My First Time

A first time sex story: My First Time. Author: firstimewonder. The story is including: True Story, First Time sex, Male/Female sex. I knew that people had sex from mid high school days, but didn’t experience it until a few years later.

A first time sex story: My First Time

Author: firstimewonder

My mother had told me the basics, so I knew I could get pregnant, but the processes of accomplishing it were fairly vague. I entered a strict Church related college right after graduation from high school, so my education about sex was still some ways off.

During the second semester of my sophomore year, I met Dean. Actually, he was dating another girl while I was dating his roommate. Since his roommate didn’t have a car, Dean usually drove when we double dated. It was only a few weeks until I realized I was dating the wrong boy. I sensed that Dean felt the same way, but both of us respected the commitments to our partners. However; over the course of a month, Dean broke up with his girl friend for reasons that had nothing to do with me. Then when my boy friend began cheating on me when I was out of town, I broke off with him. Shortly after, I accepted a date with Dean.

Within a month we were engaged! Even though Dean had a reputation of being terribly shy, it wasn’t long before I realized I was going to have my hands full with him. He was respectful, but in his shy and inhibited way he made it clear that he wanted to know more about girls in general, and me in particular. Naturally, we cuddled and kissed as you would expect of a newly engaged couple, but before long he began running his hands up and down my back, and I could feel him exploring the outline of my bra. He paid special attention to the clasp, almost as if he were trying to learn how to unhook it through my blouse and slip.

We didn’t progress past a lot of kissing and general feeling of each other’s non-sexual body. Occasionally, Dean would accidentally bump my breast. I didn’t protest, because he wasn’t terribly aggressive about it, and besides, I kind of liked it! He asked to take me home about four hundred miles away to meet his family after school was out. Afterwards, I was coming back to my parent’s home on a bus while he spent the summer working for a farm supply business.

During the nine-hour drive to his home, the reality that we were going to be separated for three months began settling into my thoughts. Naturally I sat close beside him on the drive, and he had his arm around me most of the time. Presently, I became aware that he was becoming more aggressive about bumping my right breast. Before long he had his hand resting on the side of my breast doing little circles and massaging it gently. I didn’t protest, but cuddled closer to him offering my non-verbal assent. We talked of our separation, expressing our undying love as you might expect of young lovers.

I was to be at his parent’s home for a little less than a week before I returned home. Dean drove me all over his boyhood stomping grounds, taking me to the schools he attended and showing me the places where he had lived. In addition, he took me into all the farm buildings, sharing the places where he played as a child, and where he hid. One of the places I enjoyed was the huge barn and the hayloft. Dean showed me where he built caves and rooms in the bales of straw. We spent some time cuddling and kissing in one of the rooms he built to show me where he played as a child.

All too soon, it was the night before I was to leave. His parents went to bed early, probably to let us have the living room alone on my last night. We were sitting on the divan, and of course we began kissing and cuddling. Before long, we were lying side by side, stretched out together. We were locked in a passionate embrace, pressing together as if we were trying to exclude our clothes from inhibiting the feeling of our bodies together.

Dean said something about how nice it would be when we could love each other all the way, and how much he was looking forward to being able to sleep with me. I sighed, telling him how much I was looking forward to the same thing. We started talking about what it would be like, when Dean surprised me by asking if I would like to feel him. I agreed and seconds later, I heard the snap of his jeans pop open, and the zipper slide down. He took my hand and guided it beneath his shorts.

I had never seen an adult penis, certainly not an erect one, so had no idea what to expect. The first sensation was feeling the tip. What a puzzle, at first it was silky smooth and soft, but immediately below the surface it felt like a rock. I felt the tip, touching the ridge just below the cone shaped tip, then down to the loose skin on the main shaft. I was astounded at how big it felt. I wasn’t able to close my hand around its circumference! I continued feeling down the length of the thing, amazed at how long it was. Dean shifted his hips slightly providing me a little more room for my hand in its downward exploration trip.

I felt his pubic hair, then the place where the monster joined his body. Dean took my hand, guiding it further down to where the soft silky sac holding his balls was located. He told me to be very careful because his balls were quite tender. I had known that from having seen boys get hit on the playground at school so tried to be especially careful. It was obvious that he enjoyed the feeling of my hand a great deal. I was aware that his breathing was becoming rapid, and his body was about as rigid as his thing. After feeling his most intimate parts for several minutes, I sensed that I probably better stop, or there would be no stopping.

Dean asked if I would like to see it, but I said I didn’t want too just now. He zipped and buckled up, then kissed me gently telling me how much he loved me and was going to miss me. Dean had let me touch him, so I decided it was only fair to offer to reciprocate. I was keenly aware of how much he wanted to feel my breasts, and after all, his parents were in the bedroom just a few feet away, so I was sure things couldn’t get too far out of hand. I asked if he would like to feel my breast. His response was predictably immediate and positive. I unbuttoned my blouse and took his hand, guiding it under my bra.

It was obvious that it was not going to work very well with my bra fastened because there simply wasn’t enough room for my breast and his hand at the same time. I sat up for a moment and unhooked my bra. In an instant, his hand was on my breast, probing, feeling, rubbing and rolling my nipple between his fingers. The feeling was so exquisite that I could scarcely contain my feelings. His touch sent tingly feelings throughout my body, down to my tummy and into my bottom. It was so heavenly that I willed it to go on forever.

He stroked and massaged for several minutes, and finally pulled his hand back. By now, I was in such a state of arousal that I hardly believed it myself when I asked if he wanted to feel the rest of me. Predictably, he agreed without hesitation, and began stroking my bare tummy under my blouse. I was wearing slacks with a zipper down the side, so while he was playing with my tummy, I unbuttoned the band and slid the zipper down. Dean heard the zipper go down, and instantly moved his hand down toward my bottom.

I felt the tingly feeling in my tummy as he worked his hand down, down, down. Just as he encountered my hair, he stopped.

You have hair! I couldn’t resist the giggle that rose up.

What did you expect?

“Well, I just thought that since girls didn’t have a beard, they wouldn’t have hair any place else either.”

I began to realize just how innocent and inexperienced he really was. He quickly recovered from his discovery, and continued his exploration. Shortly, I felt his probing fingers reach the upper most part of my vaginal opening.

Be really careful, you’re inside me, I whispered.

He was careful, gently probing his fingers into my dripping opening. Since he was coming from above, and my slacks and panties considerably restricted his arm, he couldn’t get a very direct approach to me. His fingers just penetrated the opening and only slightly into me. Even so, the feeling was unlike anything I ever experienced. I ground my bottom into the divan, trying to adjust his fingers to where they felt the best. He obviously didn’t know what to do, so he just ran his fingers up and down my slit. The feeling was so intense that I finally had to stop him for fear that I would want to just keep going and g-o-i-n-g! I could tell that it was with the utmost reluctance that he pulled his hands out of my panties.

We reluctantly agreed that it was time to go to bed. My room was on the second floor, next to Dean’s room. He came into my bedroom, and held me in his arms for a long time. This would be the last time we would kiss good night for at least three months. I could see the unasked question on his face. Right at that moment, if he had asked to sleep with me, I’m not sure what the answer might have been. After several minutes, he quietly went out and softly closed the door.

The next morning I got up and quietly opened my door. Dean’s door was open to allow a breeze to circulate through the bedrooms. I peeked in to see him dressed and making the bed. I stepped into the room, wearing my pajamas. In an instant he embraced me, and without hesitation, slid his hands under my pajama tops and up my back. For several minutes, he ran his hands over my back. He paid special attention to the place where my bra would hook if I were wearing one.

Unless you want to go a whole lot further, you better go get dressed. I kissed him and heeded his advice.

The next two months were filled with daily letters back and forth. In those days, we never considered a telephone call due to the expense relative to our meager incomes. Dean worked six days a week, ten to twelve hours, and I worked a second shift job doing computer key punch work. One weekend, my sister and her family were visiting from Texas. I was helping with dinner preparations one Saturday night around July 4. I heard a car drive in, but since we were expecting the entire family I didn’t pay any attention. One of my sisters said there was someone at the door for me. I couldn’t imagine who could be at the door, but went anyway. There was Dean! He hadn’t told me he was coming, just decided on the spur of the moment to drive down for the weekend.