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My Sister's Boyfriend Had a Couple of M/M Experiences!

Posted by: Age: 22 Posted on: 2 comments
6 likes 15 views Category: Masturbation Female Solo Tags: Sexual emergence, exploration,

This is down as female masturbation thanks only to Miss Brain, who painted photo-realistic images for me…and kept them coming. I will write it as he said it. I have an eidetic memory for what people say to me, so this will be almost 100% accurate. 

Oh, it’s also going to sound more m/m. But wait until the end….(yeah, about that…it’s also quite long.) 


As you know, there’s an arrangement whereby I fuck Alison’s boyfriend while she’s in hospital…it gives me the cock I need, and it relieves his frustrations. But it’s not all mind blowing fucking…well…it is, but we also talk sometimes.

It turns out Chris has had a couple of boy/boy experiences in his early teenage years. 

“There was this boy called Allan. Actually, hold that thought. Us boys had a rough game we called ‘Bennying’. I don’t know why it was called that. Anyway, it worked like this. One boy would grab another from behind, and pull his arms back so he couldn’t resist. Then at the same time he’d yell “Benny!” The other boys would attack the boy being held by darting in and poking at his dick. It made the boy being held jump. I guess it was popular because if you were the one doing the holding, you had this nice soft bum against your dick that was pressing backwards and moving all the time. 

Sometimes, the boy being held got a hard on too which always provoked much jeering and accusations of “Fairy!” It wasn’t meant nastily because we knew any one of us might be in that position next time. 

So…Allan. He had quite feminine features, and it wouldn’t surprise me at all if he turned out to be gay. I lost track of him when he went to Uni. Anyway…this one day….I’d grabbed Allan and yelled “benny” as usual, and the guys all dived in on the attack. I felt Allan’s bum twitching and pressing against me, and I have to admit it felt pretty good…but then at 13, anything feels pretty good, you know? On this one occasion someone yelled “Teacher” and the group scattered. In fact there wasn’t a teacher in sight. This was just another addition to the game. Allan slumped against me and I asked him if he was ok. He said he was…and then said, ‘It’s nice here. I can feel your cock against me…..we should try this naked one day.’ Now, remember, boys like us were always daring one another to do dirty things. There was a lot of boasting….who had wanked….who had ejaculated….who had kissed a girl…who had felt a girl….that kind of thing, but as he lay against me, it just felt….nice…so I said yeah…I don’t mind. Any time. That afternoon he caught up with me walking home from school and said ‘How about now?’ He led me off the road and into the woods. (Me…there’s so much woodland and farmland around here…I bet it’s seen more sexual activity over the years than many porn films) 

We got deep into the woods…and I mean deep. Well away from the footpaths. I guess Allan had been here before. As soon as we got to his chosen spot, a nice little clearing, grassy, mossy floor and sunlight…I remember how the sunlight lanced through the trees…it was so warm a comfortable. Allan immediately undressed and then said ‘well..go on then. I was more hesitant but I stripped naked too. I’d been naked outdoors before and it always gave me an erection - even when I was just on my own - Allan turned his back and settled against me. I was hard and my cock was pressed against my tummy by his bum cheeks, in fact, the crack of his bum caressed my cock wonderfully. He leaned his head back on my shoulder. Then he took my right hand, brought it round himself and told me to ‘benny’ him. I tried to, but what I found was his erection. So I took hold of it and wanked him. He began breathing really deeply and telling me not to stop. Then he said, ‘I’m gonna shoot’. 

We all said we could ejaculate, but I don’t think we all could. Allan could though! Wow…yeah…Allan could. I saw it arc away from him and land on the grass and moss. When he’d finished, he moved slightly and said, ‘Hmm…someone’s ready. Do you want me to do you, or are you happy there?’ I didn’t know what he meant, so I said I was happy here. He began rhythmically pushing back against me and clenching his bum against my cock. I remember feeling this…oh wow….sensation. I wanted to feel him again, so I cupped his balls with one hand and held his wet cock with the other. And I came. Just like that. There was no question of me fucking him anally or anything like that…we were way to young and inexperienced…but this….well…this was something else.” 

Chris went on to open his heart to me. 

We both had to clean up. Although I hadn’t cum as much as Allan, we were both wet, and typical of us, neither of us had thought through getting semen on each other. Thank God for Doc leaves! Anyway, as we walked back, I asked Allan if he had ever done anything else with another boy. He was quite dreamy when he said, no, but there’s things I’d like to try. I asked him what. I don’t know what I was expecting…it certainly wasn’t what you see on male/male porn, but he said, ‘I’d like to go to bed with a boy and just kiss….you know? Be naked…and kiss. Maybe we could try humping as well. And I’d really like to kiss a boy down there. I know girls do it…but…well…yeah, I’d like to be in bed with a boy.’. 

I don’t know why I said it, or even if I meant it, but I said, ‘I’ll do it.’ Anyway, we all just carried on as we were, just being a bunch of adolescent boys, until one Saturday, Allan called and said his parents were out for the day. Even though this was weeks later, I instantly remembered, and equally instantly felt a tingle all over. I biked round to his house and we went upstairs to his room. Once there, we turned out backs on each other and got undressed. I don’t know why we didn’t look, but we didn’t. It was really warm in his room…it was South facing and…well…it was warm. Allan had put a large beach towel on his bed ‘in case’ as he put it. Then we just got on the bed and lay side by side for a while before moving closer and hugging. Then he kissed me. Gently and with no urgency. I kissed him back. Oh we were hard..of course we were. At 13, anything makes a boy hard! So, we kissed, and somehow I was on top of him…I don’t remember how that happened. I do remember his legs were spread wide and my dick was again between his bum cheeks while his was pressed up and flat against him between us. I tried a few pushes, but the towel was kind rough and scratchy on me. Allan asked if he could try and so we swapped. He liked it, but also said it was too scratchy. I don’t know…if it had just been the sheet, then maybe…

Either way, we went back to kissing, but I was on my back. Allan kissed my chest which I found strangely exciting. (Me. I’ve found a lot of guys like their nipples sucked and nibbled) and as he got closer to my cock I felt shivery. Then I felt his take me in his mouth…I felt his lips, his tongue and him sucking. It was way too much for me and I felt myself cum. I knew I had ‘shot’ as we called it, and that it must have gone in his mouth. What I didn’t know is that he had swallowed it all. When it was my turn, I found that I didn’t like the taste at all….too slimy…too salty…but fairs fair…I kept it up for as long as I could, then Allan, who, looking back, must have sensed my dislike, said, “benny me”, so we stood up, he backed against me and I wrapped my arms around him, grabbing his cock as I did so. This time, I remembered what having my nipple kissed felt like, so instead of cupping his balls, I tickled his nipple with one hand and wanked him with the other. Oh, and I kissed his neck. That made him cum onto the towel. 

We spent the afternoon fooling around like that. 

I got a girlfriend soon after, but I remember what Allan and I did. Sometimes, even now, well, it’s a good memory. 

That night, with Emily away on business, and Elizabeth either sleeping peacefully or masturbating a few rooms away, Miss Brain got her paint box out and gave me some pictures of two young, innocent boys exploring each other for the first time. She also gave me a commentary and reminded me that adolescent boys compare cock sizes, play masturbation games, and, like Chris and Allan, sometimes explore more intimately and together. 

What made me cum as I gently masturbated in my panties, was the thought of Chris and Allan kissing, and Chris in that forest, cupping Allan’s balls with one hand while jacking him off with the other…and his cock pressing against Allan’s bum cheeks. 

Lying there, post cum, it made me think back to all those innocent girly hugs…or were they so innocent? Tiny, budding boobs, pressed together….the race to persuade our mums to allow us our first bikinis. The sleepovers where padding around naked was a ‘thing’, but looking back, being naked was itself a ‘thing’, let alone in the presence of other girls. I know for a fact that I wasn’t the only girl to get turned in, just by sitting naked with others. It felt so ‘grown up’ to be, or at least pretend to be, comfortable with nudity with each other…oh, and we would hug naked too. 

Miss Brain notices and records things and sometimes brings them to the fore…like that Halloween, where we sat naked cross-legged in a circle in my room, flashlight held under our chins for effect, while we told scary - and sometimes scary and sexy- stories to each other. I noticed two girls link arms, and them their arms round each other’s waists. And Miss Brain reminded me how they responded to the sexy stories. I had forgotten I’d noticed them getting wet. I had also forgotten that when a sexy story finished there would be some general goofing around from all of us, but these two always, somehow, ended up kissing a little…they also shared a double sleeping bag. 

Miss Brain painted a quite delightful image of them quietly fingering each other during the night…and I came in my panties for the second time. 

And Elizabeth. Pure, virginal Elizabeth. Unquestionably when her periods started, she, like everyone, would have begun to experience sexual feelings….the firm almost aching tits, the throbbing clit, the wetness. When did that happen for her? If I had to guess, I would say around 12 or 13. By 15, she must have been a hot mess down below sometimes. No boyfriend - ever - so what then? Fingers? A nice buzzing game controller? A mobile phone set to silent? I’ve seen one pair of her panties, so I am certain without doubt that she knows what an orgasm is. 

And as my mind wandered across the hallway and one room down, passed invisibly through the oak door and saw her lying on her bed, legs flat but spread, head turned to one side as if to distance herself from what her right hand was doing in her panties…the number of times she tried to stop herself, only to start again…how she bit on the knuckle of her left thumb as the intensity between her legs rose, plateaued, rose, plateaued, and rose again, before she came into her undies in a series of high-pitched little gasps, trying so desperately to keep silent….while I came noisily into my panties for the third time.

Exploration - it happens when it’s time for it to happen. It happens subtly, sometimes even subliminally, sometimes more overtly, but it happens. Whether it be self-exploration, or exploration with another, it is, I feel, inevitable. 

Thoughts, images, feelings, all hormone-created, but all socially conditioned. From a home environment where the adolescent child finds themselves looked on a a thing of sin, instructed, dirty, to a home where sexual emergence is celebrated, there is a wide spectrum. I know a girl whose mum bought her a vibrator, wrapped it in a box with a ribbon and left it on her bed. 

My own parents presented me and Ali with a single red rose when we had our first period. 

Equally, I know a girl who was lectured (while on her knees) about the ‘sin of eve’ the first time she came on, and worst of all…unforgivably worst of all, the girl whose parents never told her a word about periods, and fate decreed that at the age of 10, she would have one. Poor kid..she really thought she was dying.

I lay in bed, musing on these things, feeling my soaked panties clinging to my sex and I rejoiced about how open my parents had been…how accepting when, during the lockdowns, Alison and I started to experiment. When mum and I would have hours of cozy talks in her den about sex, masturbation, fantasies, role play - anything and everything imaginable, no question was avoided, no topic taboo. Sometimes, our discussions would arouse me almost to the point of a spontaneous orgasm…and mum knew. It got to the point where I could, if I wished, simply reach into my panties and finish the job…so, sometimes, would she. 

Thank you for reading this. I know it was horrifically long, and not like my usual style. It was also more m/m. I guess, but I hope you could see the innocence in what Chris described to me. There’s more he told me, but maybe I’ll write about that another time. 

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