Debby and I go back to sophomore year of college. At least I was a sophomore. She was a senior, but we were the same age because I had bummed around for a couple of years after high school.
I saw her across the room at my favorite hangout. She was hard to miss because she was standing with her roommate, Stacy. You can't overlook two pretty redheads together, especially when one of them is nearly six feet tall.
Debby looked short beside Stacy, but she was really average-sized at about 5-feet-5. And her hair was a bright copper compared with Stacy's darker, Irish setter red.
I made a beeline for the pair, introduced myself and began talking. Okay, I was hustling. And before I could decide whether to focus on Stacy or Debby, a guy walked up and slipped his arm around Stacy's waist and started talking with her like a close friend.
No problem. I focused on Debby, and she was worth the effort. Bubbly and brilliant is how I describe her, not to mention sexy. She was a competitive swimmer with all the good things that means in the way of sleek, toned perfection. We saw each other often for six months, handicapped by the fact that she attended school 90 miles away and neither of us had a car.
The distance affected our relationship for the worse, as well as her resistance to sex beyond a certain limit. The daughter of an Army officer and a classic southern belle, Debby was still a virgin at 20 and determined to remain one until her wedding night.
Fearful of losing control, Debby wouldn't let me put my hand inside her pants. Nor would she touch my bare dick. She explained her reasons and I had to accept her beliefs, but I found it intensely frustrating. We enjoyed making out and I spent a lot of time exploring her small, firm breasts with my hands and mouth. But that was all.
Debby and I made a great pair, but I started fooling around with girls who were closer to home and more willing. Eventually we broke up. But we remained friends even after she graduated and moved away. I could count on her for birthday and Christmas cards, and an occasional phone call.
Then when I was a senior Debby stopped to see me while driving cross-country. She called from the road, so I canceled my plans for the evening and waited at my apartment. Boy did I get a pleasant surprise!
Debby more than returned my welcoming hug, then initiated a deep kiss that went on and on. My pulse -- and my dick -- were throbbing. Next I felt her hand stroking my erection through my jeans.
"Hey, what's going on!" I laughed, breaking the kiss.
"I have a big surprise for you," she grinned, leading me towards the bedroom.
Once there she opened my jeans and pulled out my dick! Debby stared down at it for a moment, stroking me lightly. Then she looked intently in my eyes.
"I'm not a virgin anymore," she said, "and once I crossed that line I started to wonder what I missed with you. So ... do you still want me?"
My answer was to take her in my arms and resume our passionate kiss. She still had a lot to learn, but giving up her virginity seemed to release all of Debby's inhibitions. We fucked into the wee hours, eagerly trying new tricks and positions while I introduced her to the concept of multiple orgasms.
Hunger and thirst drove us to the kitchen at 3 a.m., then we fell asleep spooning naked. I awoke to find I had missed my first class, but I didn't mind as Debby pulled my face down to her chest.
"You used to drive me wild sucking my nipples," she whispered. "Do it again!"
We were both tired and sore, so we made love gently and slept for most of the morning before getting up for lunch and a much-needed shower.
That was the beginning of me and Debby as friends with benefits. We never lived in the same city, as her career took her to New York and mine took me to four different places around the country. But whenever our paths crossed, and she didn't have a boyfriend, we jumped eagerly back into each other's arms. Emotionally, we had a special comfort and trust with each other that led to long, intimate talks as we lay entangled after sex.
If Debby happened to be dating someone, she would let me know, and the sexual part of our friendship would be suspended. I was her "between boyfriends" boyfriend. She once bought me a plane ticket to NYC so I could escort her to her company's Christmas party, and fuck her breathless afterwards.
All that ended when both of us married within a year of each other. Unfortunately, her marriage ended in divorce after two years and mine was faltering after three. I won't get into my marital problems other than to say that it took me a long time to admit that I married the wrong girl, and even longer to correct my mistake.
Meanwhile, Debby and I hadn't seen each other in five years and had talked by phone only a couple of times. So I was delighted one night when my phone rang at work and she was on the line. It was a pleasure to talk freely with a woman after the cautious way I had to talk with my wife.
And after few minutes Debby revealed that she was not in New York, but at a hotel only a couple of miles away!
"Once a month, the CEO and the Regional Directors fly to your fair city for a face-to-face meeting," she said. "And the CEO always brings a few staff to shuffle documents and handle details.