The First Time

Losing It

The following story is a figment of my imagination. It has a fairly slow build-up. It is not a jerking story. It just takes me back to my youth and the way things were.

Everyone was 18 or over

No animals were hurt in the writing of this story.

When I was 18 about 57 years ago, I was dating a girl (Sherry) that was also 18. We had been going together for a couple of years. Once we were both 18, we started to experiment a little more. We were both virgins not because I wanted to be but because she did.

She was a true redhead, fairly tall and had B sized boobs. She had been a dancer and had very strong shapely legs and a nice tight ass.

I didn't think I was much. I had always been a fat kid but as I was close to graduation, I had slimmed down had a few muscles and a great tan. I was not exactly shy, but I was not great with the girls. I was not aggressive at all and tried to do all the things my mother told me.

Sherry and I saw a lot of each other. Everyday while we were in high school and then after we graduated almost every single day. Even when I had to work evenings I would go to her house after I got off my summer job and we would go out to get something to eat and then we would park and neck for an hour or so.

We went out one night and had a burger and then went to our parking place. Sherry started rubbing her chest all over me. Against my arms and even so when she turned, I had my hands on her boobs. After I had a handful of her boobs, she grabbed my hand and held it to her chest. I loved it. Man, I had a hard on that wouldn't quit. I couldn't even go in her house with her after I got her home because I knew her parents would still be up, and I didn't want them to see me with a hard-on.

The next time we went out I just couldn't wait to get my hands on her. When I touched her chest, she looked at me and said, "Is my blouse in your way, put your hands inside my blouse."

Holy Cow, I almost came in my pants. I was actually touching her bra. It was not a soft one it was lacy and yet I still could feel a hard nipple through her bra. I could feel her skin. She was moaning slightly and pushing against my hands. We kissed until I think my lips were raw. We sucked on each other's tongues so much that it was almost sore.

Both of Sherry's parents worked weekends so Saturday morning she would call me and tell me her parents were at work and to come over. I want over to her house and when I knocked on the door, she answered the door wearing slacks and a blouse that was wide open and "OMG" she didn't have a bra on. Wow, my very first bare boobs. This was an instant hard-on.

I was in hog heaven, she said, "come in my room, I am still a little tired" So we went in her room. She laid down on her bed and I laid down next to her.

My hands were all over her. I was touching my first bare boobs. I was playing with her nipples. I could actually see them. As a redhead she had pale skin anyway, so her breasts were very pale. Her nipples were a darker color, and her nipples were very hard.

Sherry opened my shirt, and I could feel her chest pressed against mine. I could feel her bullet nipples pressed against me. I was running my hands all over her. She sat up and took off her blouse and I was touching her back and belly.

Dumb me was so happy touching her boobs that I never thought about putting my hand in her pants. We were very close, and my hard cock was pressed against her, and she was grinding on me. About the time I had made up my mind to put my hand in her pants there was a knock at the door and we both jumped up and had to get dressed.

I was the first dressed as all I had to do is button my shirt. I went to the door, and it was the insurance man. About that time Sherry came walking out of her room and it was obvious that she was still getting dressed. Of course, the Insurance man clicked on what we had been doing and immediately tried to sell me insurance. By the time he left Sherry was out of the mood and I went home.

After that every time we went out the first thing we did when we got to our spot was for her to open her blouse and unhook her bra so I could play with her. After I went home, I had to immediately head for the shower so I could jerk off. As a friend told me one time. "It is my shower, it is my soap, and it is my dick. I can wash it as long and as hard as I want." It was sort of embarrassing though when my mother asked me why the front of my underwear was always so stiff in the front.

My parents were not wild about Sherry. I really don't know why. I did what I wanted to. Because I was working 5 days a week and was also going to college. I guess I was really naïve and still am for that matter.

Sherry's parents decided to go out of town one weekend. She didn't want to go, and her parents didn't want her to stay alone in the house as she didn't live in the best neighborhood so my parents told her she could use our couch.

It just so happens that this was the weekend of the big block picnic. So, Saturday night we went to the block picnic with my parents next door. We ate and walked around a little bit, but it was pretty boring as there was no one else there our age so we went back to my parent's house.

We were sitting on the couch making out some and Sherry said to me. "Dan let's play truth and dare". Like I said I was pretty naïve and have never heard of that.

She explained the game to me, so I agreed to play. We went back and forth doing the truth thing for a few minutes. I finally said DARE

Sherry looked at me and said "okay suck my nipples for two minutes"

Oh, My God. It took me about 3 seconds to open her blouse and push up her bra and get my mouth on them. I may have cheated and spent more than 2 minutes on her boobs.

When my time was up, I thought maybe I should say dare too. So, it was now her turn and she said, "Truth or Dare" Of course I said Dare

She looked at me and said "I want to touch it"

I said "Touch what"

She said "Open your pants"

Dang I was so hard, and I thought I was going to cum all over myself. She reached over and pulled down my fly and reached in and grabbed my cock through my underwear. I told her she had better be careful or she would get a handful of something she hadn't seen before.

Then she said "okay your turn" of course she never let go of my cock.

I looked at her and said "I want to touch your pussy"

She said "Okay"

She had some pants that were just pull-on. We used to call them ski pants which were something like what we could call Yoga pants now only thicker. So, I pulled the waist of the pants out and put my hand in her pants. She felt very hot and wet. I was almost beside myself I had my hand on the outside of her panties, but this is the closest I have ever been to a real live pussy. I could feel her lips through her panties. Dang This was the hottest thing I have ever done.

She said "Okay my turn"

Of course, I said "Dare"

She said "I want to see it. Take it out for me."

I told her "You have it in your hand, you take it out"

Just like that my very hard cock was in her hand. She felt it all over. She got close to it and looked at every inch of it. She continued to rub it. I don't know how I kept from cumming all over her. She reached in and was rubbing my balls. I thought to myself this had to be the greatest day in my life.

I said "Okay my turn"

She stood up and faced me and pulled her pants and panties down to her knees. Wow, my first real live pussy. I noticed two things right off the bat. First, she was a real redhead. Wow real live red pussy hair. And secondly, she was really wet. I wasn't sure what that was all about as this was way before internet and being somewhat protected, I thought maybe she had wet her pants. But the smell was overpowering. Just the smell of her turned me on.

I got to touch her naked pussy. It was so amazing. So soft, so wet, so amazing.

Well once again my bad luck struck. I heard the back door open and my parents coming home. All Sherry had to do was pull her pants up and button or two and I ran for the bathroom with my hard dick standing out straight.

When I got out of the bathroom my mom and dad were sitting in their chairs. My parents asked what we were going to do this evening. I sure knew what I wanted to do but I couldn't tell my parents.

I told my parents "How about a double date? Let's all go to the drive inn movies"

My mom and dad thought that was a good idea, they hadn't been out in a long time. I told dad he got to drive, and I would buy the tickets. So, we all got ready and off we went to the drive inn. I told Sherry we had to watch it, so we sat close in the back seat. As soon as the movie started, she grabbed my cock and I put my hand in her pants. I don't think my parents figured it out, but they were cuddling in the front seat.

We got home late, and we were all tired. So, I went to bed and Sherry went to the couch to sleep. We got up the next morning and had breakfast and Sherry said she had homework and her parents would be home later so She asked if I would take her home.

When I took Sherry home her parents were still not home. She looked at me and said "What do you want me to take off"

I may be shy, but I said "Well, everything".

She walked into her bedroom, and I went and sat in the TV room which was what would have been a dining room when the house was build. About that time her dad walked into the house. He sat in a chair with his back to the living room.

Sherry came out of her bedroom wearing a robe. She saw her dad sitting in the chair. So, she laid on the floor behind him. She opened her robe and sure enough she was totally naked. She laid there and opened her legs as far as she could.

I about shit a brick. All her dad had to do is turn around and he would have seen her totally naked. There is no way she could cover up if her dad started to move and turn around. Of course, I wanted to look, and I did so I was surprised when her dad didn't turn around.

Sherry laid there and started rubbing her pussy as I watched. I could see the moisture glistening on her pussy. After about 5 minutes she stands up and closes the robe and came into the room with her dad and I

Sherry sat next to me as close as she could possibly could. Her robe opened and it was possible to tell that she must not have had much under the robe as I could see her thighs down. I was getting very uncomfortable sitting there with her dad sitting right there. I don't want to say I was afraid of him, but I was not comfortable around him.

I got up to leave and she followed me to the door. She started kissing me good-bye and as we stood there by the door, she took my hand and put it on her bare pussy. I left, got out of the house, got in my car, and headed home.

As soon as I got home, I headed to the shower. I needed to jack off so bad. I had a major case of blue balls.

It didn't take me long to teach her how to give me a hand job. I could make her come with my fingers and she liked that, but I needed something too. Of course, by now I am begging her to let me fuck her but that was not to be.

We spent more and more time at our parking place. I always went home with fingers that I could smell all night long after I went to bed.

Sherry had an older sister and Her sister Pat, and her cousin Pam had gone to Texas to visit two guys that they met before the guys went into the Army. When Pat and Pam came back from Texas, they were both engaged. They had started planning on a double weeding on Valentine's Day. Of course, that put everyone in overdrive to get ready for the Big Wedding. Sherry was going to be a bridesmaid and I was even going to be in the wedding as a Groomsman. They got back the end of September and they said they only had four and a half months to get ready.

With Bridal Shower coming up for Pat, Sherry had me take her shopping as she wanted to find something sexy for her sister's Bridal Shower. So, we spent most of the evening in the lingerie department. Sherry found what I would best describe as a nighty that looked like a totally see-through string bikini.

When we get back to the house Sherry's mom and dad were sitting in the living room. So, I sat in the living room with them.

"Sherry says "I got this thing for Pat, and I want to show Dan how it looks when it is on"

She grabs the bag and heads for the bathroom. A couple of minutes later I her walking into the living room where her mom, dad, and I are siting. Well, I dang sure wasn't wrong. I could see everything. I could see her nipples and her Red Pussy almost like she didn't have anything on. She turned around and I could see every inch of her ass.

I figured okay this is where her dad kills me. Strangely enough neither parent said a word. It was like they didn't really care if Sherry walked around in front of me naked. Sherry walked around a couple of minutes with this see-through thing on and then went back to change into her regular clothes.

When we had been shopping Sherry had on a Skirt and blouse. During that time girls wore girdles to hold up their nylons. She came out of the bathroom wearing that skirt and blouse. I was sitting in an armchair and Sherry came over and sat on the Arm of the chair with her feet in the chair facing me. As I looked over and she opened her legs, and I could see she didn't have any panties on. I was sitting there starring at her crotch.

After sitting there for about 5 minutes with me looking at her pussy the entire time Sherry said, "Let's go get a burger". She put on her shoes, and we headed out the door.

We went to a drive-in restaurant and got a burger. As we were sitting there in the car Sherry pulled her skirt up to her waist. Needless to say, I just didn't sit there. I had my hands all over her.

I guess it was about this time I realized that Sherry was a major exhibitionist. I had heard of that before and now I realized she was the definition of exhibitionist.

As a bit of a side, when Christmas arrived, I was invited to Sherry's brother's house for a Christmas Party. Sherry's brother Dennis was in the National Guard and was still in training. So, the party was put on by his wife. The house had a basement and that is where the party was. So, we were all in the basement eating, drinking, and talking. Sherry's Sister-in-Law Denise came to me and asked me to come upstairs with her and help her with something. When we went upstairs, Denise had me stand in a doorway and then she kissed me.

I said "What the heck"

"Look up"

I looked up and saw that there was mistletoe hanging in the doorway. She kissed me again and I could see her tongue entering my mouth.

Denise was shorter than Sherry, she was also a redhead. She was much more petite than Sherry with probably a 32B chest. Actually, she was very good looking.

Denise said "Meet me up here in about 30 minutes"

Well, I did go upstairs 30 minutes later, and Denise was nowhere to be seen. I went to the bathroom, and I heard her in the bedroom. I called out her name and she said to come in she needed me to help her. So, I go in the bedroom and ask her how I can help.

She said, "never mind I did it."

I asked what and she said, "I wanted you to help me change a light bulb" She pointed at a bedside lamp which was turned on.

"I forgot that I already changed it. Have a seat in that chair"

I sat in the chair, and she came over and sat in my lap. She placed her lips on mine and I felt her tongue brush my lips. I opened my lips, and her tongue invaded my mouth. We sat there and kept kissing. She, I am sure, could feel my hardness pushing up at her. She took my hand and placed it on her breast. They were smaller but they felt really good. We spent about 15 minutes "making out" until I heard Sherry calling my name. I have to admit this made me horny as hell. The fact that Denise's husband was in the military and what I done was weighing heavily on my conscious.

I left the room and went back downstairs where Sherry was. She asked me where I had been, and I told her that I had been helping her sister-in-law changing some lightbulbs.

I told Sherry it was time to go.

We left shortly after that, and I started taking Sherry home. I have to admit that that we did not go directly home. We had to go to our place and play for a while.

I would pick up Sherry from work and I would take her home. The first thing she would do is take off her clothes. We were in Sherry's bedroom, and she was naked. I actually was still dressed. The phone rang and she jumped up and went to the telephone (there were no cell phones then). I walked into the room the telephone was in and started laughing. Sherry was standing there totally naked holding one of her mother's dresses in front of her. I guess she didn't want the person on the phone to know she was naked. I just kept laughing and the girlfriend she was talking to asked why I was laughing so hard. And believe it or not Sherry tells her why I am laughing. She tells her friend that she was naked holding a dress in front of her so her friend wouldn't know.

"DUH" The bad part is the friend was a friend of hers from Church. You have to remember that 57 years ago women were all supposed to save themselves for marriage and not have any nasty thoughts. Evidently, she told Sherry's mother about the incident but not a thing was said to me. Sherry's mother just told her not to get pregnant.

As time moved on and still not being allowed to have sex with Sherry. We decided to go to a huge amusement park that had a beach that was close by. So, we took our bathing suits. We spent the morning riding rides and having fun and decided to go to the beach after we ate lunch.

We both had our bathing suits on under our clothes, so we went to the beach and started swimming. We played in the water and had a ball. Sherry swam off and I heard her call my name. I looked over and she was floating on her back totally naked. It is amazing how bright that red pubic hair almost glows in the sunlight. It would have been okay but there were many people swimming at the beach on this hot day. I walked over and pushed her under water. I am positive now that she is an exhibitionist. I told her it was time to get out of the water and go ride rides again. We walked back out to the parking lot to get dressed in my car.

When we got back to the car Sherry stripped off and sat in the back seat of my car totally naked. I barely had time to put the top up on my convertible before she got naked. She put her dry shorts on and a bikini top. I put on shorts and shirt. We decided it was getting late so we would head back to her house. The amusement park was about a 45-minute drive from home. I put the top down on the car to enjoy the weather. After we left the parking lot Sherry removed the bikini top. I reminded her that people driving next to us could see her titties. She told me she didn't care. She leaned over opened my pants and licked and played with my cock the entire 45 minutes' drive home. The truckers seem to get a big kick out of seeing her topless as every time we passed one or they passed us there were lots of horns honking.

Upon arriving at her house, we found no one was at home. Her parents were still at work. She had me lay on the couch and she started licking my cock again. After 45 minutes of her teasing, I couldn't hold back any longer and I came in her mouth. My very first blow job.

I guess she forgot when I came stuff came out of my rod. She got this strange look on her face and threw up on me. OMG covered with half digested carnival food. Yucky. I never asked her to do that again. Many years later I found this was one of my favorite things.

Sherry's parents had a lake cabin about an hour away. We convinced her parents to let us have a weekend at the cabin. We left Friday after work and drove up to the cabin. Not far from the cabin was a dance hall so after we arrived, we cleaned up and then headed for the dance hall. We danced and had fun until they closed. We headed back go the cabin. When we arrived, we decided to go swimming? Of course, we were going to skinny dip. We swam around for a while to cool off from all the dancing. We got out of the water and noticed that there were no neighbors who were up that weekend, so we walked back to the cabin hand in hand naked.