Home > Blogs > sissyCDisback > just can t give up this lifestyle! Love it too much to walk aways > Blog Post

My first attempt at anal!!!

11:27 pm Wednesday, 9th May, 2012

I've finally - after many MANY years of searching desperately to lose my virginity, fantasising on getting the chance to be penetrated in my tight virgin arse - had my first attempt at anal, but UNFORTUNATELY am no closer to actually losing the virginity status of my name!!! Although I DID manage to break some virginities recently, and on hindsight the experience was STILL totally horny (I've had many wanks reliving the experience, thinking what could have been), I still am no quite there! I had heard about a gay cottage local to me in Hoddesdon, and had ventured there on many occassions but had no joy. The frustration of venturing out, hoping to finally get cock, but returning with just cheap wank is always a real let down! And on this occassion it started very much the same - I had also been to the shops & bought a new suspender belt, lacy knickers & stockings and when I got there there was yet again no one around. Frustrated & horny I decided to put on my new lingerie, hoping that if anyone did come in that they'd get a (hopefully) nice surprise! I quickly put on the stockings, and the horniness as I slipped on the silky stockings as always made me feel absolutely horny. I put on the knickers and was just starting to wank when I heard the door go in the cubicle next door. I fiddled with my suspender belt & slowly started to wank myself through the lacy knickers when I noticed a smiling face poking over the top of the cubicle! They asked if I wanted a hand, and I was quickly in their cubicle with them. After my last failed attempt in a cubicle, where I got scared & rushed out, I was determined to see this through to the end! They asked what I was after & I explained my complete lack of experience but that ultimately I wanted to suck cock, to then feel cock slide & pound in my tight virgin arse, and to then taste their cum (so not epecting toooo much?!) - but that I was a nervous virgin, but needed cock sooooooo bad! They said to not worry, but that they liked my stockings & wanted to suck me & that they'd been with other virgins so would take things gently.

I soon had my cock out & they quickly had me all the way down their throat - they were a complete expert cock sucker, and the feeling of having them suck me off whilst in my lingerie was amazing. In fact it was my first experience dressing with someone else, even if it was just stockings & suspenders with my trousers around my ankles! The feeling of being in a public toilet, getting an amazing blowjob, whilst I was wearing lingerie knowing I could get caught at any minute meant that I was very soon near to coming, but they stopped & said that they wanted me to suck them off. They said that in their experience if a nervous virgin had cum, then they'd be more likely to want to leave withou returning the compliment so that I should suck them off first!!! hilst desperate to cum, I didn't need asking twice, and was very quickly down on my knees. This time I felt I was a more accomplished blow-jobber, having only ever sucked cock once before!!! I started by slowly licking the tip of their cock, and then licking all the way down to their balls, and then gently placed my mouth around their erect & gorgeous cock and slowly moved my mouth all the way down their thick shaft. I went a deep as I could & held it there for a while, savouring the feeling of their hardness in my mouth, and then slowly brought myself up - moving up & down sucking them off. I was determined to ensure that this blow job was better than my last, and looked adoringly into their eyes to ensure that they were at least (seemingly!) enjoying it - the look in their eyes seemed to show that they were!, so I decided to gently caressing their balls and then finger their arse. I then tried to deep throat them,by moving slowly dwn their cock until I was as deep as I could go and I did not choke neary half as much as last time & was no way near as nervous. On my last attempt at a toilet bj I ran out panicking after 5 mins, but this time I was determined to finish them off!!! A combination of my sucking, licking, wanking, and deep throating soon had them groaning in ecstasy (or so I hope - I'm sure it was not boredom???!!!!), but I didn't yet want a mouthful of cum but was DESPERATE to lose my anal virginity.

I asked them if they wanted to fuck me & they said yes, and I again explained I was a virgin. There cock was about 7" but thick, but I was sure I'd be able to handle it & was desperate to try! They asked me to turn around, and & said they wanted to rim me - I'd never had this done before, and the feeling as they slipped their tongue in my virgin arse & then fingered me soon had me begging for them to fuck me. I was gagging for cock & was desperate to finally lose my virginity after all these years of fantasising & trying. For a brief moment I thought of my wife & what would happen if I was caught in a toilet wearing gorgeous stockings, suspenders & lacy knickers with a cock deep inside me but I knew that this WAS the moment I'd be looking for many years, and that I needed this more than anything in the world. BUT just as I'd got a condom on them, someone went into the other cubicle - I was sooooo horny, yet scared about being caught. But they quietly told me to suck them off again, so I got back down on my knees and started sucking them through the condom. They held my head just at the tip of their cock, and I slowly and gently just sucked & licked the tip of their cock, and they'd then pull my head down so I was deep throating them, then they'd want me to just suck the tip. They were soon forcing my head down deep over their cock so that it was deep down my throat, and quite forcibly held me their until I could take no more - the forcefullness of being mastered & dominated was a complete turn on!!! Soon (though it felt like ages as I tried to suck cock quietly) the other person had gone, and I was bending over, eagerly waiting their cock to penetrate me.

They slid their cock up and down my arse a few times, trying to part me gently and then lubed me with their saliva. They quickly penetrated me with a few fingers which was the most amazing feeling, and then slowly pushed and entered my tight virgin arse. I'd used dildos before (be it not for a while as I'd thrown them out, panicking the wife would find them!) but was not ready for it & it popped out again & again. They tried again, this time holding it in me so that I could try to slowly push down on their cock. I did manage to get it in me, and they did slowly thrust in me a few times, but the pain was far more than I'd ever imagined or experienced with far bigger dildos!!! I tried again one final time, and slipped my arse down their cock as they held open my anus, and did managed to get it in quiet far but I just couldn't keep it in or get it in properly. They suggested we stop & said that the nervousness of the cubicle & the anxiety of losing my virginity meant I couldn't relax and that it really didn't matter, but I just know they were being nice!!!! I felt horny & disappointed that I hadn't lost my anal virginity, and was soooooooooooooo annoyed. I turned around, and took off the condom & said that the least I could do was suck them off! So slowly I took their cock in my hands & slowly slid my mouth down their no doubt desperate to cum cock! I was once again back sucking, deep throating & licking the tip of their cock as instructed, whilst also caressing their balls & massaging their anus. Soon I could sense they were coming & looked up into their eyes as they gave me their cum face, and me a face (or mouth!) full of cum. This was the second time I'd swallowed cum, and this time they were a heavy cummer as there seemed to be sooooooo much more than on my first time! It seemed to go on and on, as lashings of juicy cum seemed to squirt for ages. But again I managed to take it all, and to swallow & savour every last drop. The excitement of actually tasting more cum, especially whilst dressed in sexy lingerie was amazing & I was desperate to cum. In fact I'd leaked precum everywhere! They said they wanted me to fuck them, and although I am a complete anal virgin - and never even given anal with my wife or previous girlfriends - I said I needed to go, as I was now scared of getting caught - so left having had the chance to lose both my anal virginities but succeeding in none.

I drove home in my lingerie under my jeans & was the most sexually frustrated I'd ever been as I felt I'd lost my big opportunity to feel cock in my arse. I have probably dreamt & fantasised of this for 15+ years, and actively saught this on various websites for more than 3-4 years, so felt AND STILL DO that my real chance of sexual utopia had gone. People on this site & others had said my first time WOULD be painful, but that to try to push through it so to speak and to relax! But I felt like I'd failed! I wish I could be in that situation again & just to relax through it, to grin & bear it, to think of the end result of feeling cum gush in my arse. In hinsight I HAD got to taste & savour cum for a second time, got to suck cock in a seedy toilet, got rimmed for the first time, and finally got to dress in lingerie with another person whilst sucking cock & tastin cum, and to feel a cock in my arse (even if only for a short painful while!!!).

As great as that was I still feel like I've lost a great opportunity especially after all these years of really trying , and just hope that another one will occur soon again.

Perhaps if you can accomodate (rather than a seedy toilet) then I can relax more, then I WILL finally get to feel cock pump in & out of my tight virgin arse.I need this more than anything, and it truly is ALL I can think of! I DO promise I'll try not to let you down, and will do anything & everything to finally get to be fucked like the sissy that I am. I cannot wait! PLEASE HELP!!!!!!



Comments
4:04 am Thursday, 10th May, 2012

wow love the storyimg src="imagesadultemoticons019.gif"

5:21 am Thursday, 10th May, 2012

img src="imagesadultemoticons011.gif" img src="imagesadultemoticons011.gif" img src="imagesadultemoticons004.gif" img src="imagesadultemoticons002.gif" img src="imagesadultemoticons030.gif"

1:07 pm Thursday, 10th May, 2012

It was exactly my dream, Ive not made it yet. Good on you.
Maximg src="imagesadultemoticons005.gif"

12:11 am Friday, 11th May, 2012

great story :)

8:03 pm Saturday, 12th May, 2012

amazing story :)

9:24 pm Monday, 14th May, 2012

Fabulous story.
Get yourself a plug to put in when you go out in panties & jeans again. that will help keep you open and receptive.
And do yourself a favour darling and pack some lube in your handbag.
Hugs
Sammiimg src="imagesadultemoticons029.gif"

Blog Introduction

just can't give up this lifestyle! Love it too much to walk aways


Get full access to all site features
Register Now