to me and began rubbing my chest and legs, then my balls and cock. Finally, she leaned over and began to lick and suck the slit in my cockhead. It was incredible, after a moment or so she managed to get most of my cockhead into her mouth, running her tongue under the head teasing and softly licking the frenulum.

Her mouth was hot, it seemed scalding hot and she kept stroking my shaft so nicely that it was no more than seconds when my balls began to boil and I call out to her, "Sandy, I'm cuming, I'm cuming!"

She squeezed my cock shaft in a death grip and sucked the head of my dick like a vacuum cleaner; gulping and swallowing for all she was worth, but no more than a blast or two went down before she popped off with teary red eyes, coughing and choking on the cum in her mouth.

In the meantime, my cum blasts continued, two more big ropes of cum hit her in the face and on her beautiful big tits. Through it all, she kept stroking my cock, squeezing out even more cum that bubbled over my cock end, coating her hand and wrist, and dripping in a puddle onto the bed. My cock felt wonderful as it tingled and seemed to buzz and vibrate.

I lay on the bed panting and sweating, exhausted and more than a little scared that she would be mad about all the cum on her, in her and on the bed. But she smiled at me, a very sweet smile and said, "It looks like I did a good job, wouldn't you say?"

"No shit Sherlock, I said, I doubt anybody will ever do it better, not ever, you were absolutely great!"

"Could I get a hug? She asked."

"If you don't mind my cum, get up here and get your hug, I said."

And so it was that she eased on top of me and we hugged a great hug while wallowing in cum. After a few minutes we started to get cold and she said, "How about a shower and we change the sheets?"

"Done and done, I said."

When we stood up, all that cum was smeared over us so we went directly to her shower and turned it on. As the water warmed up we hugged and I sucked and nibbled on her nipples till they were nice and hard and she was all squirmy, breathing hard. Into the hot shower we went washing each other carefully and completely, not a hole, crease or crack was missed with tongues and hot soapy fingers. I really enjoyed washing her chubby bottom and her little fat pot belly, she liked it too!

Once we dried off, we pulled off the sheets, put a couple of nice fluffy towels down on the cummy wet spot and remade the bed. Sandy threw on a big comforter and we climbed into together and wrapped up, enjoying the intimacy and closeness of our naked bodies. Even though I had this nice big hard cock, all she did was spoon back against me, spreading her legs and tucking my cock between her thighs, firmly up against her pussy keeping it nice and warm. We went right to sleep, a very good sleep.

When I woke up the sun was high and bright, Sandy was kneeling on the bed with her ass next my face, gently sucking my cockhead, but I had to piss like a racehorse. "Sweet girl, I said, I must piss or die."

"Ok," she said as she lifted her mouth from my cock, "Go piss, in fact, let me go with you. I've never seen a guy piss, I've got a pretty good idea, but I want to see anyway."

Off we went, my cock bouncing like baseball bat in front of me with Sandy following me like a puppy. Once there, I could not piss, it hurt and I could not piss, my pisser just locked up. I explained the problem was probably bashful bladder and that she should leave.

"No, she said, let's run some water and see if that helps."

She turned on the shower and as it warmed up she pulled me into the water, asking if that would help. As she stood there in the shower with me I started to pee, not a little stream, but a full on piss blast just like a fire hose and it hit her right in her belly. She laughed and grabbed my cock and aimed it at her pussy, belly and tits and said, "Piss away big boy, piss away, this is fun!"

And I did, I pissed all over her, I even managed to hit her in the mouth. It was a first, but it happened many times over the next three years and we had lots of fun with it every time, who knew?

Once we dried off, with our teeth brushed we wandered back to the bed, I followed her closely watching her nice little fat ass jiggling all the way to the bed. I never thought I'd enjoy a chubby girl, but I was wrong. As she lay down on the bed she said, "I'm skipping school today, I think you should too?" I did. I lay down beside her and started sucking on those big soft tits, it was fun and she loved the way I sucked her nipples; rubbing her breasts while I sucked and she used her little foot to fondle my balls and cock until I was full on hard as a brick. She relocated to my cock, leaving her ass near my face.

I instantly decided that today would be a great day to eat my first pussy. I had her spread her legs, straddling my face while I pulled her ass up until I could easily start licking her pussy lips, she loved that, easing her mouth off my cockhead, sighing, "Yes, baby, yes, that's sooo good!"

With all the bushy hair it took me a while to get it spread out so that I could find her clit easily and then gently I began nibbling and sucking on that little devil. Sandy let me know she really liked it by pressing her pussy into my face so hard that I had to push her up so I could breathe. I told her if she killed me I could not eat her pussy anymore; she was more careful after that.

Before long I really, really wanted to fuck that pussy and I pulled my cockhead out of her mouth and got her turned around, saying, "Girl, I want to fuck your pussy, I want to fuck it so bad; will you let me?"

She looked at me very seriously and said, "To tell you the truth I'm just learning to get your cock in my mouth, I'm not sure that your cock will fit in my pussy, I'm a little scared."

"Ok," I said, "I promise that I will stop anytime you say stop and I will be very, very gentle, Ok?"

She nodded, spreading her legs as wide as she could, opening her pussy with her fingers, saying "Ok, but you be careful with me. Jack I trust you."

Because she'd been sucking on my cock she was very wet and I was dripping pre-cum; so I placed my cockhead on her open pussy and let it get really lubed up, rubbing my cockhead up and down on her open pussy and hard clit getting a nice little gasp each time. After several minutes I began to push my cock into her pussy, very slowly, until the head was almost fully in when I saw how big her eyes were.

I asked, "Am I hurting you?"

She took a deep breath and said, "Just be slow, it hurts but not too bad."

I continued pushing gently until I was in a couple of inches then I hit some resistance, I knew she was good and wet, so I looked questioningly at her. She said, "It must be my hymen, I thought you would have broken it last night, but I guess not."

"Can you leave your cock where it is and lean down here and kiss me?"

"Absolutely," I said, "kisses would be very nice."

So I leaned down and started kissing her, the girl loved to suck my tongue and be tongued. We kissed for a while and she whispered to me, "I know it will hurt; but, can you just push that big cock of yours into me and break through my hymen. I'll just grit my teeth and take it, Ok?"

I smiled at her, took a deep breath, eased my cock back and forth a few times and then jammed it in as hard as I could, a real ass driven cock driver. Suddenly things gave way and my cock went in a good 5 inches, there were still a couple of inches in the open, but I was way, way into her pussy. She had big tears in her eyes and flushed a bright pink, but she took a deep breath and squeezed me really hard, putting her chubby legs as far around my waist as she could, saying to me in a loud insistent voice, "Jam it in, all the way in, pound it in, jam it in, damn you big bastard, jam it, come on!!!"

I had pulled my cock back 3 or 4 inches and when I saw and smelled her bright blood on my shaft; something hit me like a bolt of lightning, there was a loud roaring in my ears like a train, I felt my nostrils flare, I began to take deep breaths, I felt like a great bull in heat ... brother this heifer was going to get a serious fucking.

I remember hammering my cock balls deep into her pussy, once, twice, again, again and again. I felt like a man possessed, I was a cock driving machine; I pounded her pussy violently shaking her whole body. I heard her breath whoosh out and her groans filled my ears, but nothing would stop me I was a fucking machine, fuck -- fuck -- fuck, I'm not even sure I could see, fuck -- fuck -- fuck until my balls boiled and blast after blast of cum jetted out of me deep into her pussy.

Later we decided that I pounded her pussy for 20 or 25 minutes, relentlessly, without mercy, until I blasted her with cum and then slowly collapsed onto her belly and those lovely, bit soft tits. I lay there for several minutes until my pounding heart slowed and my mind returned to near normal.

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bydragonwriter© 5 comments/ 65656 views/ 12 favorites

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