Hi, my name when I dress is Gabby. I decided it was time to update my photos as I had been on a buying spree, so on Friday night I checked into an Essex hotel with my new outfits, wigs and boots. A few enjoyable hours later I has just over 100 new photos of me dressed as the girl next door, the secretary, classy lady, flight attendant, school girl and the slut. After making sure all my makeup, lipstick and nail vanish had been removed I ventured down to the hotel bar for a drink or two. Despite being 8pm the bar wasn’t that busy so I sat myself on a stool at one end and ordered a pint. After making sure the barman had moved away I took out my phone and started a slideshow of my new photos. I was about half the way through them when another guy sat down two stools up. He nodded to me and I did like so. After about 10 minutes he introduces himself as Adam and we start to chat. The usual chit chat, football, the weather, then Adam tells me he’s from the Midlands and in Essex on business and then he asks me why I’m at the hotel tonight. Decision time do I make up some work related story or tell him what I’ve been up to in my room. I’m never going to see him again so I take a large swig of my drink and tell him that I’m a TV and I’ve been taking photos of myself whilst wearing full makeup, wigs, woman’s clothing, underwear and fuck me boots. Another big swig of my drink. Silence for a couple of minutes then Adam asks what sort of outfits I was wearing. Looking down the bar the barman was busy at the other end so I asked Adam if he wanted to see the photos. He nodded and moved up a stool. I took my phone out and opened the folder. I didn’t put it on slideshow but passed it to Adam and told him to swipe each time he wanted to move on. It took him about 10 minutes to view them all. I noticed that he lingered on the photos of me wearing the red dress, blonde wig and sucking a dildo. He also stopped for longer on the slut outfit photos which featured my almost crotch length boots, black stockings and again a dildo filling my mouth. Adam passed the phone back and then started asking me questions about why I dress and why I’m sucking a dildo in some of the photos. Our drinks are nearly empty so deep breath and I ask him if he wants to see me dressed in one of the outfits. He looks at me for a few seconds and says the outfit at the end looks fun. Typical he’s gone straight for to slut outfit. Time to take charge. I say to him that the slut outfit is not available to him as we have only just met but I would put on the red dress that he had stopped at nearer the beginning of the photos. I stand up tell him my room number and tell him to knock on my door in 30 minutes.
Whatever confidence I had quickly evaporates as I walk back to my room but once safely in my room I recover. What’s the worst that can happen? I dress up and Adam doesn’t knock or he turns up and I let him see me and maybe we have a bit of fun. I quickly take off my clothes and put on matching black bra and knickers with pink edging. Next my silicon insets are put inside the bra to give me a 36B chest, then black suspender tights are rolled over my legs. The red dress is next, it’s thigh length and sleeveless but has a full length front zip which when pulled all the way up covers my chest. Next into the bathroom to put on my makeup. As time is short I just put foundation on my face and neck along with bright red but don’t paint my nails. Back to the bedroom to put on the blonde wig and a necklace and bracelet to complete the look. I look at myself in the mirror and as I have quite a small cock (perhaps that’s why I dress up as a woman) there is no awkward bulge to spoil the look of the outfit. Check the time 28 minutes gone.
After 40 minutes has passed I’m thinking Adam is a no show when there’s a light knock at the door. After checking through the spy hole that it’s him I open the door halfway and step back half a pace. Adam just stands in the corridor not moving. Not wanting to be seen by another guest I take control of the situation, put my hand out take his and pull him into the room. With the door safely shut I usher him into the room. I move pass and stand in the middle of the room. I do a slow turn and ask him what he thinks. He replies very nice. I ask him to call my Gabby when talking to me and then I move towards him. My fingers run down his right arm and then his left arm. I turn my back to him and move backwards so our legs are touching, his crutch is against my arse and my back is against his chest. We stay like that for a few seconds then I reach down and take his hands and bring them to my false tits. Using my fingers I push against his fingers so that he is now playing with my tits. Now there is a definite movement in Adam’s trousers. After about a minute it’s becoming clear that if there is going to be any fun tonight I’m going to have to instigate it. So I turn round and kiss him lightly on the cheek. My left hand starts to rub his chest whilst my right hand starts on his cock through his trousers. No doubt now there is definitely signs of interest from Adam but he still just stands there. It’s now obvious that I’m going to have to do all the work tonight so I quickly unbutton his shirt and remove it. I tell him to take his shoes and socks of which he does then I undo his belt, unbutton his trousers and let down the zip. I go down on my knees and using both hands pull his trousers down and help him out of them. I’m on my knees in a hotel room dressed as a woman with a bloke who is now only wearing a pair of boxers. If I ever want to have a real cock in my mouth as opposed to a dildo this was my chance. I seem to go into autopilot, my hands moving to his hips and then his boxers are moving down his legs and are gone. There in front of my face is his cock and it’s rapidly rising. I move my right hand onto it and slowly start to wank him. After about 30 seconds of this it had grown to about 6 to 7 inches, not too fat but definitely far bigger than mine. I look up at him ask him if he wants Gabby to give him a blowjob. He looks down at me and says yes. I reach into my bag by the wall and pull out a box of flavoured condoms. I select the apple one open it and then put it over the tip of his cock and then roll it down. A this point it occurs to me that I’ve never given a blowjob before so I close my eyes open my mouth and lower it over the head of his cock. My tongue starts to flick around his head and then I take more of him into my mouth which I then close and start to suck his cock. This has the desired effect as I feel his body go stiff and him hands are on my shoulders. After a minute of hard sucking, I come up for air and whilst using my right hand to wank him continue to work on the head with my tongue and mouth. About 5 minutes later I sense he might be reaching coming point so I clamp my mouth over his head really tight and suck extra hard. Almost immediately I’m rewarded by him coming into the condom. He probably shot 3 or 4 decent amounts followed by a couple of smaller amounts. I keep his cock in my mouth for a few more seconds before releasing it. I look up at Adam with a big smile on my face.
I suggest that he goes to the bathroom to clean up and whilst he’s gone I lay myself of the bed awaiting his return. When he comes out of the bathroom I ask him if he wants me to change into something more comfortable and join me on the bed. Much to my annoyance he’s a come and go man. He says no and rapidly dresses and almost runs out of the room. Once he has left I change out of the dress and put on a body stocking with easy front and rear access along with a very short and sexy nightdress. I lay back on the bed replaying in my mind the last 20 minutes. Every now and then I look at the door hoping that Adam will change his mind and come back to join me in bed. After the work I had just done I wanted Adam to take me to bed for a cuddle and a few kisses and I definitely wanted Adam’s cock back in my mouth. Well Adam didn’t come back and next morning I looked for him at breakfast without any luck. So I packed Gabby away and checked out of the hotel.
I hope you have enjoyed my first blowjob. I certainly did and from the amount in the condom Adam did at the time. This has certainly wetted my appetite to do it again and maybe next time my man may be a come and stay and not a come and go.