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HomeBisexual Stories Becoming a Man, Part 4: First Love

Becoming a Man, Part 4: First Love

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My first time with a woman. And not just any woman, but my first true love.

After a couple of oral exchanges with guys, who went on to go out with the girls of their dreams, I ended up frustrated the rest of senior year. But after graduation I finally got to be with a woman. And not just any woman.

“If you want to hang out sometime this summer, give me a call."

I had graduated high school two weeks ago.  At the end of the very last graduation party, I was walking back to my car. Laura had come running up after me, handing me a slip of paper with her phone number on it.

“Okay.  That’d be great,” I stammered. After a slightly awkward pause: “Uh, yeah it would be nice … I mean, I’d like to see you before you go.”

She replied, “Cool.  I'll look forward to it.  I’m going to miss you next year,” and gave me a big hug.  I really liked Laura, even had a crush on her, and I can't say I minded her crushing those soft breasts up against me.

Since my previous stories, a lot had happened.  It was my senior year, after all.  Earlier in the year, I had managed to exchange blowjobs with my buddies Matt and then Ron.  As wonderful and free of entanglements as that had been, they were just about cock and sexual release.  I really wanted to get with a woman.  I did have a girlfriend for much of the spring - Taylor - but didn't get further than slipping my hand inside her bra cup and briefly touching her nipple.

I won't say more about my relationship with Taylor except that she proved to be a jealous, needy girlfriend. As a cruel parting gift when we broke up on graduation night, she said some really hurtful things that shattered my confidence.  Despite my pain, I could see that I was better off without her, but I would be a mess for a while.  

I was still in this state when, less then two weeks after the breakup, Laura gave me her phone number, basically begging me to ask her out.  As part of my inner circle of friends, Laura had had a front-row seat to Taylor's hysterics. Did she genuinely like me, or was she just doing this because she felt bad for me? Dumb me, not realizing both might be true.

I dragged my heels for a couple of weeks, wallowing in misery.  And then, in late June, I looked through my yearbook, reading through my friends' comments for the first time.

And there it was.  A mention from my friend Don about how much Laura had been "hanging around" me during senior year.  Thinking back, I realized it was true. Taylor had expressed extreme jealousy towards Laura. I now realized this one wasn't just a paranoid delusion: Laura indeed had spent a conspicuous amount of time around me - and I was the only person too clueless to notice.  Even more clueless was me just now realizing that two weeks ago, she had asked me out and I still did nothing.  I finally called her.

“I'm really glad you called, Joe.  I’d love to get together, but I have to go to the airport early in the morning.  My parents are taking me to New York for a week and a half.  I’ll be back on the Fourth of July.”

Somehow I managed to stammer, “Well, do you have plans for the Fourth?”

“No, I don’t.  But it would be fun to go see some fireworks with you.”

Now that was an explosive idea.  “Yeah, that would be great! When do you get back?”

“On the Fourth, silly!  I already told you that.”

“No, I mean what time do you get back?”

“Oh. My flight comes in at about 4.  I’ll call you as soon as we land, and we can figure out a plan. I can't wait, Joe.”

After all that anxiety and buildup, all it took was a three minute phone call to set up a date with Laura.  Laura!  I mean, she was easily on the list of top 10 girls I wished I could go out with - most of whom showed NO obvious interest in me.  

Hell, she WAS the list, if I weeded out those never-gonna-happens. Although I liked Laura mostly for her earthy and warm personality, her looks left nothing to be desired.  Well, better put, her looks were very much to be desired, at least by me.  She had a reasonably attractive face, and a really infectious, almost conspiratorial smile.  Creamy skin, periwinkle eyes, strawberry-blonde hair, never wore makeup.  She was also very tall, approaching six feet. She was moderately full-figured yet quite athletic, with nice round hips and shapely breasts. Not every guy's cup of tea, I suppose, but I found her captivating. And she was an infinitely better human than Taylor. 

When the day came, the weather was perfect.  Just a little warm, but not hot at all.  It was ideal for a picnic, so that’s what I planned.  We went to a lovely park with a waterfall, and had a great outdoor meal.  I’d even brought a chilled bottle of sparkling cider and some champagne glasses.  Laura, for her part, was wearing a sundress and looking spectacular.  Afterward, we went to the city to watch the big fireworks display, with a blanket to lay out under us and another to draw over us if we got cold.  I’d thought of everything, and somehow everything went perfectly.

As it was getting dark, she grabbed my hand and said, “Thanks for doing all this.  I’m having a really good time.”

“Me too.”  We were looking into each other’s eyes.  Should I kiss her now?  I hesitated for a moment, then we both leaned in and kissed on the lips.  

And the fireworks really started.

Unfortunately, I don't mean metaphorical, romantic kissing fireworks.  Those got rudely interrupted by the literal fireworks up in the air.  She broke our kiss, clapped her hands together and said, “Ooh, it’s starting.”

Well, I couldn’t complain.  The kiss was great.  The memory of her warm, soft, pale pink lips on mine lingered through the whole show.  She held my hand and snuggled up against me.  At the end, I leaned in for another kiss.  And felt that kiss lingering on my lips the whole drive back to her house.

I walked her to the door.  Both of us said what a good time we had, me asking her if we could get together again on Friday, her saying yes, me leaning in for the proverbial goodnight kiss.  We kissed a third time, now with our tongues.  She pulled back after a bit, then we said goodnight again and she went inside.

I couldn’t wait for Friday.  When it finally came, we went out for a cheap meal and then a movie, then back to her house to hang out and talk in the rec room.  Soon we kissed again, but this time it got more passionate.  Lying together on the sectional, our bodies pressed together, we made out for literally more than an hour. As this went on, she also started to grind her hips against mine.  I was hard enough to cut glass, and she was pressing against me so hard I think I actually felt her clitoris through the fabric.

I moved my hand to one of her breasts and started to massage it lightly. She moaned lightly.  Oh, the full softness of it was wonderful.  I couldn’t wait to get those babies out in the open and suck on them.

“Sorry, I’m not ready to do this tonight,” after half a minute of this.  Runner is out at second base!  Same exact spot where I'd been called out with Taylor, in fact. Oh well.

It had been an amazing evening so far, but it was well past midnight.  She explained that if we went any further she wanted it to be just right, and not starting at such a late hour.  She walked me out the door, and we made plans to make dinner and watch a movie at her house.  She flirtily said, “so we can get an earlier start tomorrow.”  She also explained that her parents were going to a party out of town and wouldn’t return until very late. 

We kissed deeply again for a couple more minutes, then she squeezed her breasts into my chest, shimmied them back and forth a couple of times, and seductively whispered in my ear, “These will be ready for you tomorrow night, if you’re good.”  I almost came in my pants.  I did come as soon as I got home to my bedroom. Three times. 

The next night we made pizza, playfully licking sauce off each other’s fingers, then watched a movie in the basement.

At least we started to watch a movie.  10 minutes in we were making out again, and Laura was dry-humping me as hard as the night before.  This time she took hold of my hand and pulled it to her breasts.  I started massaging and kneading these soft wonders gently, while Laura moaned lightly, and through her bra, I could fee the nipples harden under my touch.  I gently squeezed them, as she moaned more deeply.  

I moved away from her mouth and started to kiss behind her ears, then down the nape of her neck.  Meanwhile, I started unbuttoning her blouse, fumbling a bit this first time, but getting the job done.  Now I was facing the spectacular sight of a nice pair of breasts, deeply cleaved, straining against their lace prison.

“Let me help you with this.”  She reached back, undid the clasp of her bra and let it fall.

Here I was, viewing a woman's bare chest for the first time.  Voluptuous in their roundness, C-cups large enough to sway uneasily back and forth a bit, and as they hung down a bit to form a crease against her abdomen below. Pale blue veins slightly visible in the pale light of the television.  Hard, pale pink nipples, framed by generous pale wrinkly areolae dotted with follicles. I can describe the scene in such detail because it is forever burned into my retinas.

I had to pull my pelvis away from hers as my lips worked their way from her neck, down her chest, and back up the slope of one of her breasts.  I took one of the nipples into my mouth and sucked on it.  She sucked in her breath and stifled a squeal. “Oh my God that feels good.  Lick the other one too! Don’t stop!”  I got a rhythm going, going back and forth between her breasts while taking enough time to linger on each one.  She was really getting worked up, rubbing her pelvis hard against my side.

I moved one hand down that direction, asking, “May I?”

“Yes!”  So I started rubbing her mound through her pants, definitely feeling her hard clit now.

I moved my hand back up towards the top button.  “May I?”

“Yes!”  I undid the button and zipper, then started to pull off her pants as she lifted her hips to help.  Then I pulled down her panties and she lifted her hips to help with that.  She was naked now except for her socks.  And so, so beautiful.  Every part of her.  The curve of her hips.  Her long, smooth, athletic legs, now parted.  And between them, the most lovely blonde bush ever.  Slightly trimmed along the sides for swimsuit season, but otherwise full, the blonde hairs glinting in the glare from the track lighting at the other end of the room.

I went back to sucking and licking her breasts, and she went back to moaning.  My hand rubbed back and forth over her velvety triangle, and my fingers quickly found her erect clitoris hiding under its little hood.  I touched it gently and rubbed it a bit, making her squeal.  

“Keep doing that!”  I rubbed gently for a couple of minutes, then worked my fingers down towards her opening.  As with most guys' first time, it took a minute or two to figure out the layout down there.  I felt around the wrinkly labia for a moment until I found the actual juicy entrance.  “May I?”

“Oh yes!”  So I slowly slipped my middle finger in a bit, then back out, then in further until it was all the way in.  Soon she was riding it up and down, while I used the rest of my hand to rub her clit. 

But if you’ve read any of my other stories at all, you know I'm a relentlessly oral person.  Cock, tit, or pussy, I want to taste it, get it in my mouth.  I moved my mouth along the underside of her breast, to her belly, kissing her with my lips and tongue all the way, while continuing my handwork below.  I stuck my tongue playfully in her navel, provoking a giggly squeal, then sucked on the slight roundness of her belly and moved down towards her bush.  “May I?”

“Oh, you polite, sweet man, thank you for asking. Oh please yes, my God, YES!” I licked along the top edge of her triangle to the top end of her leg, then down along the side of her bush, finally sucking on the crease between her thigh and the center of the universe, jumping across to the other side. And then, finally, putting my face right in front of her womanhood.  Like everything else about her, it was beautiful.  

I took in the powerful scent.  It was simultaneously unlike anything I could have expected, and yet exactly what I expected. I stuck out my tongue and licked the outside of the labia, then traced my tongue around it, exploring its many folds. Laura was whimpering with pleasure, taking short breaths. I found the clitoris, swirled my tongue around it, then took it between my lips and sucked for a moment, prompting a long deep outcry.  I continued to work on her labia and clitoris alternately, using both my tongue and lips, and she started moaning loudly between each breath.  

Then her body tensed and started to shake, then in one instant broke out in a cold sweat as she screamed with pleasure.  She rode my face for a few more moments as she descended, finally catching her breath.

“Thank you.  That was amazing.”  I moved back up and she kissed me gently.  Then, tasting herself on my lips, she opened her mouth and kissed me hungrily, sucking the juices out of my mouth.

“We need to do something about these clothes.”  I couldn't argue there: I’d been so busy exploring her body that I was still fully clothed.  She pulled my shirt over my head, then started to kiss the nape of my neck, quickly working her way down my chest, sticking her tongue in my navel (prompting an equally playful, fake-feminine squeal from me), then sucked on the treasure trail below.  “May I?” she asked with a grin.

“Yes, Laura.” Like I’d say no to my first blowjob ... from a woman, that is.  I was quickly as naked as she was, and she squatted in front of me, herself getting a first closeup of the opposite sex's equipment.  

"It's so big!" I'm only average-sized, but I understood the sensation.  I'd had the same feeling when I'd gotten Matt's machinery in my face for the first time.  Then she looked me in the eyes, and without breaking eye contact,  gingerly touched her tongue to the head, picking up a few drops of precum.  “Ohhh,” I moaned.   Then she kissed it with her lips.  

She broke eye contact for a moment, making little kisses down the shaft, onto my balls, and back up the shaft, planting kisses all the way around the head.  Finally, she locked eyes with me again, smiled, opened her mouth, and slid it over the crown.  I moaned hard, and loudly.  She took it in as far as she could, then started pumping her mouth up and down, bless her heart.  

Her teeth touched it briefly, I made a mild unpleasant grunt, and she realized that teeth didn't feel so good, and it didn't happen again. After a few strokes, she took it in deep, gagged a little and backed off slightly.  She was a fast learner.  For a first time blowjob, and not being a guy who innately knew how it felt, she was doing great.  Then she cupped my balls in her hand, and that started pushing me towards the brink.  

I warned her I was about to cum, and that it would be a lot.

She pulled off just long enough to say, "Good.  I want to try it."  Well, that sent me all the way over. I shot a first powerful stream into her, followed by several more. I think one of the jets caught her off guard and went towards her windpipe, causing her to gag for a few seconds, turning red in the face.

"I'm sorry!  Are you ok?"

She nodded her head as she recovered her breath.  Then she looked up at me, with a naughty look in her eye, opened her mouth wide so I could see all the white goo in there, and swallowed it with a loud gulp.  As she moved back up on the couch next to me, she said, "Well, I won't make that mistake again."

I must have looked crestfallen, because she giggled and quickly said, "No, silly!  I just mean I won't gag next time."

She smiled that naughty smile again and said, "Don't, worry, you'll get more blowjobs from me."

And then added, "Maybe even tonight."

I was still coming down from my massive orgasm and hadn't said anything, but she giggled, "I don't know why some girls complaining about it.  That stuff doesn't taste bad at all.” 

“No, it doesn't.”  And I kissed her deeply while we wrapped our arms around each other and held our bodies together.

"So you've tasted it yourself? And it doesn't gross you out?”

"No. Tastes fine to me."

"Really?  Is that just because it's your own?"

"Doesn't matter. Tastes fine either way."

She snuggled up against me, clearly aroused by my answer, pressing her breasts up against my chest and her pelvis against my recovering member.  Which might have started to harden slightly at her interest in this topic.  

She delicately asked, "What does that mean, either way? Have you tasted another guy's ... you know ... stuff?" I gave a little smirk.  "I've heard stories about boys playing around."

"Yes, a couple times."

At this point we were rubbing our genitals together, my still-slimy rod rubbing around her vulva, right next to her slippery opening.  We were this close to the holy grail, and I think the growing urgency of this slipping and sliding pulled her out of her trance.

She backed away a little bit, looking a little more serious.  "Um, I'm just not quite ready for that right now.  Before we go any further I need to tell you some things about myself. I'm sorry."

"No need to be sorry.  That was so amazing.  If we stopped right now I'd still be in heaven.  I don't want to make you do anything you don't want to do."

Looking a bit relieved but still serious, she said, "Good.  Because that's, well, that's kind of what this is about."  

She told me about her previous summer, when she had worked as a counselor at a summer camp.  After the last campers had gone home at the end of the season, the counselors had all held a huge party.  Laura had a great first couple of hours, but while she stepped out for some fresh air one of the male counselors had dragged her out into the woods and raped her.

"So I'm just not ready to have you inside me yet. That first time was horrible, and painful, and violent. Please be patient with me. It's not that I don't want to, I'm just not ready."

I assured her that I felt terrible about what had happened, totally understood why she felt as she did, and that she would get absolutely no pressure from me.  Heck, she'd already told me I would get more blowjobs from me. How could I complain? 

I also said I'd noticed that she seemed out of sorts the first few weeks of the school year, but of course, I'd had no idea why.

She continued, crying a little, explaining how lucky she was that her friend Dorothy, her best friend since fourth grade, had been there for her.  Dorothy had also been at the party, and had been able to help Laura with the immediate aftermath, consoling her and helping her walk through her grief and pain the next couple of months.

"And by Halloween, I was starting to feel a lot better and ready to get on with my life, and even enjoyed myself at a party, but a couple guys there hit on me and it started bugging me. By the next week, I reverted to the Anger stage.  I was telling Dorothy how horrible I thought men could be and how repulsed I was by them.  Sorry, no offense, but that's how I felt."

"Definitely none taken."

"Anyway, I don't know if you noticed, but soon after that I kind of stopped hanging out with Dorothy for a while"

"Actually, I did notice that, but didn't think too much of it."

She beamed. "Ha, so you have been watching me!  I kind of thought you liked me, but you can be hard to read."

"I was too nervous to ask you out.  I really didn't think you'd go for a guy like me."

"Well, I'm glad finally cleared up that question by asking you out!"

She kissed me on the lips and snuggled in closer to me again.

“Okay, I'm done telling you about the bad stuff,” she said. “But I still want to tell you what went on between me and Dorothy."

She continued, ”So I was in this angry state about guys, and she was holding my hand to comfort me, and then she said, 'Well, maybe for you to heal guys aren't the answer right now'. 

"And she looked me in the eye in a way she hadn't done before. I mean, she didn't kiss me or touch me in a sexual way, and I'm not even sure she was about to. But I just sensed this sexual energy from her. I was so not ready for that, and afterwards I couldn't be around her for a few weeks. "

My member stiffened involuntarily at the thought, and she noticed.  "Sorry."

She smiled.  "It's OK.  I know you men are all hardwired to get excited about two women together. It's cute. Nothing ever happened between me and Dorothy, but ... "  

At this, she wrapped her hand around my cock.  "... sometimes I think it might have been good for me if it had.  I wasn't ready to be near a guy, but it's not like my hormones turned off.  Maybe it would have helped my healing. I think I would have enjoyed it."

I was fully erect now.  She gave me the same sexy smirk I'd seen a few times now, and asked, "What would you think if I'd leaned in and kissed her?  On the lips?" And she kissed me on the lips.  

The question was clearly rhetorical here - not looking for an actual answer.  "What if we started French kissing?"  And she opened her mouth and we played with each other's tongues for a few seconds.

"What if Dorothy took off my bra and touched my breasts?" She thrust out her chest a bit and pulled my hand up to it.  I eagerly obeyed this implied request and started slurping on them.

"Oh, I think I would have liked that a lot.  I think I would have liked to suck on her breasts too.  They look really nice."

I didn't doubt that for a second.  Dorothy was a spunky, sexy girl.  I had in my possession a photo I'd taken the past summer, when I was at a beach with a bunch of friends. Dorothy was in the foreground, lying sideways on a towel in a skimpy two-piece.  She was short, with olive skin and wavy brown hair, a beautiful round butt (I'm not an ass man, but I sure noticed hers), and very nice B-sized breasts showing substantial cleavage in that swimsuit.  I wasn't about to tell Laura this, but that photo had featured in a few excellent gherkin-jerkin' sessions by now.

"What if Dorothy touched me down here?"  And she pulled my hand down to her vulva.  It was clear what she wanted me to do, so I started rubbing, gradually working a finger, and then two, in there, as she started moaning and writhing a bit.  

"Oh Dorothy, I want to taste you."  With that, she pulled her groin away from my hand, shifted herself so her head was down by my hand, and started licking all of her juices off of it.  "Oh Dorothy, you taste so good. Will you lick me too?"

It seemed like she wanted to keep this role-play going, so I maneuvered myself in front of her pussy again and started licking.

"Oh yes! Dorothy!  Eat me!"

Then she sat up a bit and said, "Oh my God, it felt really good to get that out.  I didn't realize my fantasies about that were so strong.  Thanks for helping me with that."

"Uh, you're pretty damned welcome."

"But hang on a sec, here.  It's not so unusual for women to be flexible about their sexuality, but I don't know many guys that are.  You hinted at something a few minutes ago ... have you done something with another guy?" She could see the affirmative answer on my face,  looked at me with those beautiful deep blue eyes and begged, "Please, please, please tell me all about it."

I started telling her about my first same-sex encounter, with Matt at his apartment complex's hot tub.  She expressed amazement that sporty Matt, very popular with women, had a taste for dick, and she listened with absolutely rapt attention.  When I got past the setup to the part where we touched each other's penises in the hot tub, Laura reached down to touch mine, smiling and stroking it gently.  Then I told her how I eased myself off the ledge into the water and started sucking Matt, she said, "That is sooo hot" and she eased herself down the couch and started sucking me.

"Keep talking.  What happened next?" she asked as she looked up at me.

I described how we went back to his apartment and got into a 69, sucking each other's cocks in synchrony.  She rolled me sideways and onto my back, swinging herself around so she could lower that beautiful blonde-framed vagina of hers right onto my face.  

At this point, obviously, I had to pause telling my story.  

We worked on each other, both moaning passionately, and then she pulled her mouth off me and started moaning louder.  I kept licking and sucking down there, reaching up to cup her breasts and then roll her nipples around with my fingers, and that sent her over the top.  

She stiffened and shook in orgasm for quite a few seconds.  After she had calmed down a bit, she took me back in her mouth and I finished off with another rip-roaring ejaculation.

This time she didn't swallow.  She sat up, leaning back, and let my semen drip down her chin, running down her neck and onto her chest, some of it continuing down the valley of her tits.  "Will you eat cum for me and clean me up?"  I kissed her deeply, tasting my cum again, and worked my way down her torso, not missing a drop.

I hadn't even had a chance tonight to tell her about my encounter with Ron, though I later would.

The next couple of weeks we were inseparable, hanging out and doing all sorts of fun stuff together, going to an outdoor concert and a free museum, taking long bike rides, and canoeing together.  And we had about as much sexual fun as possible without my penis entering her vagina, although she let me rub it around the opening a lot, which got us both hot and bothered.  Sometimes it even slipped in an inch or so by accident, but I was always the one to pull back out. I was determined not to violate her trust, though the temptation was strong. Fortunately, she was on the Pill for medical reasons, so at least we didn't have to worry about her getting pregnant from this fucking around.

I think I was falling in love.  Maybe she was too.  And therein lay the problem. 

Our lives were about to go in very different directions.  She was going to go to Europe for a few years.  Not only that, but she would be spending the following summer over there, her parents going over to tour around Europe with her for most of the summer, so she wouldn't even be setting foot back here for at least two years, possibly longer.  I couldn't imagine not being with her, even though being with her would be impossible.  

I talked about staying in touch and writing lots of love letters back and forth while we were apart, and she became visibly uncomfortable.  She tried to put it delicately, but made it clear that we would no longer be together a month from now, and would have to make a clean break.  This summer we were having was going to be all we would have. There was no way we could continue the relationship once she got on that plane, no way she could have any entanglements.  We were about to start our lives anew, and we needed to not be bound to each other or anyone else.

Of course, she was right, but I had a hard time seeing it.  We started arguing - more tearfully (on both our parts) than angrily - but I just couldn't stand the thought.  She finally asked me to go home, and maybe we should spend a few days apart so we could think things over.

It was a week of agony.  Not only was I about to lose the woman I loved -- I'd already lost her!  It took a lot of depressive binge-listening to darkwave music, but I finally came out my funk clear-headed.  

What a fool I'd been!  Everything she'd said was right. Of course, I needed to start my new life in September as much as she did, and I needed to be free of tethers to my high-school life as much as she did.  And maybe I'd never find another woman as fantastic as her (which maybe in some respects, might turn out to be true).  

But even if that was true, what in the fuck was I doing, sitting at home alone, when maybe there's a chance I could still have 3 last weeks with her?  I finally got the courage to call her.

I told her how she'd been right and I'd been wrong.  I apologized for being possessive.  I told her that I loved her - not in the way that demanded we stay connected while we couldn't - but enough to set her (and myself) free.  I told her I couldn't imagine wasting the chance to spend time together while we could.

"Please come over, now," was her only reply.


This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than avataransk.ru with this note attached, it has been posted without my permission.

Copyright © Copyright (c) 2020: reproduction or distribution prohibited without specific consent of the author. Any resemblance to real people or events is purely coincidental. My stories depict sexual encounters between unrelated consenting, mutually affectionate adults, often of the same sex. DO NOT READ if such material offends you, or is illegal for you to read at your age in your jurisdiction. Otherwise, I hope you enjoy.

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