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My First Time

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Ann and I met when we were freshmen in high school. She was dating a friend of mine, and we used to double date, frequently going to the drive-in, etc. When my friend left town the summer between our freshman and sophomore years, Ann and I started dating. We were both pretty inexperienced sexually, Ann probably more so than me. I had done some heavy petting during my 9th grade year, and had actually gotten my hand in a girl named Jean’s panties. We didn’t do much, but I had penetrated her vagina with a couple of fingers.

Ann and my friend had kissed on occasion, but no petting at all. Ann’s parents were very realistic about their daughter and her dating, and rather than have her parking in cars with her boyfriends, they provided a “sitting room” - which was actually sort of a den - off of their living room where she and her beau’s could spend time together. This room had three doors, one off of the entry way, one from the dining room, and one from the kitchen. The rules were that the door from the kitchen must always be left open.

When Ann and I started dating, we always went back to her house and eventually ended up in the “sitting room”. My intentions towards Ann were completely different than with other girls I had dated, and I had to much respect for her to try and do what I done with Jean. As our relationship progressed however, we became more and more familiar with each other, and we began to experiment a little. This led to our initial stages of petting, with me touching Ann’s breasts through her blouse, then eventually getting my hand inside her bra.

We dated all through our sophomore year and the summer before our junior year we became even more experimental. Ann’s parents had a pontoon boat at one of the local lakes, and the four of us spent almost every week-end cruising the lake. During this time I became like one of the family. Because we spent so much time in bathing suits, there were amble opportunities for to lower Ann’s top and for me to kiss and massage her petite breasts and excitable nipples. On more than one occasion my hand moved lower and found itself inside the lower part of her suit massaging her virgin genitals.

During the school year that followed, I started going to Ann’s house and having lunch with her mother, May. Ann and I had different lunch hours and her house was fairly close to school so it was convenient and fun for me.

May was a very attractive woman, and during the preceding summer I had found myself looking at her in her bathing suit more than once. She and I seemed to hit it off from the very beginning and both she and I; and, she and I and Ann, had had a few conversations about sex. Each time I had found myself thinking not only about what Ann and I were learning together, but what sex with May might be like.

As the year progressed, the conversations May and I had at lunch together seemed to be more and more about sex. One day I mentioned to May that I had a spot on my penis that I was concerned with and didn’t know what I should do.

May suggested that I see my family doctor. I told her that that was what I thought I should do, but felt comfortable enough with her that I wondered if she would mind looking at it first. May volunteered that she certainly wasn’t much of an expert, but if I really wanted her to she would be happy to look at it and see if she thought there was need for concern.

I told her that I really would appreciate it, so we proceeded to the “sitting room” where I sat on the couch and pondered what to do next. I think May could tell that I was nervous and unsure as to how to proceed, so she suggested that I just lean back against the back of the couch, and unzip, then lower my pants and shorts. As I lay back, I had a raging hard on and when I slid my clothes down, my penis sprang free and was probably was as hard as it had ever been before.


May sat on the edge of the couch next to me then, and said, “Ok, what is it that you’re concerned about?”

I was obviously somewhat embarrassed, in large part because of the huge erection I had, but also because this was really the first non family female I had even been naked in front of – or exposed if not naked. I did have a spot on my penis, a mole or something in actuality, and so I pointed to that and said, “this spot right here”.

When May reached over and touched the spot, I must have jumped a foot off the couch. “Oh God May,” I said. “I don’t know why I have a hard on (I didn’t really know to use the word erection), I’m really sorry.”

“No need to be Ted,” she said. “Just a natural reaction I think. This just looks like a mole or freckle to me. Is it new?”

“Yes,” I answered. “I just noticed it a few days ago.”

“Well, I think it’s harmless enough. Just keep an eye on it and if it changes any go see your doctor.”

“Ok,” I managed to squeak out.

During all this conversation, May had actually taken my penis in her hand to make her examination. My penis was rock hard now, and in the position I was sitting, it was curved upward and almost laying flat against my stomach. It was even bigger by now - if that was possible - and I think some pre-come had even began to seep out of the end. I finally got up enough nerve to talk again.

“May,” I began, “I don’t how to say this, and it is embarrassing, but is it normal for me to get hard like this?”

May laughed when she answered and said, “Yes Ted, quite normal, and you don’t need to be embarrassed.”

“It just feels funny for you to see me like this.”

“Well, your reaction is very normal. Actually, touching your penis and seeing you like this has caused a reaction in me too - without any conscious effort on my part - if that makes you feel better.”

“Really! What kind of a reaction?”

May laughed a little nervously at that, “How do I explain this? I know you and Ann have been kissing pretty heavily, and that is to be expected after the length of time you have been dating; but, have you ever touched her between her legs?”

I think she could tell by the expression on my face that I was horrified by her question.

“Don’t be afraid to tell me, its okay.”

“Only a couple of times.” I answered hesitantly, but honestly.

“Was she wet?”


”Well, that is because when a woman becomes excited, or maybe aroused is a better word, her vagina and genitals become lubricated. Intercourse would be impossible without a lot of lubrication. A dry penis and vagina don’t go together very well.”

“Oh,” I managed to get out. “I guess I never thought about it. Is that the kind of reaction you were talking about?”

“Yes,” May answered. “I can tell that I am somewhat wet from our conversation - and seeing you like you are.”

May paused for a few moments, as if pondering something, then asked, “Have you ever seen a women naked before, Ted?”

“My mother and sister a couple of times is all.” I answered. “But only at a distance.”

“Than you haven’t really seen them up close.”

“No, not at all.”

“Do you want to see me without my clothes on?”

Before I could answer she continued. “I wouldn’t mind, and feel comfortable enough with you for you to look at me if you want. Only in an educational way of course.”

“Really May!” I exclaimed. “I have to tell you that I have dreamt about that - many times.”

“Really! That’s very flattering.” she proceeded.

May stood up then, and was standing in front of me as I watched in fascination as she unbuttoned her blouse, then slowly took it off. Just seeing her there in her bra and slacks was making my penis twitch and I had to use all of the will power I could muster to keep from touching myself. May was looking back at me, mostly my huge hard on as she unzipped her slacks and slowly slid then down over her hips, and then off her legs. I was really in awe now, seeing a grown woman stand there in her bra and panties had me in a state of excitement like I had never experienced before.

Still looking at me, she reached around and unhooked her bra, then took it off, exposing her lovely breasts. May was not big in the breast department; however, I thought they were lovely and couldn’t take my eyes off her - by now - very hard nipples. I noticed how much darker they appeared than her daughter Ann’s.

As she stood there in only her panties, she looked at me for a brief moment, then without hesitation, hooked her thumbs inside the elastic and slowly slid them down. When her pubic hair came into sight, I think I actually let out an actual gasp. May’s pubic hair must have been trimmed a little, for even though it was quite dark, as soon as her panties were down to mid thigh, I could see her pubic lips and my imagination told me more inside those. I was in never, never land. I don’t know if my mouth had dropped open or not, but I couldn’t keep myself from just staring at her pubis.

“Now it’s my turn to be embarrassed,” May said, “your staring at me like that makes me feel funny and a little uncomfortable too. I don’t know what to do next,” she sort of laughed out. “Why don’t you move over and let me sit there.”

May sat down next to me then, and leaned back into the corner of the couch. “I don’t know what the best way to do this is, but I guess I need to spread my legs if you are to make a proper examination.”

May leaned against the back of the couch and pulled her legs up so that her heels were just resting on the edge of the cushions. This was probably as close as she could get to being in the stirrups at a doctors office without actually being there. Her legs were spread as wide as she could get them and her vulva was now completely open for my inspection. My eyes were immediately drawn to the pinkness between her legs as she moved her hands down to touch herself and expose her inner most self to me.

She took both hands, and spread her lips, touching herself at the very top of her pubic lips. She pulled the sheath back hiding her clitoris and then as the little head appeared, she touched it saying, “This is my clitoris Ted, which is sort of like the equivalent to your penis. It gets hard just like you, and is very sensitive.” As she rubbed it with her finger, I could see that it was growing hard actually starting to get bigger. “You can touch it if you want.”

I slowly took my hand and started to move it towards her, and sensing my hesitation, May took it and proceeded to place my finger against her clitoris. “See how hard it is, and you can tell now how wet I am. This is my vagina.” As she placed my finger at the entrance. As wet as she was, the tip of my finger just slid inside. I was mesmerized as I watched and felt my finger disappear inside her dripping hole.

“Oh Ted, I don’t know how to say this, but you are making me even more aroused, and feeling quite good.”

“I feel really funny May. I am twitching down here [as I glanced down towards my raging hard-on], and I feel really different.”

“Have you ever masturbated Ted?”

“Ah - A”

“Don’t be embarrassed - I’m sure you have. I think all boys do.”

“Well - yes.” I answered embarrassingly.

“Do you sort of feel right now sort of like you do just before when you make yourself come?”

“I guess that’s it.”

“Well why don’t you take your clothes off the rest of the way, and if you do ejaculate don’t worry about it. We just don’t want to get it all over your clothes.”

“OK,” I said as I stood up and slid my pants and shorts off the rest of the way, then removed my shirt. As I stood there, my penis was sticking straight out and up, and there was no doubt now that a considerable amount of clear liquid had escaped from my urethra.

“Why don’t you sit back down,” May said - as she patted the spot between her spread legs.

I sat down right next to her exposed pussy then, and sort of leaned back against her right leg which was still cocked up against the back of the couch. May surprised me then as she reached down and touched the tip of my penis.

“You are obviously as aroused as I am, Ted. This liquid is lubrication to enable you to have intercourse.

“Did you know that?”

“I guess so,” I sort of stammered in response.

“Isn’t it amazing how a man and woman are built for each other. My vagina and your penis are just made for each other.”

“May. I know that it probably will, but it doesn’t look like your vagina is big enough for my dick - whoops, I’m sorry - my penis, to fit into.

May laughed out loud then. “Oh it will fit Ted. Do you want to just touch the tip of it, or put just the head into me?”

“Oh yes May! Are you sure you want me to?”

“Yes darling! I want you to. I would love to be the first woman for you to enter. Go ahead, touch me with your penis.”

I moved around then so that I was between May’s legs and she took my penis and placed it at the opening of her vagina. I could feel her wetness then, and a warmth like I had never felt before. As she pushed against me, and me against her, the tip, then head of my huge erection slid easily inside her hot and dripping canal.

The heat around my penis was almost overwhelming, and even though I had been masturbating regularly for several years, the sensation was unbelievable. May spread her legs wider then, and I felt her legs wrap around me and pull me deeper and farther inside her. She was so wet and hot, that with a couple of in and out movements, I slid easily all the way in. Instinct took over at this point I guess, and I pulled almost all the way back out, then began the natural movements of an experienced lover. The excitement and preceding events were too much for me however, and after only a couple of thrusts I exploded with my first coital orgasm, and shot my first load of come deep inside May’s receptive body.

May must have been expecting this, because she just held me close and kissed me all over my face and just massaged my back and down over my hips and buttocks. I just lay there and sort of collapsed, but my penis stayed fairly hard and remained inside her sopping vagina.

“Oh God May,” was all I could say. “I’ve never felt anything like that before. I’m sorry. I’m supposed to make you feel good to.”

“Don’t worry darling, you did make me feel good, and we have lots of time for that.”

May’s legs were way up around my hips now, and her heels were resting just below my buttocks holding me with all her might. I looked down at her then, and we kissed for the first time. Her mouth opened wide and my tongue moved in to began it’s passionate dance with hers. This caused an almost immediate reaction in me, and I felt my penis get hard again and push back deep inside my lovers hot canal. I began moving faster, deeper and longer now, and before long felt that now familiar building towards that wonderful relief. This time however, May was with me, and after a few minutes we reached a wonderful mutual orgasm. I felt for the first time, that wonderful feeling of not only being satisfied, but the equal - or even greater satisfaction - of satisfying another. May went wild underneath me, and I felt her vaginal contractions sucking me dry as her legs and arms pulled with all their might. We continued like that for what seemed like forever until we collapsed together and then just held each other in a lovers embrace for many minutes afterwards.

May and I talked about what we had done afterwards, and I think we both knew that we crossed a forbidden barrier. I think we also both knew that we would never talk about it again, or that it would ever happen again - which it didn’t.

I continued to date Ann, and to spend a lot of time with the family. Obviously, May and I had a special relationship, and later during that same year, Ann and I experienced together what May and I had earlier. It was the first time for Ann, and I’m sure I was able to make it better for her because of that wonderful afternoon I had had with her mother. I don’t know if that was May’s objective, or whether she just got carried away that afternoon, and the benefit Ann received was coincidental - nor do I really care. As far as I’m concerned - we all benefited - and I have wonderful memories of my only mother and daughter lovers.

Ann and I both married other people, and have very successful marriages. May and I still communicate, and even though our afternoon goes unmentioned, I’m sure it adds to the special relationship I know we still share.

submitted by Ted of tednbarbmn

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