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Caught crossdressing led to first ever threesome with housemate and her bf

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By *eelslover300 OP   TV/TS
23 weeks ago

flitwick

About 10 years ago I lived with a girl I worked with (same graduate scheme). I had dabbled in crossdressing since I was young but this was the first time I had real genuine freedom to do it and had started to buy a few things myself. Anyway one day I had gone to someone local who had been advertising on fb marketplace and had come back with a black bag of shows and clothes. I rushed straight to my room to try them on and have some solo fun. Thirsty work so I quickly rushed out to the kitchen to get a drink and in that time I heard the absolute crushing sound of the front door opening. There I was in the kitchen, stockings, heels, lingerie and my housemate was effectively now between me and my bedroom with her bf. I stood there hoping they would go straight to their bedroom and considering do I quickly strip completely naked rather than be seen dressed... I didnt have time for that as both came into the living room and saw me stood there in the kitchen...

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By *hastity_roseTV/TS
23 weeks ago

Nowhere

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By *lljambarMan
23 weeks ago

Manchester

good start

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By *ancSissySlutTV/TS
23 weeks ago

M66

Good start x

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By *rishman30Man
23 weeks ago

belfast

Very promising

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By *teve1867Man
23 weeks ago

wirral

Can't wait for more

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By *till HandyMan
23 weeks ago

Redruth

I’m liking this ..

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By *eelslover300 OP   TV/TS
23 weeks ago

flitwick

It was all very awkward. I felt like I was redder than the reddest tomato. Just stood there in lingerie and heels whilst they looked at me. Eventually my housemates bf broke the ice a bit and said "you look pretty hot". My housemate (ill call her Katie from now on) jokingly asked him if I looked better than her when she dressed like that. He said no but he wouldn't both of us dressed like that. She and him disappeared for 2 mins and I just stood there, visibly shaking and starting to play things in my head like what if she tells people at work, what if she tells my parents when they visit. She returned without him and told me to get all the fem clothes I had and go to their bedroom.i grabbed by black bag and another large carrier bag of stuff into their room. Katie shut the door behind me so her bf (call him Alex) was left outside to put their shopping away. She emptied the bags on to their bed and said something like lets sew what we've got to work with. With her guidance I tried on a few things and ended up in a red set, a short leather black skirt and she let me borrow a red top of hers. I was sat there in the outfit on the edge of the bed still no idea what was going on and I didn't know where to look when she literally just pulled her top off and took her jeans off. She was getting changed too. Out comes a red set too, black stockings similar to the ones I had on, and finally a short black dress. She opens up a drawer under her bed to reveal the holy grail. Heels! About 10 pairs! She asked me which pair I think would go best. I picked out a patent black pair. Basically the same as the heels she'd picked out for me but mine were red

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By *ntman83Man
23 weeks ago

Walsall

Good start

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By *hastity_roseTV/TS
23 weeks ago

Nowhere

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By *angtidy42Couple
23 weeks ago

Redditch

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By *eewilliewinkieMan
23 weeks ago

Stirling

Hot so far

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By *andg1981Couple
23 weeks ago

Aylesbury

Good story so far

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By *harlottes ChurchTV/TS
23 weeks ago

Toy me town

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By *eelslover300 OP   TV/TS
23 weeks ago

flitwick

She grabs me by the hand and we open the door and call Alex in. He walks in and just looks at us up and down. They kiss as I watch and she undoes his jeans. She drops to her knees and pulls me down with her. She puts my hand at the top of his boxers and together we pull them down. Alex is already very visibly excited and that only grows when Katie starts to lick and suck him. After a minute or two of her readying him she grabs him and moves out of the way a bit and invites me to try him. I look up at him and he nods. I taste him for the first time. I start sucking him with Katie watching, very occasionally getting a taste herself. I almost gag in one moment and it was then that I realised I was living the dream. Katie started kissing me. Now Katie is super hot in my opinion and I wouldnt say I had fancied her given I knew she was in a relationship but to see her in the outfit she was in, on her knees sucking cock and now kissing me was lets just say almost too much! We kissed for what felt ages with Alex's cock just hovering above us. We did eventually turn our attention back to him but it wasn't long until I felt Katie's hand going up my skirt. I was undeniably rock hard at this point and she told me to stand up with Alex. She compared us both and started sucking me and wanking him. He then told her we need to get on the bed so he could fuck her. She got into doggy and he went behind her and they started fucking. I wasn't sure what to do until Katie grabbed my hand and pulled me close. She told me to take the top and skirt off which I did and she started sucking me whilst she was being fucked by Alex

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By *rishman30Man
23 weeks ago

belfast

Amazing xx

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By *hil911Man
23 weeks ago

Solihull

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By *j and c 2Couple
23 weeks ago

mullingar

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By *lljambarMan
23 weeks ago

Manchester

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By *issyrachelukTV/TS
23 weeks ago

Bilston

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By *rinwin69Man
23 weeks ago

STOCKPORT

Excellent

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By *eelslover300 OP   TV/TS
23 weeks ago

flitwick

He was clearly close to cumming and she asked him if he'd be ok with me fucking her. He duly obliged and me and him swapped. Her sucking him whilst I fucked her (all raw). She had already cum from him and was now cumming again with me inside her. Alex wanted to cum so Katie asked me if I wanted his cum. I asked where he'd like to cum and he said my face. I had never had a facial but it was a very quick yes. She laid me on my back on the bed and with great skill in her heels proceeded to ride me. He positioned himself above me at the side of the bed and with a few sucks and and strokes he released all over my face. Within 15 seconds Katie's riding had made me cum inside her without even a chance of warning her (I still wasn't sure about tasting cum and didn't want to open my mouth). There she was sat on top of me with my cock still inside her, Alex's cum on my fave still and I didn't know what to do. Eventually she got off, Alex had got me a towel and I cleaned up. We ended up laying on their bed chatting about the sex, about my dressing, about my only 2 previous experiences with a guy

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By *ndrea54TV/TS
23 weeks ago

cambridge

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By *j and c 2Couple
23 weeks ago

mullingar

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By *eeker of pleasureMan
23 weeks ago

manchester

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By *ornyabdnguyMan
23 weeks ago

inverurie

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By *hastity_roseTV/TS
23 weeks ago

Nowhere

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By *till HandyMan
23 weeks ago

Redruth

Mmmmm….so hot !

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By *inkyfuntimesMan
23 weeks ago

Northampton

Loving this story !

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By *J GeminiTV/TS
23 weeks ago

Northumberland

Very, very hot indeed ,

Xx

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By *erry bull1Man
23 weeks ago

doncaster

Hot

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By *aughtyNikki100TV/TS
23 weeks ago

Doncaster

Ooh this has much potential x

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By *iker197Man
23 weeks ago

Hinckley

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By *istresskaty1981TV/TS
23 weeks ago

brigg

Wow love this!!

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By *eelslover300 OP   TV/TS
23 weeks ago

flitwick

A couple have asked privately is this a true story. It is 100% true with the only things not true are the names I have used!

Katie became a fwb and given we lived together we hooked up daily after this and 9 times out of 10 if Alex was there I would join in some form rather than then just doing it alone. Unfortunately Katie moved out 2 months later and the threesomes pretty much dried up straight away but her and I still met up a few times with her coming over but I had a new housemate so dressing with her was confined to my bedroom again

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By *rishman30Man
23 weeks ago

belfast

Sounds like such a horny experience and well written xx

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By *ark_sentinelCouple
23 weeks ago

Andover

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By *en4funoxonMan
23 weeks ago

Banbury

mmmmm

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By *ose3545Couple
23 weeks ago

wicklow

Great Start xx

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By *igkidexyMan
23 weeks ago

Dublin

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By *he jesterMan
23 weeks ago

Carmarthen

Sounds fantastic

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By *J GeminiTV/TS
23 weeks ago

Northumberland

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By *urabriteMan
23 weeks ago

stafford

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By *ell18TV/TS
23 weeks ago

Mkt Bosworth

Loved this Story

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By (user no longer on site)
23 weeks ago

Sounds an amazing story and one that only few get to act out.

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By *ylon_cMan
22 weeks ago

Dunfermline

Sounds pretty hot

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By (user no longer on site)
22 weeks ago

Hot story !

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By *ressuploverTV/TS
22 weeks ago

Cardiff

Very hot!

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By *alm_one4Man
22 weeks ago

RM16

Bookmarking

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By *exymarvelMan
22 weeks ago

cardiff

The dream

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

After me and her hooking up a lot after and several times with both of them they broke up. She came over a few times after they broke up but one Sunday after she stayed over on the Saturday she said she wanted to have another threesome. Hosting was near impossible due to the unpredictability of my housemate and she was loving with her friend and her friends bf whilst house stuff with her ex got sorted so we knew we would need to vet a hotel if we were going to do anything like this. We decided to book an airbnb in fact just on the outskirts of Bath, a place I knew well and she had never been so to make a weekend of it...

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By *rishman30Man
22 weeks ago

belfast

Oh good, more!

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By *ricky09Man
22 weeks ago

Gloucester/Cyprus

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By *J GeminiTV/TS
22 weeks ago

Northumberland

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By *urleyboyMan
22 weeks ago

Basingstoke

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By *ndrea54TV/TS
22 weeks ago

cambridge

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By *9Karm69Man
22 weeks ago

plymouth/chesterfield

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By *ark_sentinelCouple
22 weeks ago

Andover

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

On the drive down we talked about what we both wanted to do/ try and ended up with quite a list. Katie set up two tinder profiles on each of out phones showing us as a fwb orally bi couple with some lets say risqué photos on our profile to indicate our intentions. She activated them once we were about 15 mins from the city centre and we straight away parked up in town and headed to the trusty Ann summers. Bought a few things for each of us and headed to a couple of other clothes shops mainly for me to get some new bits for the long weekend. As we went round we checked tinder frequently and I don't know why but I was shocked to see how many matches we were getting when we were swiping. We started messaging a few. The intention really was to spend Friday getting ready and trying to find guys for the weekend. We ed out many many many time wasters and now at the air bnb we went into full overload and we were both messaging several men and a couple of girls each. The excitement may have got the better of us a bit and we had some fun in our home for the weekend but got straight back on tinder. A couple were keen to meet Friday night and as much as we were tempted we wanted to bide our time a bit and we eventually settled on 2 guys we would ask to join us on the Saturday lunchtime and then we would try to arrange something for the evening...

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By *ark_sentinelCouple
22 weeks ago

Andover

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By *ark_sentinelCouple
22 weeks ago

Andover

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By *ndrea54TV/TS
22 weeks ago

cambridge

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By *idLTMan
22 weeks ago

Leeds

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By *onnoisseur100Man
22 weeks ago

Woking-ish

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By *ini1275Man
22 weeks ago

stoke on trent

Living this

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By *umblebiMan
22 weeks ago

ayles

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By *oppy12Man
22 weeks ago

Swindon

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

Glad you're all loving my recollection! It was an amazing time and first time I've really shared it with anyone. If you do have any specific questions, feel free to ask here or privately x

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

So we had 2 guys who knew each other planned to come at half 12. We were still on tinder messaging a few people and were planning what our evening would look like. We had actually considering hosting a bit of a party buy realised it may be a bit male heavy so opted not to do that. Anyway time crept up on us a bit and we realised it was time to get ready. We decided to save matching outfits we had got from Ann summers for the evening or Sunday and Katie opted for a gorgeous black corset, thong and hold ups with above the knee boots with a black skater dress on top and I went for a red/black Bodysuit, a red leather skirt and black blouse and my trusty red patent heels. We didn't have to wait long until a message on tinder revealed they were here...not that we needed the message as we had seen the car pull up. We said to come in and straight up the stairs where we would be in the huge bedroom with almost wall long mirror waiting for them...

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By *J GeminiTV/TS
22 weeks ago

Northumberland

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By *ark_sentinelCouple
22 weeks ago

Andover

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By *hastity_roseTV/TS
22 weeks ago

Nowhere

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By *oppy12Man
22 weeks ago

Swindon

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By *orthampton jamesMan
22 weeks ago

Northampton

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By *un biguyMan
22 weeks ago

belfast

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By *teve1867Man
22 weeks ago

wirral

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By *elly61TV/TS
22 weeks ago

Burnham on Sea

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By *cotty909Man
22 weeks ago

tranent

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

Katie and I had discussed before they arrived some things we wanted to try out and also what we didn't want to do (penetrative was off the cards and had already been made clear with them). When they came up we were sat on the bed and we talked through a few things we wanted to try... the top ones being for us to both be sucking each of them whilst Katie and I fucked (in a couple of different positions), me to suck both whilst Katie sucked/rode me, Katie to suck both whilst I went down on her/ fucked her. They both nodded and agreed. Katie and i started to kiss in front of them and we slid off the bed and on to our knees in front of them. No deliberateness of who ended up with who other than just thats the way round the guys were. We undone their shorts, and pulled down the boxers. My guy was already pretty hard whereas Katie's was about half way. We kissed and started to wank the two guys and then started to turn to them and started to lick and suck them. We sucked and swapped for a decent while and then katie asked if they minded if she got fucked by me now. She got into foggy position and I went behind. The wall length mirror capturing it all with the two guys stood in front of her. She alternated between sucking both in first doggy then reverse cowgirl and a bit of oral on her too. We went into missionary and now was the time to tick off our number 1 desire from the night. Both sucking cock whilst fucking. They squeezed next to each other and rather awkwardly we started sucking each of them next to each other but we soon found a rhythm and a position. It required the guys to take a bit more control which did result in some light face fucking but it was mindblowingly hot. Now was my turn to suck 2 cocks at once whilst Katie rode me. Having 2 cocks in my mouth whilst she bounced on Mr was almost too much. After a few mins I asked her to suck me. I sat on the edge of the bed, her on a knees between my legs and the two guys stood over me. My stocking clad legs spread, still remarkably in my blouse and skirt too I gave the most enthusiastic blowjobs I had probably ever given, then the first guy exploded, a little in my mouth but more on my face. I cleaned him up and focused on the 2nd guy now hungry for more. It wasn't long until he exploded in a very similar vein. More in my mouth this time but equally plenty on my face and almost in unison with this katie gave me a nice hard stroke and suck and I too exploded for her to swallow whole. They seemed very satisfied, said thank you, got dressed and left. Katie and I collapsed a bit on the bed and with dry cum still on me we just laid there and kissed for a good 10 mins. That was by far the hottest experience either of us had ever had and we knee that it wouldn't even be the last of our weekend away... far from it!

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By *rishman30Man
22 weeks ago

belfast

Awesome xx

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By *ark_sentinelCouple
22 weeks ago

Andover

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By *J GeminiTV/TS
22 weeks ago

Northumberland

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By *ndrea54TV/TS
22 weeks ago

cambridge

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By *hastity_roseTV/TS
22 weeks ago

Nowhere

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By *aughtyman45Man
22 weeks ago

lincoln

Very hot !!

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By *orthampton jamesMan
22 weeks ago

Northampton

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By *oppy12Man
22 weeks ago

Swindon

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By *teve1867Man
22 weeks ago

wirral

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By *j and c 2Couple
22 weeks ago

mullingar

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By *aughtyNikki100TV/TS
22 weeks ago

Doncaster

Sounds wonderful x

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By *urleyboyMan
22 weeks ago

Basingstoke

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By *it5373Man
22 weeks ago

here&there

Such a sexy tale xxx

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

So after collecting our thoughts and cleaning up after an incredible couple of hours we got some food and started talking about the evening. Now there were two clear options that we wanted to to do... a mff and essentially a joint bukkake. We had chats going with a couple of girls and one in particular was a South Asian girl who was in her final year at uni. I had never been with a South Asian but certainly had a soft (or hard) spot for them and Katie knew this. We put a bit more effort into her chat than anyone else's but we weren't 100% sure on the authenticity. When we asked for a verification pic things went a bit quiet so we reverted back to option B. We were continuing to message a lot of guys. A lot less picky before we had guys from 18 up to around 50 that we were messaging. Admittedly a lot were clearly only interested in Katie so we filtered out some quite quickly but we started inviting people to come between 7 and 9. We probably stopped this at around 5 so we could grab a snack, shower again and get ready. Between us we counted 22 invites, all with the offer of me and Katie giving them oral pleasure. We knew some wouldn't come as is normal with this kind of thing and we probably expected between 2 and 5 to arrive throughout the time. Anyway, we got ready and this was definitely the time to wear our matching outfits. A full wetlook/pvc look. Bodysuit, holdups, long gloves and heels. Mine all black with my trusty red patent heels, Katie in all red with her black patent heels. But the outfit wasn't complete. I had dabble in butt play a bit with toys and Katie had done a bit with her ex (rimming and fingering) but we had actually never done anything together but on our trip to Ann summers at the start of the weekend we had both bough matching crystal butt plugs. We lubed them up and helped each other put them in just before 7. In true impatient fashion we weren't great at waiting and started having our own fun when mid going down on katie the first knock on the door occurred...

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By *umalotagainMan
22 weeks ago

a town called malice

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By *j and c 2Couple
22 weeks ago

mullingar

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By *exymarvelMan
22 weeks ago

cardiff

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By *oppy12Man
22 weeks ago

Swindon

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By *pforfun1899Man
22 weeks ago

harlow

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

We answer it together and there stands a middle aged guy. Decent looking and his eyes are locked on both of us. We give him a quick intro and invite him in and straight away we both start working on him on our knees in the living room, window curtains wide open for any other guys who turn up to see what they are getting into. Another knock and Katie goes alone this time whilst I continue to go down on the guy and before long we have 5 guys all stood in a row as we swap. One of the guys asks if he can cum and both Katie and I kneel in front of him as he is the first to cum. He decides to leave straight away and is instantly followed by a 2nd guy. Down to 3 guys we think 5 is the max we're getting which is what we kind of expected and we're very happy with that. But the next 10/15 mins are crazy. Within that spell 6 more turn up. In that time I've swallowed a load and he has since left so 11 arrived, 8 remain. Katie and I swap eagerly between them each eventually unable to take any more. A couple leave but a couple who cum decide to stay and watch. One more arrives taking our total to 12. My jaw is starting to ache a bit but I'm so turned on I don't even care and the occasional glance to Katie just encourages us to keep going. In matching outfits and with sprinklings of cum and saliva all over us we know we are oral sluts and all these cocks need sucking. We refuse to stop until every guy is satisfied and finish with 2 guys stood next to each other, us now sat on our asses, backs to the sodas getting face fucked. Now I've been face fucked before this and I'm not the best at taking it but I'm ok but this was the hardest and deepest face fucking I had ever got. They were guys in mid 30s I'd say who later on we found out knew each other and they swapped a couple of times between each other. Eventually both Katie and i got what we had needed, a throat load of cum. 2 other guys had stayed to watch and having seen what just happened were wanking and hard again so of course Katie told them to cum on us whilst I was barely recovering from what just happened. Another facial each and I had never felt so used and so slutty. Katie was undeniably more energetic than I was and asked if I wanted to fuck her in front of the 4 remaining guys. I was fortunately rock hard still. I may have been tiring but you don't turn katie down when she's in that mood so we put on a little show for them in a few positions until the inevitable happened and I couldn't hold it anymore...

The 4 guys abruptly left with me and Katie a bit of a mess. She jumped in the shower and I joined her for a bit. When I got out she quickly told me the girl we had asked for a verification had in fact not ghosted and had sent exactly what we'd asked for...

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By *umalotagainMan
22 weeks ago

a town called malice

Hard reading this x

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By *oppy12Man
22 weeks ago

Swindon

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By *J GeminiTV/TS
22 weeks ago

Northumberland

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By *eelslover300 OP   TV/TS
22 weeks ago

flitwick

Time wasn't on our side with check out at 11am in the morning so we replied to her and to our surprise she was still up. Katie messaged her back and forth and she agreed to get to our place early in the morning about 8am! Turns out she had only had one sexual partner before (an ex bf) and had never been with a girl so was keen to try that but was also into watching crossdresser porn. She had been quite unsure about meeting but had plucked up the courage to. We set our alarm early and got ready. I put on a red dress over some lingerie and my red heels. Katie went for her red wetlook Bodysuit but this time with the boots. Pretty much on the dot at 8am our lovely lady friend arrived. Katie answered the door and they went through to the bedroom together. Katie came back our to say "sabiha" was getting ready. They had spoken about what sabiha wanted/ was willing to do. A few minutes later she stepped out. Oh my. She had quickly snuck in wearing jeans and a jumper but she walked out in a gorgeous lace set and black suede heels. She was noticeably shy and Katie tried putting her at ease by kissing her, then me and then I and sabiha started kissing. As we kissed katie got to her knees and lifted my dress. Of course I was already hard from seeing and kissing sabiha. Katie grabbed sabihas hand and directed her to me. It wasn't long until sabiha was on her knees with Katie and they were both sharing my cock. Normally I was the one on my knees with Katie but definitely wasn't complaining about this switch up. Katie asked sabiha if she wanted Katie and I to go down on her and she eagerly said yes. After making her cum me and Katie started fucking whilst sabiha watched. She started to get involved, mostly kissing and touching me but also touching Katie. With Katie riding me sabiha asked about having sex with me. Obviously we had said no penetrative and we didn't have condoms but sabiha was probably the hottest woman I'd seen with my bare eyes and Katie was probably as keen as I was for her to try me. We agreed that it was what we all wanted and she laid on the bed and I slowly got on top of her and slowly entered her. Luckily she was dripping wet as she was tight as anything. Katie later found out she had only had sex with her ex twice and he was lets say not very blessed in that department. She soon warmed up to me inside her and we alternated between various positions until Katie ruined it saying it was quarter to 11. Sabiha admitted she was feeling a bit sore anyway so I asked where she wanted me to finish. She admitted to never tasting cum so with her sucking and Katie wanking me a bit I soon finished in her mouth. She swallowed and I remember so well her on our knees looking up at me and just saying "I wish every Sunday started like this, thank you". We had to swiftly pack our stuff, sabiha got changed and put her bits in a bag and we actually dropped her off at the end of her road. We never heard from her again but she certainly left a lasting impression on me!

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By *oppy12Man
22 weeks ago

Swindon

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By *ndrea54TV/TS
22 weeks ago

cambridge

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By *ark_sentinelCouple
22 weeks ago

Andover

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By *umalotagainMan
22 weeks ago

a town called malice

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