Pushing the Envelope

  • Posted on July 1, 2015 at 9:57 am

JetBoy asks…

When did you cross a line, sexually, and how did you feel about it?

In the strange, uncharted territory of our sex lives, we share some pretty memorable experiences — some magic, some tragic, some delightfully nasty — just as the characters in sex stories do.

What I find most interesting as an erotic author is that dramatic instant where a character steps out of her comfort zone, allowing herself to explore something new, unfamiliar, and perhaps a little scary. In erotic fiction, these moments are often what gives a story its most intense excitement… and in real life, such incidents can affect you in a big way, whether for good or for ill.

Thus my first question, for the ladies only (this being a female-themed site, after all): when, if at all, did you cross a line sexually, trying something for the first time that you felt nervous, uncertain or simply curious about? Did the experience leave you ecstatic, satisfied, indifferent, regretful… or unsure, really, of how you felt?

My second question is for those of you who write erotic stories, including my two beloved comrades at Juicy Secrets: when, if ever, did you tackle a sexual theme or practice in your writing that you hadn’t explored before; something that took you outside the realm of the comfortable? Were you happy with the results?

This topic may require some reflection, but I do hope that you take the time to indulge. There are some fascinating ideas to delve into here.


18 Comments on Pushing the Envelope

  1. The most significant “pushing the envelope” thing for me, I suppose, is anal sex. For a lot of people, I think that’s just a standard part of their sex play, but it’s never had much appeal to me. I’ve tried it in real life and just don’t see the point. I don’t like how it feels or how it makes me feel, and so I rarely practice it now.

    In my fiction, my characters usually aren’t interested in anal, and they almost never mention it. But I’ve heard from readers who want me to include that. A few times I’ve sort of dabbled in it, within a story, but it definitely doesn’t turn me on, and so I don’t expect I’ll go there much at all in the future.

  2. Cheryl says:

    Hmm.. Wow, JetBoy, you do pose the revealing questions, don’t you?

    There is one “pushing the envelope” activity I engaged in as an adolescent that has made me feel a bit uncomfortable, but only long after it happened. At the time I enjoyed it immensely, but it has made me wonder if I didn’t cross a line that maybe I shouldn’t have, and I suppose that I only reveal it here because nobody on this site would know me if we bumped into each other in the “real” world. Yes, I’m stalling, building suspense so to speak, but while it is common, it is also considered by many as definitely pushing envelopes. Well, here goes.

    When I was thirteen, I read some porn that included a scene in which a girl about my age had a dog. This girl would let the dog fuck her, but I was not interested in that at all. She did, however, like to put honey on her honey-pot and let the dog lick it off. I had a small mixed-breed dog at the time and I wondered if that would work. She was always sniffing me there anyway, so I figured I would see if I could get off like that. The truth is I never actually came doing it, but it did feel good, and I would masturbate myself to orgasm following the times I did indulge in this activity. It isn’t something I do anymore, but I did include it in a couple of chapters in my “Daughter of a Porn Star” series.

    I received some rather attacking comments about including this in the story, but I included it because it was something I indulged in a bit in my early teens and wanted to explore it in the story, perhaps to come to grips with what I had done back then. Writing for me is cathartic, and I often will include things in my writing to release myself from guilt or some other negative emotion. For example, my first blog post, “Coming Out,” and my story “Finding My Sister” were as much about my relationship with my parents as they were about the fact of my lesbianism or my lifelong desire for a younger sister.

    I suppose I addressed both of JetBoy’s questions in this, although I really don’t see including an episode of bestiality as necessarily “pushing the envelope.” I would say that including girls as young as four would qualify for that, and I do that because I discovered the good feelings associated with my pussy at that age. The truth is that girls that young do not turn me on, though to be honest, my interests do range as low as age six, which is the age of the “fictional” Cheryl in chapter one of the “Daughter of a Porn Star” series.

    Okay, I will shut up now. The truth is when I don’t write, I begin to suffer from insomnia, and being on my honeymoon has curtailed that activity so I am getting that mental release at what is now about 4 A.M. in New Orleans, the city where Lisa and I are honeymooning. Yes, Lisa is blissfully asleep, lucky thing, and no, we will not arrange a face-to-face meeting with anyone in the area. Like Superman, I must not reveal my true identity. If you are in the area, you can just wonder if those two pretty girls walking down Canal Street or in the French Quarter who seem to be in love are Lisa and I. 🙂

  3. Ah, okay, Cheryl’s confession makes me think I should add another naughty practice of my own.

    I haven’t really done it recently, not for several years, but when I was younger, in my 20s, I used to get a thrill from masturbating in a public place where I might be seen or possibly ‘caught’. I never was caught, or observed, as far as I know, but the adrenaline surge from that risk really got me going and I usually was able to climax pretty quickly.

    What kind of places? Well, it began with restrooms at shopping malls, but then I also did it in my car many times, sitting behind the steering wheel in a public parking lot, sometimes with people walking by. I wasn’t really obvious about it, keeping my hand concealed, but then, of course, it’s kind of hard to hide an orgasm when it happens. I’ve done it in parks, like sitting on a bench, although not with anyone really close. I even did it one time in a restaurant, a coffee shop, when it was mostly empty, sitting right there in a booth playing with myself. That was pretty hot. The memory of it makes me think maybe I should try it again, hee-hee.

  4. Cheryl says:

    Yes, Naughty Mommy, you should! Then come back here and tell us about it! I have done this as well, but only 2 or 3 times at the beach, like your character Sheila in “Serendipity.” I sometimes enjoy watching videos of girls masturbating in public places, like libraries where they often will get completely naked, something not even I will attempt.

    Hmm.. Maybe we could both do it somewhere in public, maybe even Lisa can join in, and we can report it back here! Dare ya! 😉

  5. Rita says:

    Oh, I’ve “pushed the envelope” many times in my 54 years
    Anal sex – always loved – still do – having my ass licked along with my pussy. And enjoyed the occasional finger inserted. Years ago I was with a female lover who had a variety of toys to play with. One such toy was a slim finger sized vibrator. Loved the feelings I got when it was used anally Then just gradually began exploring more and more until I allowed my husband to ass fuck me one night, helped along I’m sure with the 3 Martinis and some great pot

    One other example of my “pushing the envelope” is with water sports. First time happened my girlfriend and I were away for a weekend. Again probably fueled by some nice weed and several cocktails
    We found ourselves one night in the shower together when ‘nature called’ and both just went for it.

    I must add that both above revelations are only occasionally enjoyed. Not a regular part of sex with either makes or females. But if the mood strikes just go with it.

  6. Hannah says:

    I’ve pushed a lot of things and had a lot of risky sex in my pursuit of older women, but the thing that really stands out to me was my first time with bondage.

    I was “dating” an woman several years older than me and on our second clandestine meeting she asked about tying me up. I had seen, of course, bondage porn on the net, but outside of some fun spanking I had never done anything like it. I didn’t go for it the first time, but, thinking with my cunt, I agreed the second. Turned out she was a very light Domme and I was actually kinda disappointed. I thought I had bondage licked and then the next time, with another older woman, I ended up black and blue.

  7. ThylaneLover says:

    Well since I’m not a female I can’t answer the first question about pushing the limits.

    As for the second one though, I wrote a couple of stories that involved some unpleasant things being done to the minors involved. Nothing gory, but definitely non-consensual.

  8. Lou says:

    I often go to the cinema on my own and really enjoy pleasuring myself knowing there are people near me x

  9. kim says:

    true confessions time,since the only person here who knows me in real life knows all this anyway.
    age 12, let a dog lick my pussy, only once, but it seemed like a good idea at the time,never done it since.
    age 10 summer time had drank a lot of water as had my best friend, we were outside in our swimsuits and had to pee,took turns laying on lawn, while the other stood over the other ones midsection legs spread and without pulling aside our swimsuits just peed.only time ever did any water sports,no interest in it.

    age 9 to this very day, standing in a pool where the water jet thing pushes,and I love the way it hits my butt hole,makes me horny.

    age 8 to this very day, getting naked or exposing my self to a friend,outdoors.

    from age 10 to this day, having my lover tell me to undress,and masturbate in front of them.

    age 18 to this day, getting a play spanking.

    age 10 to this day, some anal play, rimming, insertion with an object or finger.

    OK now you all know what a super freak I am, the things I still do, I don’t do often, but sometimes it just comes up at a good time for some special fun.

    Some people may think that coming to sites like this and masturbating to these sort of stories is pushing the envelope also,so I guess we are all in good company.

    • Larry1863 says:

      I love all those things and I’m a guy and have done several. Wonderful that you got to live it and like most of it.

  10. Lou says:

    You’re not a super freak at all Kim and I think it’s the fact that we can understand each other that makes this such a great site x

  11. ThylaneLover says:

    @Kim – Like Lou said, you’re not a freak at all. What turns people on sexually is a matter of personal taste. As long as no one is causing another person unwanted harm, then have fun.

  12. kim says:

    yes, well I am having fun, just saying like Jet Boy suggested what I have tried and what I liked and didn’t.

  13. John says:

    Hi my (assumed) name is John..this is my first post on here so please bear with me 🙂

    Reading the title of this post reminded me of my youth so I thought I would share to see if any others ever did anything like me when they were younger

    I started when I was probably around 12 or 13
    Growing up in a large family with older brothers & younger sisters getting time to myself were I could experiment with the growing needs between my legs was extremely difficult. So I started to take myself off to the woods surrounding our small village to release my pent up frustrations
    I would usually find a quite secluded spot under a tree surrounded by bushes so I would not be disturbed while I stroked myself to a satisfying orgasm thinking about a girl I knew at school who looked so sexy with her long blonde hair flowing down her back and her ever so short school skirt that use to fly up as she ran around the play ground sowing off her beautiful legs and her tight white knickers .
    One day while I was in the middle of a prolonged work out under my favorite tree I heard a noise not far away from where I thought I was hidden from the world and when I looked around slowly so as not to draw attention to myself I spotted a woman walking her dog ,she looked to be around my mums age (mid thirty’s) and had not noticed me hiding behind my tree so been the horny young lad that I was I carried on masturbating while discreetly watching this lady walk her dog not more than 30 feet from me completely unaware of my actions so close to her .This lead to one of the greatest orgasm’s I had so far as a youth and I came so hard while looking at her walking away across the fields with her dog ..After that I would try and time my foray’s to the woods to see if I could see this lady who had become the object of my fantasy’s ..
    Several weeks went by with out me spotting her again when one day I was sat in my usual spot under my tree jeans pushed down around my knees with my hard little cock in my hand slowly stroking away when I became aware of someone watching me..I looked around and there not more than 10 feet away was my fantasy lady minus her dog watching me and smiling ..I quickly panicked and tried to pull up my jeans and hide my cock from her view (which if you’ve ever tried to stuff a rock hard cock back into tight jeans while sitting down is pretty hard thing to do lol) she then spoke and said ‘don’t panic I’m not mad at you I know you sit here quite a lot playing, I’d would like to watch you finish what you were doing and not to put it away’ after several tense moments and soothing words from the lady I slowly took my not quite so hard cock back out and started to stroke him again all the while watching the lady watch me ..she never did anything other than watch me (I often fantasized later in life that she would have come over and stroked me herself or even sucked me off but that never happened) shortly after I started I shot a load of cum all over by stomach and legs as I looked straight at my mystery lady ,who then smiled and said goodbye and just walked away leaving me to clean up a rather big mess ..I wonder if she went home and played with her pussy thinking about the very young boy she had just watched cum for her in the woods that day ?
    To this day I still, when I get chance, like to masturbate outdoors where I might get caught although I have to be very careful now a days not to get caught and labeled a pervert ..

    Anyway that is/was my “pushing the envelope” experience

    I hope you all excuse any error’s in my typing

  14. Dabbler says:

    Just discovered this great forum. Thought I would add my little (true) story.

    I discovered cross dressing when I was about 13. It was a strange and more or less completely heterosexual thing for me and was somehow about exploring the then hidden territory of the female form. I had no idea what a ‘transvestite’ was, or even that was what I was doing. I did have a sense that it was somehow kinky, but this was a very long time ago and kinky wasn’t really much up for discussion, let alone if you were 13! It just felt sexy and it always ended with masterbation. I was a bit on the chubby side and would truss up my mini man boobs to look a bit more like real breasts, tuck my little cock between my legs and find something to wear of my mother’s as I recall. Can’t remember what for the life of me.

    We used to travel by sea a lot around Asia and Australia as my parents were expats and on this particular occasion we were on a Norwegan cargo ship which carried just twelve passengers (I later learned it was for some odd tax reason). There was a young Norwegian woman in her mid 20s on board who I thought was stunning. All the adult males seemed to be besotted by her, as was I.

    One day I was in my cabin doing my transvestism thing when I noticed a shadow on the slatted vents on the cabin door. You could open and close them and I had foolishly left them at a slightly open angle. I went the the door to close the blinds and to my horror the young Norwegan woman was there, just disappearing round the corner because she knew I had noticed her. My shame and embarrassment was indescribable and were made even worse by the fact I had no idea why I was doing this and what it could be about.

    Thing was we all had meals together with some of the ship’s officers and that night and for another week or more I had to sit there imagining her eyes boring into me and wondering what sort of really weird kid I was.

    I grew out of this behaviour more or less once I got to explore the bodies of real life girls, but there has always been a bit of this big, rather hairy older guy, who would have loved to have experienced being a young girly girl. I have also always had a deeply kinky side to my nature.

  15. Saapho69 says:

    Are you all ready for my sexual confessions? TBC

  16. Saapho69 says:

    Some of you may not know this about me from my posts, but Im a slut and I love it. clears my throat.. Hi Im Jesse and Im a sex addict lol. I am a very sexually aggressive women, Ive been told I have the sex drive of a man. That’s insulting I have the sex drive of 20 men or 1 women :P. Its not that Im adventurous, im just a pleaser. Im willing to try most things once to please my current lover. because that’s what I do lol.

    Age 10-11.8 u know about my sister I posted that elsewhere, had I known this was here Id have posted it here lol.

    Age 13 First time I had foot sex, I had a 16yo Gf and she had seen this porn where the girls sucked each others toes and fucked each other with there feet. So we licked each others toes, it felt good and it was nice enough, then we set across from each other and penetrated each others pussy with our big toes. eehh it was okay like a fat finger or something. but she loved it so of course being a pleaser I did it a lot for her. Haven’t really done it since then. Now Im fairly dexterous with my toes because of all the practice grabbing her clit with my toes lol

    Between 14-15 I was in the hospital for a year healing and rehab from an epic tragedy (don’t ask I wont talk about it, at least not until I know u ALOT better lol). I met a 25 yo nurse who would always tease with me, I just thought she was being nice. Nope she was horny for this 15yo Bod. One day she cornered me in the rehab center and just asked me if I would be interested in having sex with her. My answer after the break lol…… of course it was yes. She had watched me enough she wasn’t worried about asking she figured Id say yes (she told me that later on). That was my first adult/child sex and I was the child. btw it didn’t give me any negative effects no nightmares… In fact it helped me get through some shit. It was great, later she got fired not for pedo but for stealing meds. Never saw her again. Probably went to jail.

    We jump to 18 and college. My first 3some and 4some with my girl posse we called ourselves Sapphic Angels (the ones im going on the cruise with in April.. more 3 and 4somes lol). Loved it do it any chance I get. Also my first anal sex with a strapon (I don’t get strapons if I wanted a cock id go find a guy lol). any way one of the Sapphic angels liked to fuck girls in the ass and once again enter the pleaser lol. It was okay, but if I do anal I prefer a plug or a tongue a finger or a small vibrator (side note if a mans penis could vibrate as fast as a quality vibrator id find a man lol). My first piss, again another porn yadda yadda yadda, needless to say we pissed in each others mouths and on each other. Why u ask.. say it with me Im a pleaser lol. I enjoyed aspects of it a lot but overall it was good enough id do it again for a lover. I draw the line at feces pleaser or no, noway in hell. Public sex: me and one of Sapphic Angels got horny teasing each other while goofing in a park on a crowded labor day weekend. We went behind some bushes, started to have sex got caught went to jail for public indecency paid a fine will do again and have. (actually I like public sex, I had public sex last Friday at the club in a car parked on the street outside, saw several camera phones outside the window, might be on the internet by now) Do u have no shame women? NO NO I DONT lol). Im not worried about it because Im already on the internet on a milf site (that’s another story, which I will tell somewhere but it wasn’t sex so it doesn’t fit here) Before u ask I have paid many fines for public indecency. Lots of other experimental sex nothing id say was to deviant or erotic. I would tell u about it if u want.. why.. because Im a pleaser lol.

    Age 31 my first time with a minor. She seduced me… no seriously she did.. I see that look but she did.. quit laughing she really did… okay fine it was mutual. A friend of my daughters saw me asleep in my bed, she really liked me, I was practically naked. Next thing I know I woke up to her licking my pussy. Seriously who’s going to say no to that. raise ur hands. I didn’t think so. I see those looks.. ur jealous lol. jk. Yes I think u know if I would do it again. im here on this site nuff said.

    oh I learned to squirt in college but that’s not erotic or anything. You can guess who taught me how… yes one my angels. hey I like that Jesse’s Angels, ill bring that up in April lol.

  17. Saapho69 says:

    I forgot in I also had my first orgy, it was the Sapphic angels and group of sorority girl (BTW they weren’t lesbians and wanted nothing to do with us lol) who invited the 4 of us to a party that was just them and us. We weren’t sure what was up, but then the leader came up to Alana and said want to fuck and kissed her. Well it was on then and we did all night. With those anti-lesbian sorority girls lol. have been in orgies since and wont stop (afterwards they went back to being snobby bitches and anti-lesbian lololol).

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