Gloria: Second Time Around

by Dapper Dan

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

Desc: Romantic Sex Story: Due to the request of the hopeless romantics in my fan base, I have posted this alternative ending and subsequent entirely new chapter to the original, GLORIA: FIRST TIME. Earlier in the original story, at the age of 68, Gloria goes back to her 50th class reunion and reconnects with Jack.


"Love is better, the second time around," or so the song says. I wonder.

Jack and I broke up shortly after the start of the first semester of college in the fall after our graduation from high school. I went to a school on the West Coast and made a career there while remaining single into my forties. He went to a school on the East Coast, got a job, married, and raised a family.

Jack's parting words were, "Gloria, you've been very special to me and you'll always hold a special place in my heart. I'm sorry we have to part like this, but so be it."

I married late to a man with a well paid but high stress job. That gave us twenty years before he died of a heart attack. We had no children. At sixty-five, I found myself financially quite well off, but widowed and alone. For three years, I enjoyed retirement and mourned my dead husband. Then came my fiftieth class reunion.

My home town and high school was in the heartland--central Indiana. I flew back, arriving at the nearby regional airport just after noon that Friday. I rented a car and drove the ten miles to Centerville to check into the motel room I 'd reserved. I quickly checked in and then rode the elevator to my third floor room.

I turned the hall corner and found my room. Another gentleman was unlocking his room door, but I was concentrating on my own door, so paid him little attention. That was a mistake.


The voice was somewhat different, but immediately recognizable.


"My God, it IS you, Gloria. What's it been, forty years at the tenth reunion that I last saw you?"

"Yes, and you didn't even speak to me at that reunion."

"Yeah, I know. Still too emotionally caught up with our past relationship, I guess."

"Your wife with you, Jack?"

"No, she died five years ago. Cancer."

"Oh, I'm sorry, Jack, I didn't know."

"Thank you. I'm pretty much back together again now. I wasn't for a while."

"My husband died three years ago of a heart attack. Job stress related, I guess."

"I'm sorry too, Gloria."

"So, Jack, going to the casual pizza party tonight at Giovanni's?"

"Yeah, thought I'd take that in."

"I could use an escort. Care for the job, Jack?"

"If you twist my arm, I might."

"Consider it twisted, very tight!"

A smile lit both our faces--and our eyes.

"We've got three hours. I need a nap, so call for me at five, Jack."

"Consider it done, Gloria."

With another smile, I stepped into my room and closed the door. The first thing I noticed was Jack and I were, by coincidence, given connecting rooms. I'd bet he won't miss that fact for long either. Interesting. I didn't even check the connecting door lock. I just stripped and stretched out on the bed. I was quickly asleep.

I awoke, mostly refreshed at four. Getting up, I ambled over to the vanity area across from the door to the bath and stool. My naked body stared back at me from the mirror. For an old dame of sixty-eight, not too damned bad. My boobs, never really big in the first place, didn't have too much sag as a result. More wrinkles than fifty years ago, broader of beam as well. The face staring at me had weathered some and was more angular than the high school senior one I remembered. All in all, not too damned bad.

Other than totally bald and a fair bit heavier, I wondered how else Jack had weather the four decades since I'd last seen him. Maybe I'd find out before the weekend was over.

God, my heart was hammering like a teenager's again.

The hour flew by as I showered and got ready for the evening. I'd just put the finishing touches to myself when the knock came on the hall way door precisely at five o'clock. My heart was racing again.

God, woman, you're sixty-eight years old. Calm down.

Jack was beaming at me when I opened the door.

"Your limo, Miss, awaits."

I took Jack's offered arm and he escorted me to the motel parking lot and stopped at the passenger door of a 1955 Pontiac Star Chief, Catalina coupe. That's a two door hardtop of that era. Top of the line for Pontiac and their first V-8 that was more than the equal of the 1955 Chevy V-8 that was also new that year.

The car was absolutely gorgeous. It was bright yellow on the front end and below the belt line to the rear bumper. The top and above the belt line back to the rear bumper was white. The two tone interior matched with a black steering wheel. The car also had the dual range hydromatic of that age, with the shifter on the column. That was quite different from the floor shifter of the '57 Chevy Jack had when we dated in high school. But more fun back then, him fumbling with that shifter between my legs.

"God, Jack, it's beautiful."

"Thanks. I got it this summer. Frame off restoration from the ground up. I bought it after the resto. It cost me a bundle, but I really wanted one. I'd been looking a long time."

I got in after Jack opened the door for me...

"No full skirt and crinolines to tuck in this time, Gloria."

"Thank God, Jack, thank God. Today's slacks and tops are so much easier on a girl."

The drive to Giovanni's would be about fifteen or twenty minutes. I slid over to snuggle up against Jack and his arm automatically went around my shoulder. The hand stayed on my shoulder, but I reached up and brought it down onto my right boob. He left the hand rest there without movement.

"Remember when we used to go to Giovanni's when we were dating, Jack? We spent many an after movie date there."

"Yes, Gloria, I remember quite well."

"Do you remember the senior prom, Jack and our motel room later?"

"Silly question, Gloria. I very damned well remember the night I lost my virginity."

"Mine too, Jack. We've got a motel room again, in case you hadn't noticed."

"I couldn't miss the connecting door, Gloria."

"Well Jack, my side won't be locked tonight."

It was at that point that we pulled into Giovanni's and Jack had to look for a parking slot. The lot was nearly full, so it took a bit to get parked. Jack didn't comment on my last statement.

We entered the Pizzeria and stepped into a sea of noise. Giovanni's was still a popular place and the new, much larger restaurant was full to the seams--hence the noise. We drifted through to the private banquet room where our class was meeting. Jack had taken hold of my hand back at the entrance. I guess I maybe got my response to my statement about the unlocked door tonight.

Jack had to let go of my hand to navigate through the very noisy sea of our classmates and shake hands as the two of us together talked to everyone present. Better than half our eighty-five classmates showed up, most with a significant other, to use the politically correct term (which I hate). A lot of memories were revived as we visited with everyone.

We at last sat down together and got a pizza ordered along with a whiskey sour for Jack and a vodka and 7-up for me. Fifty years ago, it had to be soft drinks. Jack and I got further acquainted with our respective histories of the past fifty years while we ate.

I'm left handed while Jack is right handed, so, like I did when we dated, I sat on Jack's left so our elbows wouldn't clash at the table and elsewhere. When we sat down, my right hand dropped to Jack's thigh and remained there most of the time while we ate. Several times, my hand brushed the area of his pants fly, but no bulge was detectable. Hmmm.

We were almost finished with the pizza when a buddy, "Speedy" one of the guys I ran around with in school stopped beside me. We hadn't seen him yet that evening.

"Well, Jack, I see the two of you got back together tonight. Is that reconnection going to last all through the night?"

"None of your business, Speedy, but we're of age now and both single."

"Oh Ho, the plot thickens."

"Maybe and maybe not, old man. How're things with you, Speedy?"

Jack and Speedy talked for some time. I joined in with a comment from time to time, but mostly, I just left them to rehash old memories while I talked to Allison on my left. Although not really "girlfriends back then, we did know each other well. She also kidded me about reconnecting with Jack.

After three hours, the party wound down rapidly. Jack and I were among the last to leave. Once back in the Pontiac, I again snuggled up against him...

"Jack, take me up on Highline Drive again, like we did in high school."

He didn't say anything, but Jack turned the Pontiac in the right direction. When we got there, Jack shut down the engine in our old pull off area and we just sat there for a while, staring at the lights of the city across the river. My hand eventually dropped to his pants front, between his legs. No bulge, no, anything.

"What you're looking for, Gloria, isn't there. An erection, that is. Diabetes, high blood pressure, and prostate surgery took care of that. Sorta took a lot of the fun out of life."

"Oh, I'm sorry Jack, again, I didn't know."

"It's ok, Gloria, there's still a lot of fire in the furnace. I just have to find other ways to stoke those fires in me or a partner. And there are many other ways."

We sat there for quite a long time. I just left my hand inert on his thigh. We would talk for a while, then sit quiet again. No, we didn't make out like a pair of teenagers. We didn't make out at all. We didn't even kiss. The clock read well past midnight when we decided to call it a night and go back to the motel. After all, we didn't want to get chased off again, ha ha. Besides, the class had lots going on for the morrow.

Jack did lightly kiss me on the lips at my motel door. He said "Good night," walked over to his door, and disappeared inside his room. Well, that's not exactly what I expected to happen, that's for sure.

Deep in thought about myself and Jack, I slowly stripped for bed. Yes, sixty-eight years old and I still slept naked. But, back to Jack. What is he thinking? Is he interested in me again, or just being friendly and curious about the last fifty years? Will he come through that connecting door tonight? What really were my own feelings? Was I interested in him again? I stretched out on the bed on my back in some anxiety with such thoughts milling around in my head.


I woke up after several fitful hours of sleep to the bright light of dawn. My travel alarm read five-thirty. Jack hadn't come through the connecting door. Why? Did I come on to him too strong last night? Wasn't he really interested? Maybe his E.D. is why he didn't come to me. But, up on Highline Drive, he specifically said there were lots of other ways to "Stoke the fires". Did he still want to "Stoke those fires" with me?

God, I just realized I really had wanted him to come to my bed.

My morning toiletry quickly completed, I just as quickly dressed in a casual summer outfit and went down to the lobby for coffee and more thinking. I picked up a bagel and filled a coffee cup. I'd turned just halfway around to go to a table when I was interrupted.

"Good morning, Gloria. Sleep well?"


"Oh? Too much on your mind?"

"Yes, you."


I thought Jack said that rather tongue in cheek.

"You purposely stayed away last night, didn't you? Why?"

"Trying to decide."

"Trying to decide what?

"How I really feel about you at this stage of the game. After all, I've not seen you to talk with you at least, in fifty years. And you want me to jump right back in the sack with you."

"I thought we had MUTUAL feelings last night, that we had sort of reconnected."

"Like I said, I'm still trying to decide. Don't rush it, Gloria."

"Ok, Jack. I remember how you never were a fast mover when we first dated either. Will you take me out for breakfast?"

"Jumpin' right in there, aren't you, Gloria. But yes, I'll take you to breakfast."

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