Gloria: First Time

by Dapper Dan

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, First, Oral Sex, Masturbation, Petting, Exhibitionism, .

Desc: Erotica Sex Story: Do you remember your first time. Gloria tells us about her first time: her first real love and her first time to "go all the way." She doesn't mind sharing that experience with you.

[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies, and as such, may or may not be completely realistic. All places, events, and persons, are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental.]


"Yikes!" I croaked out as I thought, it's five-twenty-five and Jack is due to pick me up at five-thirty! I did a quick look in the mirror. At least my face was on straight. The year was 1958, Saturday, March 29th to be exact, and this was to be our first date.

I'd invited Jack to the annual GAA (Girls Athletic Association) banquet. This was, of course, long before the passage of Title IX legislation in 1972, and girls were far from an equal footing with guys in sports. We girls had to be content with the GAA organization, an in-school games organization for girls with games between our own teams just for the fun of it. And that was only if and when we could find gym time between boys games.

Jack and I were seniors in our small town high school with eighty-five of us scheduled to graduate in little more than a month. My eighteenth birthday had occurred back in January just after Christmas vacation ended. Jack's eighteenth birthday would take place in three days, of all things, on Tuesday April 1, "April Fool's Day."

Like many small towns, Jack and I had been classmates since the first grade, but we never had a personal interest in each other until this night. Oh, we shared membership in a number of school organizations, band, science club, library club, drama club, and so on, but we never got really personal, much less dated.

My dates were mostly with older, out-of-town boys who appeared to be much more mature than the younger boys in my class. Jack had dated one or two underclassmen girls, but I don't think he was overly successful, whatever that means.

I was currently unattached and Jack, well, Jack was too and I think he had been for some time. He was kind of cute, in a shy sort of way. My thought was he might be fun to date a time or two. I was still a virgin, barely, and Jack? Well, unless I missed my guess, Jack was so much a virgin he was still wet behind the ears. As I said, this could be fun.

I heard the mantle clock strike the half-hour and then the ring of the doorbell. Jack, right on time. We'd agreed to ride around for ten minutes or so to get a bit more acquainted, personally, before going to the high school and the six-thirty banquet in the school cafeteria, the usual place such banquets were held. The School cooks did the honors in the kitchen. It was a lot different than the way it's done today.

Jack stepped into the living room at my invitation and I introduced him to my mother and father, much to his embarrassment. Dad shook Jacks hand with a hard squeeze, just to tease him. Jack exchange a few pleasantries with my parents before we quickly retreated back out the door, but not before the obligatory pictures in our prom clothes.

We were followed with the sound of mother's, "Enjoy the evening, kids!"

Jack's two-door hardtop, '57 Chevy sat in our driveway, reflecting the late evening sun off its highly polished, two-tone black and white surface. It was a gorgeous car what with its twin rear radio aerials, flashy wheel covers, dual exhausts, and blood red and black interior.

Jack opened the door for me and carefully closed it after I was seated, taking care to see that my skirt was tucked in and safe. Jack turned the dash mounted key and fired up. I may be a girl, but I could and did still appreciate the throaty V-8 engine growl exiting those duals.

Shifting into reverse with the manual floor shifter, Jack carefully backed out into the street and eased away, light on the accelerator. As we drew further away from my house, I slid over that big bench seat to snuggle up against Jack and felt his right arm drop around my shoulders. Maneuvering that floor shifter with my legs straddling it and my skirt fluffed out with three crinolines, was going to be an interesting exercise, for both of us, maybe a little fun as well!

Well, at least we're off to a good start, he's not totally bashful.

Just then Jack said, "Gee, Gloria, you sure look especially nice tonight, really special."

My, an even better start! I thanked Jack and said in reply, "You don't look so bad yourself!" I snuggled even closer.

Jack squeezed my shoulder as we made a quick trip down the main drag of town. We cruised around, looking for other couples while we chatted about various topics. Then we headed back out to the high school. He had to remove his arm from around me most of the time as he constantly had to shift the manual transmission. He was a bit embarrassed about having to fumble around beneath my skirt to find the gearshift.

"Jack, should I pull my skirts up out of the way so you can find the shifter better?" I just had to tease him a bit.

"Uh, ah, whatever."

So, I hiked my skirts up, exposing a great deal of leg."

I could see Jack blushing as he tried not to look--too often. The short ride to the other side of town to the high school was made in companionable silence as we enjoyed each other's company.

I hadn't expected this to happen, at least not so soon and was very pleased with the developing relationship. I reached up with my left hand and took hold of Jack's hand, which happened to be on my shoulder at that moment. I brought it down to rest on my right breast. Jack responded with a light squeeze and left his hand resting lightly in place. I sat there thinking delicious thoughts with my nipples about to burn holes in my brassiere. Yes, we used the full name for boob halters back then.

All too soon, we arrived at the school parking lot and Jack had to remove his hand and arm to once again engage action with the gearshift. We had to park quite away off and Jack offered to drop me at the door first.

"No, I will walk with you."

It was a fair hike, but I had a firm hold on Jack's arm which I tucked tightly up against my left breast as we walked to the door. I could feel the warmth of Jack's arm through his shirt and suite coat as well as through my dress and brassiere. It really felt good and I could readily see my effect on Jack.

His face was flush and his pants front was tenting out more than just a bit. The long walk and possibly thinking other thoughts probably accounted for the fact, that by the time we got to the front door, the tent considerably diminished. I was quite pleased with myself that I had that effect on him.

Again, by custom at our school, sophomore boys met us at the entrance to the cafeteria and escorted us to our reserved seats for our meal. More sophomores, this time girls, who were not in not in GAA, served the meal. And what a meal it was, at least for a school cooked one. We began with a fruit cocktail (naturally, no liquor!) and then a salad.

Conversation, which to this point was still buzzing rather loudly, suddenly began to die down to next to nothing from table to table as the entree was served. We had a good piece of round steak. Sorry, on the school budget, no T-Bones. There was also a baked potato, French cut green beans, creamed corn, along with milk, coffee or iced tea and water. Dessert was pineapple upside down cake topped with whipped cream, and more coffee or iced tea.

This was the first year that we girls had decided to hold a record hop after the meal. As the meal wound down, couples began to gather in the gym that was undecorated, save for a backdrop around the record table and another around the punch table. Elvis' Love Me Tender was playing. Jack took me in his arms and danced me out onto the floor.

I snuggled up close and tight, my breasts crushing into Jack's chest and my mons squarely on Jack's quickly rising boner. With an embarrassed reddening of his face, Jack reflexively jerked back. But I quickly slipped my left hand from his and dropped it to his butt. I pulled him back tight against my tingling mound of Venus and held him there. I guess I just was in a teasing mood.

I could feel the heat coming off Jack and I could see his flushed face. I was now even more sure that Jack was very inexperienced and shy, at least concerning physical contact with a female, and I was feeling horny enough to act rather more boldly than perhaps I would have otherwise. It was just fun to tease Jack a little.

As the record ended, Jack said to me, "I really need some of that punch, OK?"

"Sure," I grinned, "I need to cool off too!"

Except for the fast songs Jack couldn't and wouldn't dance, we danced all the slower songs and ballads, holding each other nice and tight, chest to groin. I don't think Jack lost his boner all evening. Poor guy! Poor me, for that matter. Both of us hot and bothered and not able to do anything about it.

My panties were wet all night and making me hornier and hornier along with it. I was surprised Jack couldn't smell my arousal. For that matter, maybe he did. I know he was perpetually red faced, but he never backed off again when I pushed my pussy up tight against his boner. In fact, it was not very far into the evening before Jack began making short, dry humping motions with his pelvis, a motion I eagerly returned.

Yeah, I know, it was a first date and all, but, hey, we both were nearly drowning in teenage hormones. I learned quite early that I possessed a really strong sex drive though I'd not yet "gone all the way."

Finally, Jack said, "Are you ready to get out of here?"

"Sure," I answered him, with a knowing smile.

We walked to the front hall door and Jack then said, "Wait here, I'll go get the car and pick you up."

As he walked off, I could see Jack was using his left hand to make adjustments to the front of his pants. No wonder he wanted to go get the car by himself; he must be pretty shook up and he's still sporting that magnificent boner!

A few minutes later, Jack pulled up beside me, in a grumble of duals and hot mufflers. He got out to open my door for me. I slid into the middle of the seat as Jack closed the door and walked back around to his side. As we drove off, I slid up tight against Jack's side.

"Jack, let's go to Highline Drive along the river,"

"Ok," was Jack's laconic reply.

He seemed preoccupied in his thoughts. His right arm was around me again when he was not shifting, and again, I reached up and pulled his hand down on to my right breast. Only this time, his squeeze did not let up as he held on tight, really tight. My dress was also hiked up again so he could shift--or whatever.

"If you're going to do that with that right hand," I said, "then do it under my dress and brassiere, it hurts too much through the clothes."

I heard a swallow and gulp as Jack's hand rose and dipped under my low neckline and into my brassiere to squeeze onto my bare boob. That hand felt red hot. We almost missed the turn to the road that led up onto the high river bluff of Highline Drive. Jack's concentration was divided and his last minute, one-handed turning of the wheel was awkward, but we made it.

Even so, Jack had to drop his hand back to the gearshift as we made the corner because he had to down shift to make the steep climb to the top of the bluff. Once up on top, we found a convenient pull off looking out over the river and the city skyline beyond it. Jack left the car in gear and then turned off the engine.

"Phew," he gasped, his face flush and shiny with a thin sheen of sweat and his hands now both on the wheel.

Jack sat there in silence for a few moments, until I leaned into him and began kissing his ear and on down his jaw and neck over to his chin. Jack turned and found my mouth with his.

Sparks flew between us as my mouth opened to his probing tongue and then my tongue met his in a twisting rock and roll dance. I dropped a hand to his thigh and his left hand came back to rest on my right boob, but on top of the dress. Jack broke our kiss and just hugged me tightly and for a considerable time. My hand brushed his prominent boner.

Jack broke the clinch with another, "Phew!" The he said, "Gloria, I need to slow this down here. My head is reeling and my thoughts are going places I'm not sure I'm ready to go yet."

"That's Ok Jack, really it is," I responded. Then I took the lead again when I asked, "You told me your birthday is next Tuesday, the first, right?"

"Yes."

"Ok, then, will you take me out Friday night and let me help you celebrate that birthday? I mean, I assume you can't go out on a school night anymore than I can."

"I would love to take you out again on Friday, Gloria," was Jack's enthusiastic reply.

"It's been such a lovely evening that I hate to see it end. But, it's one o'clock. and I'd better be gettin' home pretty soon, Jack."

Jack was just reaching for the key to start the car when a loud knocking banged on the his lightly steamed window. He rolled it part way down.

"Don't you damned kids know there's no necking allowed here after midnight?"

The guy didn't have on a uniform. He was obviously some self appointed, resident watch dog.

Jack cooly responded in a calm voice, "Isn't this a public road and a public look out spot? There aren't any posted signs saying 'no necking' that I can see."

"Smart ass aren't you sonny! If you don't get your sorry asses out of here, I'll call the cops."

"Fine, and my lawyer will deal with you in court then."

The guy fumed and growled, but he turned on his heal and walked off. Jack waited a couple of minutes.

"I guess we really ought to get going now."

"Yeah, I guess you're right, Gloria," he said as he started the Chevy.

Jack drove me home and I stayed snuggled up as tight as possible against him the whole, all too short trip--some thirty minutes. At my door, Jack took my hand and kissed it saying, "It's been a more lovely evening for me that you can ever imagine."

I replied, "Me too, Jack!" I grabbed him and locked my lips to his in a passionate, open mouthed kiss. When we finally broke the kiss, I said, "See you in school Monday." I quickly slipped through the door, into the house.

School the next week was a daze. What had started for me as a one or two time, teasing and fun date, had turned into something else. By the end of that date, and confirmed throughout the next week was the simple fact that Jack and I had fallen for each other.

Jack met me and walked me down the school halls whenever our schedules permitted and we even had the same class the last hour of the day. It was earlier during that class that I thought of and then asked Jack, to take me to the GAA banquet. It was an English lit class that both Jack and I loved.

Quite a few of our classmates were surprised that Jack and I became an item, a couple, and a lot of the girls in PE asked me about him. Jack, after all, was a pretty good looking guy, much more so than the "cute" I had first thought.

He wasn't out for any sport and never was all through high school, but he did participate in chorus, as well as both concert and marching band with me. As I began to see him in a different light, he was getting better looking and more desirable all the time.

That Friday night, Jack and I went to a movie. Jack had connections somehow and got tickets to what was then listed as an "arts" movie. The movie was Bridget Bardot in And God Created Woman! The movie was comical in the sense of a farce, but for all its pre-show hype about what Bardot was showing off, there was no actual nudity.

It was 1958 after all, so there was just innuendo and teasing. But nonetheless, the movie was highly erotic. Jack had his arm around me again and I think he was toying with a boner just from watching Bridget. But he got a definite boner once I reached up and again brought his hand to my boob, again, inside my low neckline and under my skimpy brassiere.

That boner must have been awkward and painful as he made no pretense nor any move to hide his actions when he reached down with his free hand and made some not-so-subtle adjustments.

"Damn," he quietly whispered to me, "that hurt and had to be taken care of, forthwith!"

I was surprised that he'd say anything but my mind was distracted when Jack's finger and thumb began to tweak the nipple of my boob. Both nipples went erect in a flash and when my nipples erect, they erect! They jumped out against my brassiere, setting off a fire in my boobs that traveled inward and downward towards my nether regions.

Movement of Jack's fingers was severely restricted by my brassiere, so I said, "Let me help a sec', Jack. Take your arm away for just a minute."

I reached in under my neckline and unhooked the front closing of my brassiere. I pushed the cups off to each side and said, "Ok, Jack, now you can go back to what you were doing, but share and share alike. Do them both."

Jack grinned while he leaned into me and kissed me on the cheek and then nuzzled me behind my earlobe which he also nipped lightly with his teeth before he resumed his nipple playing. God, did his hand feel good doing that.

I was so damned aroused by the time we left the theater that I hardly knew which end was up and staggered some as I walked beside Jack to the car. When we got up on Highline Drive again, and well before midnight, I dropped my dress top and thus bared my brassiere free boobs with the words, "Kiss them Jack, kiss them good and suck on them."

Jack bent to the task with relish and raised my arousal several more notches. I had my hand on his clothed boner by then massaged it. Jack was really working on my boobs with his tongue and mouth. Suddenly, Jack grabbed me tight and jerked.

"Oh God," he said, "I just came in my pants. Sorry, I'm so horny, I just couldn't help it!"

The wet spot had soaked through his underwear and was spreading out in his trousers. He must have released a real load that time.

"It's Ok, Jack, my panties have been soaking ever since the movie started. Welcome to the party!"

We kissed and played around some more for some time before Jack called a halt.

"We'd best quit this, Gloria, before this goes too far."

"Maybe I want it to go too far,"

"Maybe I do too, but I don't think that's too good an idea, especially since I don't have any rubbers with me."

"Maybe you should come prepared after this."

"Maybe, but for now, I'd better get you home before I change my mind. And you'd better put yourself back together. I don't think I could keep the car on the road if you don't."

So, before I snuggled back up to him, Jack watched me pick up my brassiere and drop in on the back seat, then pull my dress top back up where it belonged.

"You can keep that boob halter as a souvenir, Jack."

"Damn," Jack said, "I could look at those marvelous mounds all day and all night."

"They are pretty nice, aren't they, Jack. I'm a 34B and I don't think they're done growing yet."

"Well, all I know is, they taste and feel so damned good I can hardly stand to turn loose of 'em."

Then Jack's jaw really did drop as I raised my butt off the seat, hiked up my skirt some and reached for my panties. I slid them down and off as I watched Jack drool.

"Here," I said as I handed them to him, "another souvenir of our date tonight."

Jack couldn't help himself, he raised the panties to his nose and inhaled deeply. He about fainted. In a daze, he tucked the panties down the front of his pants. He then reached for the key and fired up the Chevy. We slowly drove off towards the highway and home.

Once again we had arrived at my door and we parted with another fiery and passionate kiss. Jack had both hands on my ass and pulled me tight into his boner. Sans my panties, my dripping pussy dribbled down my inner thighs, the pungent smell of my arousal drifting up between us. I bet Jack had one hell of a case of blue balls, again!

We dated all through April and May, every Friday and Saturday night and often Sunday as well. We couldn't keep our hands off each other, but neither did we find the courage to "go all the way." We never got totally naked either.

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