My First Time With Old Man in Girls Undies

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My First Time With Old Man in Girls Undies
First, me say, this is a true story of how I lost my anal virginity but to protect my privacy and the people in the story, I will be changing people’s names.
This story is set when im s*******n and had just began experimenting with crossdressing and having gay thoughts. My favourite categories on this site are Bisexual, Anal, Shemale Fuck Guy, Guy Fucks Shemale and Latex. I was also broke as fuck and unemployed and summer was just around the corner so I needed money fast. It was around this time I remembered about the casual encounter section of Craigslist. I had been wanting to experiment with guys for a while by this time and the most id done was suck off my gay friend Darren when we were drunk once. It was a Sunday evening and I was horny as fuck so I posted an ad saying something along the lines of “closet xdresser, skint and will do anything for reward” along with my location and stuff with a few pics of me in girls clothes and my dick.
About an hour later I started to get flooded with responses. Guys of all ages and sizes were asking to fuck me, get fucked or just oral and were offering £10-£50, but then one email caught my attention. It was from a guy called Roy, he was 45, lived nearby, wanted a blowjob and for us to fuck each other, he wanted to pick me up and do it in the woods behind our local villages and was offering me £300! I was being offered £300 in cash to lose my anal virginity and to fuck him, my stomach started to do knots but I thought of the pleasure and the cash and replied to Roy and told him to pick me up from a nearby petrol station at 8pm.
Roy asked me to wear girl’s underwear under my guy clothes so not to attract attention when picking me up. This was back in the day were I didn’t buy my own girls clothes and would steal my female friends when I was at their house for a party or something. I wore my friend Kates lacy yellow matching set, they were B cups so not so big it looked silly and the underwear made my already feminine butt look better.
I emailed Roy that I was wearing a black hoody and would be waiting for him at the petrol station and left my house with a pocket of lube and condoms. It was only 8.05 when a red Honda came into the station and stopped alongside me and rolled the window down. Inside was a middle aged man, with grey hair and beer belly. I could tell he was over 45, maybe late 50s but for some reason that just made me hornier. He asked nervously “Are you Amber?” Amber is the name I give my female persona for those of you that don’t know. I replied “yup!” and jumped in the passenger seat.

Not much was said on the drive to the woods since we had emailed the details of everything to each other before meeting so he just drove straight to the entrance. We got out and it was just starting to get dark so we had to use our phone torches on our walk to find a good and hidden spot. After about 10 minutes of looking we found a fallen down tree surrounded by Douglas Firs about a 5 minute walk from the main path so no one would spot us walking past.
I perched our phone against the trees so we didn’t have to hold our phones for light and by the time I turned around he had dropped his trousers. He unzipped my hoody to reveal my bra and started squeezing chest and kissing me roughly with a lot of tongue. I felt his hand on my head and he started to push me down towards his dick. I unzipped him and out plopped a wrinkly 4 inch penis, it was short but dear god it was girthy. He probably hadn’t trimmed his pubes in months and it was surrounded by grey hair
Darren’s was much longer but skinny so this was completely new to me, I could barely fit it around my mouth. It was easy enough to deep throat so I went balls deep and started to rub his giant testicles, the guy probably hadn’t wanked in weeks! I was bobbing my head down on his massive chode for about 20 minutes when I felt him starting to tense up and pre-cum hitting the back of my throat. I took it out my mouth to catch my breath and wanked him furiously until he started spurting jets of cum. One shot hit me right in the eye but I quickly shoved it down my throat and swallowed the rest of his load. This was my first time swallowing too as I passed out from drinking when I sucked off Darren and I could tell it wouldn’t be my last time drinking cum.

I wiped the cum from my eye and licked my fingers clean. He then told me to put a condom on and fuck him. I couldn’t get my trousers off quick enough, I pretty much threw them up a tree I was that horny. The night breeze felt great on the lacy underwear which only helped my raging hard boner. I put on a condom and lathered my dick in lube, Roy was leaning over the fallen down tree with his cheeks spread waiting for me.

Here I was, about to fuck a guy for the very first time and he was so old! I rested my bellend against his asshole and gently pushed. Oh my god it felt so good, he was so tight and so warm. I started off slowly since I didn’t want to hurt him by putting all 7 inches in at once but soon after I was going as fast as I could. I was like a dog in heat! His moaning was what turned me on the most knowing that it was my dick causing that pain and pleasure. After about 20 minutes of fucking I could feel myself about to blow so I clutched at his back hair and started pumping his ass with all my might! To this day I don’t think I’ve came as hard as I did that night, it felt like I was jizzing for 10 minutes! I pulled out and it made the hottest noise I ever heard.

I collapsed on my back absolutely exhausted, I stared up at the skies in absolute ecstasy. Suddenly I felt Roy remove my condom, I looked up and I saw him holding the condom upside down above his mouth, I saw all my semen go straight down his throat, it didn’t even phase him, it was so hot. So hot that I needed some myself, I got up and lunged my tongue down his throat, the taste my own cum wrapping around my tongue, I got hard almost instantly.
I could feel Roys dick getting hard too so I suggested that it was his turn. Without skipping a beat he lifted me up pulled my lacy pants down and bent me over the same tree. I felt his dick rub against my ass, I was so horny and so ready to lose my anal virginity. What I was too caught up in the moment to realise was tht he didn’t put on a condom. I whimpered “What a cond…ahhhhh” he shoved his penis right in me, all the practice id done with hairbrushes and toys had made me pretty loose but god it still stung.
I begged him to stop and put on protection and lube but he promised he was clean, in fact, I was the first guy he had fucked too, knowing id taken an elder man’s anal virginity made me hard again! I started to wank myself off while he fucked my ass, I could not waited to feel what it felt like to be pumped full of cum. I gripped on to the tree as Roy started to get faster, my hole was on fire but I was getting so much pleasure from it I was ripping the bark from the tree.
Roy pulled me off the tree and laid on his back and told me to squat on his dick. I did so and this position was so much better his dick went further up me and I could grind his dick a lot easier. 15 minutes into this and I felt Roy tense up again, I knew it was coming, literally. I started to wank myself furiously and as I came, I felt pump after pump of jizz erupt inside me and let me tell you, it is the best feeling ever.
I collapsed onto Roy, the jizz I got on my stomach rubbed between our chests as we kissed each other passionately for a while until we built up the strength to get up. We eventually got up and put our clothes back on and made our way back to the car. On our way through the woods I kept trying to zip my hoody up but I must have broken the zip by taking it off too quickly. “Fuck” I thought, “all I have underneath is a lacy bra”. I just gripped it shut since it was so cold and I was still pumped of adrenaline…and cum.

We got into the car and Roy opened up his glove box and pulled out a wad of £20 notes, he counted out 15 twenties and passed me them, winking at me and thanked me for the great night. He asked me where I wanted dropped off, my ass was too sore to walk back from the petro station but I didn’t want him knowing where I lived, so I got him to drop me off at a small park in between the two. He kissed me again as I left the car and i’ve not seen or heard from him since.

On my way home I could feel the cum leaking from my asshole. It felt great! I felt like a real slut! I was about 5 minutes away from my house when I saw someone walk towards me, as we got closer to each other I saw that it was Darren, we smiled at each other and I waved. I forgot about my broken zip and when I waved my hoody opened revealing my yellow lace bra. Darren’s face was a picture, I could tell he was confused but he had a massive smirk on his face. I stepped towards me and pulled my hoody off my shoulders and rubbed my chest. He said “I always figured you had a secret, now…why are you out this late by yourself dear?”

Fuck, how was I going to explain this…?

To be continued…

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