Being Caught and Loving It

Hi, I would like to take the time to tell you all about how I lost my oral virginity last Christmas and possibly had one of the best nights of my life.

Christmas was approaching which is my favourite time of year. I love to party but always get jealous of the girls this time of year as they seem to have all the fun, getting all dolled up and wearing cute little party dresses.

Firstly, I think I should tell you a little bit about myself. My name is Geraldine and from an early age have become excited and aroused by dressing in feminine clothing, especially lingerie. I am in my mid-twenties and have a slim physique, although I have managed to get some curves from running regularly and doing lots of squats and lunges.

I also recently moved out of my home into a shared house. It was nothing too flashy but I had my own room with a lock on the door, although there were still communal areas for washing and cooking. Being in my own place with more privacy also gave me more time to be Geraldine which I loved. Also, with the Christmas party season approaching I had ordered myself a red sequined mini dress with adorable little straps, as well as a sexy black satin bra and panty set, with little bows and hearts printed onto the material and matching suspender belt.

The day the packages came I got super excited about trying them on later, and it was all I could think about whilst working that day. I work from home and as soon as my day was over I laid the items on my bed and ran myself a deep hot bath. I also took this an opportunity to shave my legs and body hair, as I wanted to look as feminine as I could later.

I've spent a lot of time in Cross-dressing chatrooms, and have always been amazed about how many guys get off by chatting with a slutty little girl like me. Tonight whilst laying in the bath I was chatting with a guy called Mark over messenger, and I was telling him about my purchases and how sexy they would make me feel, and that the only thing that could maybe make me feel even more feminine, would be maybe wrapping by slutty little lips around a throbbing cock. Yes I know I am a bit of a tease and at this stage, I had never mustered up the courage or had the opportunity to give a guy a blowjob, although the fantasy always seemed to manifest itself when I was dressed or planning of dressing. Mark told me that he was getting turned on and that he was stroking his cock, imagining my slutty little mouth bobbing up on his cock and he even sent me a dick pic of his erect cock. I replied oh my is that slutty little me having that effect on you, and felt empowered that I had been able to turn him on so much. Another dic pic followed shortly afterward, and he had ejaculated from stroking his cock and help from my slutty little comments. I thanked him for the pic and said I had to go and got out of the bath feeling especially naughty.

I normally work from home in my room, but this week as there had been some building work in the room next to mine in the adjacent house I had set up my laptop and headset in the kitchen, which was two floors below and a lot quieter. I also left my old phone downstairs which I primarily only use for Zoom meetings. However, this phone was also linked to the same messenger as my normal phone and unbeknown to me every message of my interaction with Mark had also come up on that device as well.

After my bath, I went down to the kitchen, as I had left a bottle of rum there and was looking forward to getting a little bit drunk as I got myself all dolled up and went back to the chatrooms. As I walked into the kitchen I found my landlord Sean there, and he gave me a bit of a funny look and gestured towards my other phone and asked if that was mine. I said yeah that is my spare phone and it's just connected to the WiFi for Zoom calls for work. Sean explained that he had come round as there was a problem with the washing machine, which he had fixed and that whilst he was drinking a cup of tea at the table messages had kept flashing up, and that he had read some of them.

I had been caught red-handed and started to get really embarrassed that somebody I knew had discovered my secret and knew about some of my naughtiest fantasies. I didn't know what to say and just asked Sean not to tell anybody, because I didn't want people to know about my secret. Sean said fine and that it was none of his business what I got up to anyway as long as I paid the rent, and even apologised for reading the messages. I thanked him and said that would be kind of him.

Sean then said you did seem to enjoy chatting to that guy, and that outfit you were describing do you own it. I suddenly realised that Sean was turned on as well, so I told him that I did and that it had arrived today. Sean then said do you realise everybody else who lived here has gone home for the holidays, and that he would like to see me in it if I didn't mind.

Sean is probably in his mid-forties but is quite tall and good-looking. Oh you would I replied and gave him a bit of a naughty smile, and said OK and said that I would go and get ready. I returned to my room and took off the jogging bottoms and t-shirt I was wearing, and then took the bra off the bed fastened the clip together at the front of my body and then slipped it around so that my breast entered the cups. I then slid the panties up my legs and proceeded to put on the suspender belt, roll the black seamed lace top stockings up my legs and attach them to the suspender straps. I took a moment to make sure the seams were straight and also took a glimpse of myself in my full-length mirror. and was pleased with how good they made my arse look.

It was then time to do my make-up and I started to apply foundation to my face. I have watched loads of make-up tutorials on YouTube, and have become good at doing eye shadow and eyeliner which I applied next. I then started to do some more contouring to make my face look thinner, as well as some bright red lipstick. I then proceeded to put my shoulder-length blonde wig in place, as well as my party dress which barely covered my stocking tops. I finished the look with some black court shoes and then had a long look at myself again in my full-length mirror pleased with how pretty I looked.

I had butterflies in my stomach as I went downstairs to where Sean was waiting. I opened the door entered the kitchen and gave him a little twirl, and as I did I could feel my dress rise exposing my stocking tops for a second. Sean just said wow which just made me feel girly and happy. Then Sean said that I looked amazing, but that he would love to see me just in my lingerie.

I was starting to get turned on by the way this was going, so duly obliged by taking off my dress and letting it drop to the floor and stood there in front of Sean just in my lingerie. Sean certainly seemed to like this and gave me an approving look, and I could even see a small bulge start to appear in his jeans. I then said to Sean seeing as you have seen me like this and been so kind, would you like me to give him a blowjob to which he replied oh yeah.

I took a cushion and put it on the floor in front of where Sean was sitting, and got on my knees and started to stroke his cock through the material of his jeans. I then unbuttoned his flies and reached in to release his cock, which was now only a few inches from my mouth. Sean wasn't fully erect yet, but as soon as I leaned forward and wrapped my lips around the head, I felt his cock start to lengthen as he became fully erect in my mouth.

I then started to lean over even further and bob my head up and down, and as I did I could feel the suspender straps dig into my arse. Here I was on my knees completely dolled up in possibly the sexiest lingerie set I had ever worn, giving my first-ever blowjob. I was in heaven and had never felt sexier or more womanly in my life.

I continued to bob my head up and down, occasionally stopping to just concentrate on the head, and tease his foreskin with my tongue keeping eye contact throughout. Sean started to moan and say how pretty I looked with my mouth wrapped around his cock. But this only encouraged me and turned me on even more, so I started to suck even harder.

Shortly after this, I heard Sean say that he was close and that he was about to cum. With this I started to solely concentrate on the head, running my tongue around in a circular motion and even putting my tongue under his foreskin. This was too much for Sean, and I felt his cock start to throb and was soon rewarded as stream after stream of cum flooded into my mouth. I held it in my mouth for a second, before swallowing and then opened my mouth to show Sean and giggled, before cleaning the rest of his cock with my tongue.

Sean thanked me and left shortly after that, leaving me happy and excited about how the evening had gone.

A few days after this I arrived home to find a package leaning against my door. I took the package into my room to open it and found a pink satin bra, panties and suspender belt, as well as a French Maids outfit.

Who could this be from I thought and giggled.

Geraldine xxx