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The sister then the brother
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By (user no longer on site) OP
over a year ago
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Few years ago I was drinking in my local and there was a girl who came in blonde hair, petit, strange but attractive face if that makes sense, she had an amazing body all over, normally I notice most women either have tits or an ass but she has both!
One of my mates I've known since school says was playing the fruit machine in the corner (think they're called bandit machines on the mainland) he seen Her come in and was all over her like flies around shite lol but she wasn't really having it.
This mate of mine was well known to fuck everything and anything around him, also he had a gf, most people knew that as well, so she said she had a boyfriend to get him away, I overheard as I was playing the pool table nearby, I said to her after he walked away "that was a good one, u don't really have a boy right?" she was embarrassed face red and said "how do u kmow that?" I replied "because from when you've walked in u haven't stopped staring at me"
Immediately I could see she was thinking 10000 thoughts at once and trying to get a good response but I saved her the hassle and just said, "it's alright I've been thinking about what we could get up to when we leave here together"
I could see straight away she was loving it, she went from maximum embarrassment to horned out of her mind in the space of a sentence, she told me later that actually got her wet, so we fucked about in. The bar for a bit kind of like going through formalities then... |
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By (user no longer on site) OP
over a year ago
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At this moment in time I was training in the gym 4 or 5 days a week, taking steroids, doing tanning beds, had just grew out a nice full beard and I was getting attention like I'd never had before from women, so this girl in my eyes was just another lock to pick but I did tell her before anything on the way to my place that I'm not looking for anything serious
I said this to alot of women around this time because I thought if I was honest then the next day it wouldn't be bad if. I'm not really texting. Them etc but never worked out that way! After fucking they always got attached!
So anyways I brought this girl back and had her twisted every shape, she was a pretty vanilla girl in bed so when I had her all over the place she didn't really have a clue what was happening but didn't really matter as I just took the lead and fucked her every way I wanted, I had her lifted at the end she was holding her arms linked arojnd my neck with her legs up at my head if that makes sense, kind of like a cradle and. I was just pounding the shit out of her and she was completely soaked, I came inside her while still holding her up because she told me she had the implant and so I sat down on. The edge of the bed still holding her and she was still arms linked around my neck
I looked down and there was blood everywhere, she'd just took her period while we were doing the business, definitely wasn't before as I had a full frontal before we started, so obviously she was embarrassed but I. Told. Her. Don't. Really care its just blood, we sorted it then went to bed
The next day.. |
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By (user no longer on site) OP
over a year ago
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So the next day, we got up fucked again didn't really care about the period because we'd already done. It the night before she didn't care either had a domino's then she went on her way in a taxi
Later that day she was texting wanting to come down and do this and that but I didn't want to just told her I'd things to do as didn't want to straight just reject the girl, but this went. On for like a week or 2 before she realised something more wasn't going to happen, she was a really nice girl BTW had a job in. Which she was helping people every day, she was smart and had goals for the future but we just didn't click, after sex it was just like "so what now?" lol I'm sure you guys have felt that before, where you feel like you need to force conversation?
So fast forward like a month and I'm in the bar again and. Her brother is there and he's gay I've drank in his company before even been to a few parties in houses and he was there but we never really spoke.
That night we spoke a bit in. The bar and I told him I'm. Sorry about the way I was with him. Sister
... |
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By (user no longer on site) OP
over a year ago
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He said to me that it wasn't nice because she really liked me etc but I told him that from. The start I told her that wasn't looking for anything serious it kind of got left at that and we ended up going to his apartment with a friend of mine, at that time I was fighting with my girlfriend and had to stay in my mums house but it was late like 3am at this point and I knew they'd be sleeping and didn't want to wake them
I said this to the brother and my mate who was about to leave and the brother said I could stay there because he's had an extra bed, now at this time I was on and it always made me really horny and that's when I would usually go hunting for trans women, but I'd never let a guy do anything with me before
So when I agreed to staying I had no intention of doing anything with the brother but I'd soon find out he was setting up a situation for us to be alone |
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By (user no longer on site) OP
over a year ago
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So keep in mind I've always been a lads lad, even now no one knows I've been with trans women and at thay time me and the brother were getting more fucked up on. The drink and white stuff and he just started talking about how his sister told him I had an amazing cock and I was the best fuck of her life
I kind of didn't know what to say because what do u say in. That situation so I joked and said something like "Well I do try" and laughed a bit and he just came out with "I'd love to suck your cock I heard its really fat" |
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By (user no longer on site) OP
over a year ago
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I told him straight and still to this day dunno why I did, because this guy knew alot of the same people I knew and could've committed social homicide on me because the crowd I was. In with would've just tore me to shreds if all this came out but anyway I told him I'd actually been with trans women before but I couldn't be with a guy because I'm into the feminine look
I explained doesn't matter to me what gender you were born as, if you look feminine enough then it gets me going.
So at this point he says that he has makeup, wig, clothes etc all there because he does drag and asked me if he got dressed up would I let him suck me.
Didn't take long for me to agree to the proposal |
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By (user no longer on site) OP
over a year ago
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So I agreed but said he has to look fem enough and if he doesn't then I couldn't do. It so he spent like 20 to 30 mins getting ready and came out
He looked like u would expect, everything just threw on and rushed a bit of a mess he actually looked like he had been fucked hard already lol hair a mess makeup smudged, lipstick going onto the face from lips etc so I said I couldn't do it and immediately he said I've a dark room with a chair you can just sit there and let me suck you
Because I was pretty fucked up and also he did look alot more fem I agreed, he actually sucked me for around 2 hours straight and he would've kept going if I let him, he was alot better with his mouth than his sister and I actually told him that at the time lol |
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By (user no longer on site) OP
over a year ago
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So we went to. His bedroom at. This point the sun was coming up because it was like 7am but when I had him bent over on all fours. On. The bed, the wig, the shape of the body and the little short skirt lifted up really got me feeling like this was a really little sissy so I was ready to rock
I'd been walking around naked for ages since. The dark room stuff but only noticed when I looked down at my cock getting ready to push that it was. Covered in red lipsticks on parts of the shaft and. That really got me going big time
Red lipstick for me is seen as really trashy and I love that, I love the trashy look like hoop earrings, blonde wig, red lipstick etc just things that scream whore so at this point I went to stick it in then just as I was about to do it I avtually said, "you know what, loosen yourself up before I even go near it, I want you to be begging for it and then ill decide whether I want to or not" at this point I was clearly getting into all this.. |
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By (user no longer on site) OP
over a year ago
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So at this point I lay back and he, well she now, started sucking me off again while fingering her own hole and kept asking every. What seemed like 30 seconds for me to stick it in.
After like 10 mins of this I decided I was ready to get down to business and just flipped her over pushed her head down made sure the ass was high and just pushed straight it with one motion and she cried out with both pleasure and pain, I could feel she was loosened up so I just went fast from. The start and stayed. In. That position, I had been sucked for a long long time so I just wanted to finally unload and after what seemed like forever to me. I finally did |
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By (user no longer on site) OP
over a year ago
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I forgot to mention we fucked raw because I knew him and I knew he wasn't the type to fuck around with everyone and because we had alot of mutual friends I would've known if he had anything, some people might not agree with it but that's the judgement call I made at the time
And I was glad I did because the best part of the whole experience was watching her boy pussy still up in the air and my load just drizzling out and there was tons of it, she just lay there in that doggy position for around 5 mins and I said do u want me to get a towel for the cum, she just replied no I want it all over my bed
Might sound funny but I was thinking, OK then no probs because I wasn't planning on staying lol, I'd finally got my balls emptied and although I could've went again it took me so much pumping to. Finally blow so I knew another attempt could possibly make me go into cardiac arrest 
It was actually after this sexual adventure that I decided to start doing cardio at the gym lol, was kind of embarrassed with how heavy my breathing was after and I just about managed to finish
But anyway, I said to. Him he was a better fuck than his sister and his bjs were miles better lol, and this. Just reaffirmed to me why I love trans women, I get. The attraciveness of the feminine form but the sexual skills of someome who has years of experience with a dick best of both worlds, the only downside is. I could never go public with it although sometimes I've. Fantasised about going on a date with an extremely passable trans woman and nobody realising |
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By (user no longer on site) OP
over a year ago
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I've lately seen some amazing trans women that obviously started hormone therapy in their. Teens and. They've came out looking better. Than most women I kmow, and a big part of me would love to take one of those beautiful women out in public and nobody having a clue then eventually reveal it when a load of friends. Have said how gorgeous she is etc lol
I know personally alot of men do have secret feelings about say ladyboys etc when their travelling. Show comes to. Visit but they're just scared of being judged
But anyway about. The brother, he actually told me before we really got. Into it and. He got. Changed a load of names of people I knew who had tried to get with him and I was shocked because they were people you'd never expect, weird how at thay time thay didn't put me off messing around with him because he so easily said others names so he could easily say mine, but he never did, I was paranoid so much though for weeks after especially about the pics on. His ipad for grindr and my friend who left us to. Go. Home joked with me when. He seen me and said so did. He try suck your dick and I just laughed it off like "no he knew not to try it mate" but I seen. Him shortly after in the bar again and. He was. With his sister and it was a weird feeling sitting close. To them knowing I'd fucked the both of them and wondering if the sister knew
Part of me was thinking did the sister get the brother to get with me to try get revenge for me ditching her but nothing ended up happening, the brother as well became kind. Of attached and. Would call me when drinking wanting me again but I decided not. To as was too risky in my eyes |
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By (user no longer on site) OP
over a year ago
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The thing was the brother lived in a block of apartments where a good few people I knew lived so all. It. Would take is someone to see me coming out and. Put 2 and 2 together as they knew me. And. The brother weren't really close
I had in my. Head though that I could say I was returning his sisters phone charger
I also had up my. Sleeve that if. It came. Out about what I done I'd just say its made up because I ditched the sister and because of my. Image of a lads lad most people would believe me
Til this day no. One in my circle knows about my escapades and sexual adventures and I've a load of experiences through the years lol but this is probably one of the weirdest yet hottest depending what you're into
I have a story about a time I fucked a lesbian who hadn't been with a guy for 10 years, that's another good one lol maybe tell it another time if there's interest
Everything in this story was 100% true, the only. Thing wrong would be some of the things said because it was years ago but i wrote it as close as I could remember lol
And I wrote this story because I was going through Facebook looking up people I've fucked and seeing how they look now and I. Thought of him and his sister lol |
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actually felt like I was writing that for hours lol