Written by John D

Cross Dressing
19 Aug 2020


Hi I am a straight male who is in a happy relationship I do watch a lot of porn on my phone lately the usual stuff wasn't doing much for me. I started to look up cross dressers and femboy some of these vids are insanely hot. I have looked at gay porn but when I look at a man I don't feel anything sexual however this femboy/ CD stuff has me so horny.

I jokingly mentioned it to my mate telling him this stuff is hot to watch.

He was pulling my leg saying next time I call to their house he would wear some of his girlfriend s lingerie that she had some sexy stuff.

That was about a month ago and tbh I was busy in work lately and forgot all about our chat. Our partners were going on a night out with friends and I was at home watching football when he text me saying he had picked up some drink and to come over and we'd order a takeaway.

I thought nothing of it had a quick shower while waiting on a taxi and headed over.

When I got there I paid taxi and he headed off I knocked at door and waited. There was no answer so knocked again I heard a voice shouting give me 2 mins from upstairs window.

Few mins later he buzzed me in I headed up to his apartment and knocked.

He answered door in heels lingerie wig and makeup I was gobsmacked looking at him. He said come in babe what you think of my underwear at this point I had butterflies and a hard on looking at him he was clean shaven with lippy on and tbh looked bloody sexy.

As I spoke my voice trembled with nerves not knowing where this would end up I did manage to blurt out you look hot especially in Laura's stockings suspender panties and bra and her lipstick.

He stepped closer and said apparently this lipstick is strawberry scented what do you think at that moment we locked lips.

The kiss lasted maybe 10 seconds before we broke it to reassess the situation.

I looked at him up and down and he looked sexy as hell my cock was throbbing I couldn't help but pull him in to me and kiss him again while groping his tight ass in her panties I ran my fingers through the strap of the suspender belt and along the top of his stockings this was my fantasy I'd wanted with weeks now.

At this stage he was French kissing me hard the lust was so strong for both of us he reached down my pants and started jerking me off I had never been so turned on I reached down and released his cock from the panties and started returning the favour.

This was pure lust we both wanted it so bad we couldn't didn't want to stop.

If we thought this out we might not have went through with it so I wasn't stopping his ass was gonna be mine tonight.

He stopped kissing and told me he had snuck a peek at my cock a few times in the gym shower and always wanted to taste it I wasn't gonna stop him. As he took me in his mouth it was sooo good every now and again he would break the bj to explain Laura knew he liked dressing up in her underwear and she had read somewhere that some men were into it.

She didn't mind and was open to him wanting to be pegged by her the odd time he explained he wasn't gay loved fucking her pussy but did have a kinky side to his bisexuality.

They were into the cuckold lifestyle and had met a few men who fucked them both online Laura was hornier than I thought obviously and Jeff was lucky that she was into this stuff too. Her only rule was nobody they knew was to find out he is telling me this as he is sucking his best mates cock and her cousins boyfriend so the cat is out the bag now to me anyway. Straight away my mind shot to I want to fuck them both now as I had often relieved myself thinking about Laura when my girlfriend Gemma was out.

I was getting close to cumming as he gives good head so I put my hand under his chin tilted his head up to me and kissed him again my mind telling me don't cum too quick without the main event. I kissed Jeff and told him this might never happen again so I want to fuck him before I cum he said Laura had told him they were not to be home until 4am at least that gave us nearly 8 hours to get this fantasy fulfilled.

Breaking the kiss again he told me he wanted me to fuck and cum in his mouth that he had dreamed of tasting my c ock and had tried to persuade Laura to let me fuck both of them but she refused because it was too close to home. He kissed me again and said give me your load and I'll do my best to let you fuck me and Laura I know you fancy her too, he was right so I said to him on one condition do I cum now I want a pair of Laura's panties so I can fantasise about fucking her and you at the same time while sniffing her panties, Jeff smiled and went to laundry basket picked out the black panties Laura wore earlier they were Ann summers panties very sexy and had a beautiful musky scent and little stain where her pussy had been all day my cock got extra hard and I kiss him while putting Laura's panties in my pocket as we break the kiss I nudge him down to take me in his mouth and finish me off this was Gonna blow my mind I looked down at him in his blonde wig and lipstick and could see his stocking clad legs too I took out Laura's panties had a, sniff and blew so hard in his mouth it felt like I came for ages I had so much cum, he took it all in his mouth but I came so much it spilled out down his chest and made its way onto her bra this was soo hot I pulled him up to me and kissed him while we swapped my cum we halved the load and he swallowed I went behind him asked him to bend over and dropped my cum on his bum from my mouth.

He was purring with satisfaction as I popped my thumb up his ass to push the cum in he asked me to go into bedroom and told me where to find her buttplug bring it back and popped it in his ass to keep my cum in him.

He kissed me cleaned my cock then kissed me again. Let's get cleaned up order some food and later we can fool around again and see can we hatch a plan where you can fuck Laura too over some food.

I feel a bit sick in my tummy with guilt but there's no going back now the whole situation runs through my mind my friend just let me cum in his mouth has promised I can fuck him in his ass in women's his woman's lingerie who has a buttplug up his ass to keep my cum in him and the promise of maybe getting to fuck my crush with years who I now have her panties to sniff while I wank has me too invested to back out now.

Hope ye enjoy

Would anyone like the next chapter

Tags: crossdressing, cuckold


Comments