No Regrets?

I saw mum standing in the lounge, looking through the triple glazed windows into the grounds beyond. Our lounge is on the second floor of the house and the views are spectacular. 

Don’t ask me what it was, but there was something about the way she was standing that was so terribly sad. In fact, sadness seemed to be pouring off her. As I approached her I could see silent tears rolling down her cheek. Wherever she was in her head, it wasn’t in the here and now. 

When she realised I was there, she flinched and hastily wiped the tears away, but she knew the damage was done. I had seen what I had seen and there was no undoing it. “Give me five minutes, then come to my den.” Invites to dad’s den are rare. Invites to mum’s den are as rare as finding a freshly laid dodo egg on the lawn! 

Mums den is a haven of softness, tranquility, incense and the best hot chocolate on the surface of the planet. Mum indicated I should sit down and handed me a cup of warm liquid heaven. Then she began to speak…

“…I was 15. I suppose like most 15 year olds, I hadn’t quite worked everything out yet, and neither had Charlotte, my best friend. We would talk for hours about boys and what we wanted to do….or rather, what we thought we wanted to do….we didn’t know for sure of course. Then one night Charlotte snuggled in bed with me. It felt strange but also nice. We didn’t do anything…just went to sleep in each other’s arms. 

When I woke up the next morning, Charlotte’s hand was under my t shirt holding my boob and gently rubbing my nipple. It made me feel funny between my legs, but funny in a nice way. I felt her moving next to me and that was because her left hand was jammed between her legs. I just lay there, frozen as she touched me, and when her hand moved south, I didn’t try to stop her. She touched my vagina and found my clitoris so easily. I felt myself close to an orgasm, but tried to fight it off. Then, I felt Charlotte cum, and I came with her. 

For about eight months, until we were well into our 16th year, we would fool around together. Then, we’ll, she got a boyfriend, I got a boyfriend and it jut stopped. Sometimes, I think back to those years. I wonder if Charlotte remembers me and what we did. Sometimes I wonder where she is. I hope she is having a happy life and doesn’t regret our teenage experimenting. I know I don’t. 

I also know I’m not bi-sexual. I’m definitely fully heterosexual. What we did was just….what it was…experimenting…finding out…I don’t regret it for a moment. I just sometimes look back on it fondly.”

By the time she had finished I had a tear rolling down my face too. I wonder….how many women sometimes look back on that brief experiment they had, It may have been just one time, at a sleepover when things got goofy. Or it may have been a glorious summer of fun and experimenting. 

I know for a fact that several of my closest friends had g/g experiences. I know one girl, let’s call her Amanda, who had an experience with her best friend. It was once only. One night. Amanda told me that it went from a cuddle because she was upset to kissing to touching to…well..pretty much everything two girls can do in the course of one night. In the morning Amanda felt amazing, but her friend had got up, dressed and gone before she woke up. They never spoke again. Amanda deeply regrets losing that friendship and has tried on numerous occasions to build bridges. 

Tilly and Maisie were two more friends who I know fooled around. Like many, when Uni came around, they went their separate ways and eventually lost touch. 

And me? Do I have regrets? Missed opportunities? 

Yes. Yes I do. The second boy to get into my panties. Steve was far from a hunk, and certainly wasn’t captain of the school rugby team. He was on the thin, almost weedy side, but was a beautiful soul…an old soul, I think. Kind, attentive, and unlike most boys his age wasn’t hell bent on getting into my panties. 

Slowly, I began to remember the day he did get into them. It was an afternoon and there had been some kind of emergency and the school had closed at midday. Steve had walked me home in his typical chivalrous style, and in return, I’d invited him in. We had the house to ourselves, and even when we got to my bedroom, he still didn’t make a move. In fact I was beginning to feel cross that he hadn’t. 

Then he asked is he could say something. (Say? I wanted him to throw me on the bed and fuck my brains out…and he wanted to talk??? Grrr!) Naturally, I said he could. I remember he took a deep breath and said “This will probably come out wrong, but….well, one day, someone is going to get into your panties. I just hope, whoever he is, that he realises what a privilege that is going to be.”. 

I walked over to him, pulled him up out of his chair and hugged him, telling him that’s the sweetest thing anyone had ever said to me. Then I took his right hand and put it up my skirt. “It could be you if you like.”

He did like. Oh, he liked very much. He undressed me slowly, taking care over each button, each zipper. When he got to my underwear, he didn’t miss a beat. There was no inept tugging or pulling. He undid my bra and slipped my panties down. Then I slowly undressed him. Well, he might have been weedy, but his cock wasnt! He kissed me onto my bed and actually asked if I wanted to go all the way. (I’m not sure how he could have missed the signals. Anna on he back, legs spread wide and soaking wet is a bit of a come on in anyones book.)

He fucked me slowly, almost too gently, but the length and girth of his cock more than compensated. Come the moment, the sweetheart actually asked if he could cum in me. I wasn’t on the pill, but I still told him he could. It was beautiful. (Oh don’t worry, I was due on the next morning.)

Even back then, I knew my leanings were more to girls and I knew, deep down that Steve and I wouldn’t be long term. In fact we had three months of beautiful sex and even more beautiful relationship. I still think Steve was an ‘old soul’. He brought be flowers, chocolates and, bless him, there’s no other word for it…he courted me exquisitely. This was no 18 year old jock trying to fuck anything in a skirt. 

We reached a point where we both realised it wasn’t going any further. I agonised for a week or more over how I would tell him. In the end, he even spared me that. He told me that he didn’t feel worthy of me, and that he felt he would only disappoint me in the end, blah blah blah, and that he felt he should let me go. There were tears on both sides. His, I think we’re genuine regret. Mine, I have to be honest, we’re partly relief. I mean, what was I going to say? “Steve, your perfect…every girls dream….and you fuck me to the stars and back….but frankly, I prefer another girl’s cunt.” No….I wouldn’t have said that. But it would have been true. 

So, Steve slid out of my world. I don’t know where he is now, but when I stand looking wistfully out of my windows, I sometimes think of Steve. I hope he found a girl who deserves someone as kind and thoughtful as he is.

As I thought about what mum had said, and my memories of Steve, I felt something strange. Something new….different. Oh I was wet, of course, thinking about Steve always makes me wet, but he horny feeling that came with it was different. Running parallel with it were thoughts of other people who, in their pasts had that special encounter, be it one night or longer. One moment when they threw caution and convention to the wind and just went with it…went with something beautiful. It could be the priest in the seminary finally jacking off and deciding no, this isn’t sinful. Or those two 14 year old girls exploring each other’s developing bodies together. Or maybe it’s Mr Michaels in the property next to ours. Maybe he, in his outrageously expensive private school had an a counter behind he cricket nets one summer. 

Slowly, my hand reached into my panties and my finger began circling my clit. The arousal grew sharply, as I knew it would, but also, something else. This orgasm would be for everyone who had that unrepeatable experience….that moment….whether they regret it, or look back on it with longing. If you can pray for others, why can’t I cum for others? 

My finger circled my clit. It was a million girls’ tongues, on a million girls’ clits. It was a million boys with a million boys. And it was Steve, licking my little bean to perfection. 

The orgasm was immense…..it seemed to radiate from me like a shockwave from an explosion. 

I like to think it travelled into the world and that anywhere there are others looking wistfully into the past, perhaps it made them smile.