Go Ahead Ch. 02

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Continuation of a young man's exploration with a woman.
3.4k words
4.46
31.6k
12

Part 2 of the 3 part series

Updated 11/01/2022
Created 02/07/2014
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First of all, I want to thank you those of you who took time to read my last story and I really do appreciate the positive comments and votes for my submission. For those of you who are just opening this as a random story, you might want to read "Go Ahead" as this is a (hopefully decent) continuation of that story.

As I told you in part 1, Charles and Margie were my neighbors who were about 10 years older and had watched me grow up through my teen years. We had become friends and she was, on more than one occasion, the center of my imagination as I "pleasured myself". At the ripe old age of 18, things took a turn that I never saw coming...

I can still remember everything seeming to be in slow motion as she seated herself on the cushion near the center of the couch while pulling my hand in her direction. I watched carefully as she started to unbutton her blouse the rest of the way. I was mesmerized as her bra came into view. I started to sit beside her, but she started reclining lengthways on the couch taking my hand and pulling me on top of her.

Just for the record, I will once again have to admit, I had been in the arms of a female before this, either in a car or on a couch in the living room while her parents were in the den watching TV or something. But honestly, I never tried to do anything more than "cop a feel" (if I was lucky) while steaming up the windshield. We were mostly into kissing, hugging and groping around. I actually was a pretty decent kid and I only dated decent girls growing up. I might have gotten away with more, but back then I was happy with what I got and didn't want to screw it up. A girlfriend was a valuable thing at that age, but this was not a girlfriend, this was a woman... This was Margie.

I had read enough of the magazines to know the fundamentals, but I was scared, nervous, and excited, as I came to rest above her on my hands and knees. She once again, threw her arms around my neck and pulled my face down to her lips for another kiss. My inexperience had me hovering above her and as she broke the kiss, Margie told me to relax and lay down on her. I explained my concerns for her safety and comfort since I was so much heavier when she spread her legs and hooked them around my thighs guiding me down on top of her. "Now, isn't this better?" What could I say? I was in heaven.

Lying in the arms of a woman for the first time is one thing, but lying in the arms of Margie, the woman that I had fantasized about for years, was a dream come true. We made out for several minutes when I realize that she had maneuvered us somewhat into a side-by-side position with me on the edge of the couch on my left side.

It was during a brief pause in our kissing that I looked down to see her shirt had pulled to one side and her bra was on full display to my eyes. She touched my chin and lifted my face to look into her eyes and said "I remember you trying to sneak peeks at me that first day we met years ago. You were so cute. Now it's time for a real look" and with that she reached down and snapped the clasp between the cups of her bra.

I remember my first thought being, 'What the heck? I thought all bras opened from the back!' Her bra seemed to spring open and once again she proceeded to overwhelm me with the sight. I cannot describe the feeling at that moment. As with most young men, I had (and still have) a fascination with breasts and now Margie's were on display before me in all their glory.

As I described Margie before, she was a petite woman so she was not huge by any means, probably a 32B cup but right then she might as well been 40DD. They stood up off her chest firm yet were large enough that they had a slight jiggle whenever she moved. They were so soft, capped with nice half dollar size areolas and big hard nipples that were almost the size of a 1st grade pencil eraser. To this day, one of the things that really turn me on is a pair of nice size nipples. I think she set the standard for the rest of my life.

I am sure I was staring with my tongue hanging out when Margie giggled and said, "Go ahead baby, they won't bite". I was like a kid in a candy store. I have no idea how long I looked, touched, explored, and caressed her breast watching her nipple grow before my eyes, until she pulled my face to hers and we kissed again. Once again, her tongue touched my lips and she was moaning in my mouth as I squeezed her tit. She broke the kiss and shifted a little saying, "Don't forget the other one". She smiled again and with that, threw her leg over my hip and attacked my mouth.

It could have been a minute or 15 minutes. Time seemed to stand still and I do not have a clue as to how long we stayed that way. We were kissing and she was encouraging me to get familiar with her breasts. I did not care. It was truly the best day of my life.

Finally, we came up for air and stared at each other, her eyes searching for something. Her blue eyes seemed to sparkle when she smiled at me and asked if I was okay. I am not sure if I answered her or simply nodded. Then she said, "Well, that was nice. Now try this". Margie then proceeded to pull my face to her chest, and directed my mouth towards her left nipple. YES! I'M SUCKING HER TIT! My best day just got better!

Suddenly, she pushed me away from her breast and asked, "Do you know what is going to happen?" I was confused and stunned by her interruption and nodded my head, unsure of what she meant, but hopeful of what I wished. Then she asked me, "Have you ever done this before?"

Now the moment of truth was upon me and I looked away from her. I shook my head, embarrassed of my situation when Margie placed both hands on the sides of my face, looked me square in the eyes and said, "You really are a sweet young man and I really want us to continue. We both know that this is wrong, but I really want you and I want to make sure YOU really want this to happen". She continued, "And, your first time should be special so if you'd rather wait, we need to stop and I'll understand. I will completely understand". Her voice seemed to break as she said those last words before she leaned up and kissed my cheek.

Now I was a complete mental wreck. She started all of this and now she was playing the "moral" card. Crap! Being a young man of 18 and in THAT situation, I'm not sure I could have made two plus two equal four, but all I could think about was continuing what I felt as love for the first time. I think she could see my mind going in every direction possible while she studied my face for a moment and said, "Listen, if you're sure about this then kiss me, otherwise, we really should stop". Her eyes actually seemed to water a little and I can still remember the sound of blood pounding in my ears. I can't remember if I paused or not, but I do recall lowering my face to hers, watching her eyes follow mine before they closed and we locked our lips once again sealing our destiny.

I knew right then that life, as I had known it, would be different from then on. After a minute, I broke the kiss and, using all the knowledge I could muster from what I had read in the magazines, started working my way across her cheek to nibble her ear then down to her neck, hoping I would find an erogenous zone and praying I wouldn't screw something up. Margie was moaning, holding me tight as my kisses ran lower over her chest when she finally pulled my mouth to her breast and groaned.

She was giving me silent instructions, as she directed me from one nipple to the other when I first noticed that she was rubbing herself against me. Looking back, I am sure she had been doing it all along, but all of this was new to me and way beyond what my virgin brain could comprehend at one time. It was sometime during this kiss that 'I felt it'. Margie had run her hand between us and I could feel her touching me "down there". I must have frozen or stopped sucking because she asked me if I was okay. At this point I was well on my way to "becoming premature" in my pants, but nodded and told her "Uh...Sure".

So, I went back to 'nursing' as she rubbed against me with the flat part of her hand. She was holding my head to her breast, kissing the top of my head, grinding against my leg, and moaning all at the same time while I was taking turns feasting on her nipples. I was fascinated with them and loved the way they would crinkle and get hard in my mouth. Just then, I thought of a "lactating/nursing story" I had read in one of the magazine forums. That thought, combined with her rubbing and my sucking was enough to make me loose it. I grabbed her arm and held her hand still. At first, Margie seemed startled but she held still then smiled at me, once again almost giggling at my condition and said, "I'm not laughing at you. It's just... you're so cute and you're trying so hard. Just relax and enjoy this. Now what I'd like to do is to get a real feel of this".

Since I had no experience, I was not exactly sure what she meant, but right then I would have probably shoved my dick in a light socket had she asked. I watched as she raised her hand up to the button on my jeans and snapped it open. I looked up to her face and I suppose she had been studying me, watching my face for any change in my expression. As she slowly unzipped me, I felt like she was staring right through me, and just as she slid her hand over my underwear inside my jeans, she pulled me to her for another mind-blowing kiss.

Now there are moments in a young man's life that are monumental. My first bike, my broken arm, getting my learner's permit, my first car, my first kiss, but all of those paled in comparison to the feeling of Margie touching me there. Once again, I nearly exploded upon contact and she 'really' had not touched me yet. Thankfully, Margie's experience had taught her those indicators because she once again held still and told me to relax. She had her right arm around my neck and her left inside my pants as I rested on my left elbow with my arm under her and my right hand refusing to let go of her beautiful tit. Life was GREAT! We lightly kissed as things "calmed down".

After a minute or so, we were both still breathing heavy when she removed her hand from my jeans and reached over to unsnap her shorts. I watched anxiously as she slowly unzipped them, pulling them down to her hips and for the first time in my life I was looking at the top edge of a woman's panties. I cannot remember if they were a certain style or not, but I do remember that they appeared to be silky, 'baby blue', and looked like heaven.

She then reached back up and started tugging those beautiful panties down a little allowing me to see the start of her pubic mound. Now remember, this was back in the 70's and while I am sure women trimmed down there for wearing a bikini and such, it was the norm to have a nice bush between the legs. It was the most beautiful thing I had ever seen as I felt myself throb, I knew that 'this' wasn't going to last much longer.

Margie then took my hand that had been holding her breast and lowered it to her stomach right above her panty line. I instinctively knew what she was wanting, but being uncertain about how to go about it, I paused and she grabbed my arm by the wrist and slid my hand into her panties. WOW! Another monumental moment achieved as I slid my hand lower to cup my very first pussy. It started out as damp (as I had read) and the further I reached the moisture increased till she was soaked. Being my first time to touch a pussy, I was amazed that even her panties were wet. She moaned and hugged me tighter as she once again said those magic words: "Go ahead".

I was uncertain about what to do at this point so I simply gently started squeezing her mound and wiggling my fingers around until she started moving my hand up and down her pussy by my wrist. I do remember that while I was rubbing her I really wanted to locate the mystery hole between her legs but, not wanting to push my luck, I continued as she had shown. She must have been satisfied with my efforts because she let go of my wrist and returned to kissing me while slowly pushing my pants lower over my hips.

I finally got the hint and raised off the couch enough for her to push them over my hips. Not wanting to take a chance on being too forward, I did not return the favor until she raised her own hips and lowered her shorts and panties. I finally realized what she was doing and helped her when she got them around her knees and raised her legs up in the air to pull them off her feet. How could life get any better?

So now that all of the blood in my brain had long since headed south, I have Margie, shirt and bra open, naked from the waist down, lying on a couch with me and I'm completely lost as what to do next. Thank goodness she knew what she was doing. She returns to kissing me when I feel her take my cock in her hand and wrap her fingers around it. She starts rubbing my shaft up and down and once again I'm on the verge of making a mess when she lets go, grabs the waistband of my underwear and starts to tug them over my hips. I raise my hips again as she works them down to my thighs. I am unable to explain why I did not fully undress right then; I will have to chalk it up to nerves, inexperience or (probably) both.

As we once again embrace to kiss, Margie starts stroking my bare cock as I use my fingers to explore her pussy. Without her shorts in the way, I am now able to explore her womanly wonders freely. I find my treasure between her legs and my mind is racing at all the sensations my body is now experiencing. After a moment, she starts pulling my cock towards her and begins to rub it on the back of my hand. I instinctively pull my hand away as she scoots closer to me, pulls us together and begins rubbing my cock against her pussy. Oh, so this is how life gets better!

I wish I could sit here and tell you that Margie was dragging my 9-inch cock along the lips of her pussy, but actually I am only average size at 6 inches with average girth, so I am sure I was slightly smaller then. However, as she rubs the head of my dick against her pussy, she moans and comments on what a nice cock I have for a young man. That statement struck me as odd, but in reflection, I was so much taller than Charles back then, that I guess I was larger, maybe longer than him in that department.

I can only imagine her thoughts at my clumsiness in attempting to loose my virginal status, but thankfully, she was a sweet and patient woman who was willing to allow me to explore her body as I wished. I had read many stories and articles in the magazines I borrowed from the "library" and wanted to try them all, but right then all I could concentrate on was what my hands had explored and what her pussy felt like on the head of my dick. I am not sure I was even kissing her. We were lip to lip, but a rookie can only keep up with just so many things at one time.

So here I am, ready for what appears to be the final event. I break away from her lips and start to push my pants and underwear off my legs while she's pulling at my shirt. She tells me to stand up and swings her legs around to sit on the couch in front of me. I kicked off my shoes and she starts to lower my pants and underwear down and off my feet. She is looking up at me as I pull my shirt over my head and looking down at her, she seemed to have a cloud surrounding her.

For the life of me, I cannot even remember the color of the couch. I was totally lost in the vision of this woman. Of my Margie. As I stood there she slowly extended her arms up my chest and started sliding her hands down over my nipples, over my torso, till she came to my cock and took it in her left hand. She was so close that I can still remember the feel of her breath on my skin. She held my dick for a moment and then started lightly stroking me while looking up at me, telling me once again "You have such a beautiful cock". She dropped her eyes to my dick and started to lean in towards me and all I could do was stand there and watch. I was frozen to the spot as I just knew I was about to get my first blow job when she pulled it aside, and kissed me right above the waistline, below my navel. She then looked up at me as she brought her right hand up and cupped my balls gently caressing them.

I dropped my shirt to the floor, knowing what I wanted to do, but not knowing exactly what to do next. I definitely wanted to see her as naked as I was, but I must have hesitated as I reached for her blouse. She leaned towards me again and uttered those special words that I will never forget, "Go ahead".

To be continued...?

Note: Again, this is my first EVER attempt at/continuation of writing. I hope I haven't let any of you down as these events actually happened to me. I am trying to put them into my own words while embellishing for a more erotic appeal. I do not claim to be a writer of erotica, but I find the memories just as vivid as if it happened yesterday. I did not have this edited by anyone, as once again, I wanted the words to be mine. I hope you enjoyed it and while I encourage constructive criticism, your comments will decide whether or not I continue to post the rest of the story. Thanks for reading.

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SomewhereInMyPastSomewhereInMyPastabout 10 years agoAuthor
Chap 3

It is written and waiting for Literotica to approve. Again, thanks for taking the time to read my stories and post words of encouragement. I hope you enjoy the next chapter.

AnonymousAnonymousabout 10 years ago
Going well

If only my first time had been with a mature woman - but your descriptions brought back many memories. As the title says - go ahead. Your story is well written.

AnonymousAnonymousabout 10 years ago
Another Great Chapter

Thank You! I look forward to the next chapter.

oldnornryoldnornryabout 10 years ago
Lovely story.

T suspense is perfect.. Everybody remembers their first time And I was thinking of mine while reading. Great read.

TigerladyandhimTigerladyandhimabout 10 years ago
Delightful

What a lovely story, very erotic and amusing.

If only our first times,,, Oh well.

Love to read more from you

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Go Ahead Previous Part
Go Ahead Series Info

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