Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereI hugged and replied, "No worries; he might be a hunk, but I could still kick his ass."
Dave came over to us and said, "Ready to go?"
"Abso-fucking-lutly." I said, wrapping my arm around his as we left the club.
Outside the club, Dave hailed a cab and I gave the driver my address. As the cab headed to Hanwell, Dave and I made out in the back of the cab. My hand wandered down to his groin, and his hand was gently cupping my left breast.
The cab driver broke us out of our erotic state when he announced that we had arrived at my flat. Dave paid the driver and I took his hand and led him inside.
After I closed the door, it suddenly dawned on me why I brought Dave here. I also felt Dave was hit with a bad case of nerves.
I forced myself to meet his eyes and said, "Well here we are, you still up for this?"
He just nodded like a cute schoolboy's first time with a girl.
I took a deep breath took his hand, and led him into my bedroom. I turned and faced him and our lips met, and the nerves melted away in his embrace. The sexual tension that was building all night finally burst into sensual release and we were both as one as we explored each other's bodies.
He unzipped my dress and it pooled around my feet, as I unbuttoned his shirt. I slid the shirt off his shoulders and to the floor and I placed my hands on his chest. He worked out and I found myself exploring every inch of his manly torso.
As I got to the bottom of his abs, I started to free his belt and open his jeans. I lowered myself to my knees as I slid his jeans down his legs. Now, I was mere centimetres from my first real cock, and only the thin blue boxer shorts were the only barrier between me and my goal for the evening.
I leaned forward and took a sniff of the hidden member, the subject of my recent obsession since I became Brenda. I reached for his waistband and lowered his shorts, and there it was a nice 5" cock completely stiff because of me.
I ran my hand down the shaft and he let out a little moan. I knew what a cock looked like, I had one my whole life, but this was the first time I got up close and personal with another man's penis. It was warm and pulsed with my every stroke.
As if on instinct, I took the head into my mouth. I savored the soft fleshy head as I rolled my tongue around his piss slit. I had my first taste of another man's juices, and it was like a nectar I knew I would crave for the rest of my life.
The blowjob practice I had done with my dildo paid off, as with little effort I had the head of Dave's cock into my throat.
"Oh, fuck!" escaped Dave's lips
I become a woman possessed, as I feasted on his cock.
Without warning, Dave cried, "SHIT, I'm cumming."
His cock head expanded in my mouth as he fired several ropes of semen into my mouth. It tasted far better than my own, and I was disappointed when it stopped spuing jism into my mouth.
His cock dropped out of my mouth, and I swirled his seed around with my tongue, before swallowing his load.
I stood and kissed him on the lips, he did not notice the taste of his seed on my breath as we kissed.
He reached behind me and unhooked my bra. Once my breasts were free, he lowered me onto the bed. Dave climbed on as well, and his lips were on my nipple. The new sensation caused my back to arch, and my own dick was soaking my panties with pre-cum.
Coming up for air, he whispered to me, "Do you have any lube?"
I reached into my nightstand and retrieved the lube, passing it to Dave.
He slid my panties down and off my feet, giving him his first look at my penis. Dave rolled me onto my side and lifted my leg to expose my anal pussy. With some lube on his finger, he gently rubbed around my hole. His mouth was back on my breast as he inserted his digit into me.
I whimpered like a schoolgirl as he hit my prostate. Again, my dildo training was paying off as he soon had three fingers in me, opening me up for the main course. I reached my hand behind me and found his semi-hard cock, and started to stroke it.
I turned to Dave, "Are you going to finger me all night, or are you going to fuck me."
Dave pulled his fingers out of my arse, and I yelped. He pulled me to my knees and pulled my legs apart to allow him access to my rear end. I heard him slather his cock with lube, before presenting the head to my sphincter.
Again, my dildo training kicked in and I took a deep intake of breath, as his head entered me. I had a rush of emotions as I was being deflowered, it had been a short three and half months since I headed down the rabbit hole of becoming Brenda. As Bryan, I could never have imagined I would have knelt on my hands and knees as a strange guy feeds his cock into my arse, but here I was. And what is more, I was loving it.
As Dave's cock grazed past my prostate, I lost my shit. My eyes rolled back in my head, as my own dick leaked like a fireman's hose.
With a grunt, Dave's balls slapped into mine. I pushed my hips back towards his as I wanted more of him in me.
Dave grabbed my hips and pulled his cock most of the way back out before slamming it back into me.
I turned my head to face him pleading, "Fuck me, I need you in me."
With the encouragement he needed, Dave started to thrust in and out of me. The silicon toys were no substitute for the real thing sliding in and out of my arse. My soul was on fire as any last masculine resistance was excised from my being as I embraced every pleasure womanhood had to offer.
Without warning my cockhead swelled, and fired my seed all over the bed, tears of pleasure streaming down my face.
I felt empty as Dave pulled out of me, and then flipped me on my back. He lifted my legs over his shoulders as he re-entered me without resistance. The look of lust in his eyes was for me, I was bringing him as much pleasure as he was me.
His face met mine and our lips and tongues danced as he fucked me. I clamped my eyes shut as another orgasmic wave overcame me and I squirted over Dave's belly. Dave's face stiffened as the pace of his thrust increased. I knew the sign of a man on the verge of climax.
"Cum in me," I panted, "Fill me with your seed."
With a primordial grunt, Dave coated my colon with his issue. Each spasm gave me more of his man juice within me until he gave a final twitch and withdrew himself.
Dave flopped onto the bed next to me breathing like he had run the 100-metre dash.
"Fuck, that was great," he declared, and I had to agree with him.
After he regained his breath, there was an awkward silence. Dave just gave me a sheepish smile as it dawned on him that he just fucked a transexual. Though any masculine feelings had left me, Dave was showing that awkward deminer of someone who wanted to leave as quickly as possible.
I had to laugh having been in his position with girls after I fucked them.
I rested a hand on his shoulder, "It is okay, you can go if you want to."
"I don't want to be that guy that fucks and runs," Dave said conflicted.
"It is Okay, "I reassured him, "I have an early morning anyway."
Freed of any post-sex burden, Dave got out of the bed and dressed, as I got up and slipped on a blue satin nightgown.
"Ah, thanks for a great time," Dave said, and I just smiled back, "It was indeed."
I showed Dave out and headed to the bathroom as my gaping arsehole was starting to expel his spunk.
I checked my phone and I had a text message from Stacy checking I was alright. I message back telling her all was good on my end with a winky face. She replied calling me a slut, and I burst out laughing.
I had a lazy Sunday, and though a little sore in the butt, I soon recovered and knew I wanted more of the action I had the night before.
Monday morning soon was upon me and I was up and dressed in my business skirt suit and headed to the train station to head into the office.
At break time I caught up with Karen, Tara, and Sam about our respective weekends. I blushed when I mentioned that I hooked up with a college kid, and they teased me by calling me a MILF.
So, I settled into the week of trades and boring meetings. Gregg's attitude towards me was souring fast as I was making him look inept in the incoming sales figures.
Friday night, I said my goodbyes to the girls as I headed home. Tonight, I was going to have a bath, get a takeaway delivered, and veg in front of the TV with a bottle of wine.
My planned relaxing evening almost went to plan, shortly after I settled down in front of the TV there was a knock at my front door.
"Who the fuck is that," I said annoyed that my alone time had been disturbed.
I opened the door, and there was a woman, not dissimilar to me standing there.
"Brenda Chaplin?" she asked.
"Yes, can I help you?" I asked, suddenly nervous.
She gave a wry smile, "Funny you should say that because I'm Brenda Chaplin. I believe you are using my identity."
Shit I thought, how can this be, I said to her, "You had better come in then."
I led Brenda to the living room and she took a seat on an armchair, and I sat on the sofa.
"How did you find out?" I asked, not sure I wanted to know the answer.
Brenda gave me a reassuring smile, "I was bumming around from place to place with my boyfriend. I caught him sleeping with a local girl in the village we lived in. So long story short, I dumped his arse and decided to come home."
I took a slug of my wine as I tried to process what she was saying, she continued, "Anyway, I made my way back to the UK, not easy I can tell you without a passport. So, after bumming around the country for a bit, I decided to go and see my old friend Stacy. Well, the blood drained from her face much as it did yours."
I got up and grabbed a second glass and poured her a drink which she accepted, then continued, "Look, am I pissed that you've stolen my identity yes, but after a long chat with Stacy I can kind of understand the position you were in. I am also very impressed with the plan you two came up with, and I have to say you make a pretty convincing woman."
I blushed and said, "Thank you I guess."
She took a sip of her wine, "It looks to me like we have a situation here, but I think we can come up with a solution that benefits all of us."
I placed my glass down and said, "Okay, I'm listening."
"First off, I have no desire to get back into the fucking rat race that drove you to do this, and second, I do not want to stay in the UK any longer than I need to be here. Being back has reminded me why I did not come back after my gap year. So, as I see it, if you want to buy my identity from me, then I'll happily disappear again, and you can get on with your life as me."
"How much?" I blurted out, a little too eager.
"I'm not greedy, just enough to get me wherever I'm going and a little money to get established there," she said.
I thought for a moment, I had a fair bit of money stashed offshore, and I did feel bad about taking her identity. I ran the numbers and said, "How about 50K?"
"Wow," she said, "I was not expecting an offer like that, look I'm not greedy and I don't care about money, so I'll take 30K, and that should set me up nicely."
I was in shock at her counteroffer, and she raised her glass. I raised mine and we clinked them together and I said, "Deal."
Brenda left shortly after we made the deal. I fired up my laptop and started to move the funds around to pay Brenda off. 30K seemed like a lot of money, but at the rate I was earning I would make the money back in less than 6 months. As it would give me peace of mind about my identity being blown it was a low price to pay.
To keep the money transfer separated from my new identity I transferred the funds to Bryan's account in Germany.
After explaining the situation to Stacy, I planned my trip to Germany. The funny thing was I had to now look like a man again in order to withdraw the funds for Brenda.
I hit the internet and ordered a muscle undershirt and a fake stick-on beard. I hoped it would be enough to convince the banker I was Bryan.
On the way home from work one evening, I swung by a male clothes shop and brought myself a new suit, shirt, and tie. When I got home, I poured myself a glass of wine, went to my bedroom, and stripped off my business suit.
Sitting at my vanity table, I removed my makeup before straightening my hair, and tied it back into a ponytail. After taking my bra off, I used some bandages to wrap around my breasts to get them as flat as I could.
I then pulled on the muscle undershirt and my breasts were causing a small rise, but not enough to be noticeable. I pulled on my new male shirt and for a second, I was confused that the buttons were on the opposite side of my girl blouses. I still needed a belt despite the muscle shirt, but the trousers hung well.
Back at my vanity table, I applied the glue and fake beard, and it blended well. Though my face was lighter than before a convincing-looking Bryan was staring back at me in the mirror. I put on my tie and suit jacket. I realised I forgot to get men's shoes, but I found a pair of my flat shoes that would do until I can buy some proper ones.
I took some cash and bank cards out of my purse and slipped them in my pocket with my phone and keys.
After leaving the flat, I took the tube over to Kensington and knocked on Stacy's door.
She opened the door, not recognising me, "Can I help you?"
I burst out laughing, "It is me, Brenda, if I can fool you, I will have no problem with the bank in Germany."
Stacy did a double take as the penny dropped, "Fuck, I see Bryan now. There is a face I thought I'd never see again."
I spent the rest of the evening at her flat drinking wine and watching TV. She was being overly flirtatious with me, and it took all my self-control not to make a move on her.
It was around midnight by the time I got home, and took me another 40 minutes to remove my male disguise and slip on my satin nightgown. Though tired, I was horny after my evening with Stacy, so I reached into my bedside table and removed my favourite toy and a bottle of lube.
Within minutes the toy was deep within my arse, and my cock was leaking like a tap as I fucked myself with the silicon toy inside me. I did not take long before I had to cover the head of my cock as it released its load into my hand.
I licked my issue from my hand savouring the taste, not wasting a drop. I pulled out my toy, wiped it, and stuck it back into the draw.
Now satisfied, I was soon sound asleep.
The following Wednesday, I was standing in terminal 5 at Heathrow waiting to catch my plane to Berlin. I wore a charcoal skirt suit, with a white pussy bow blouse. I oozed the appearance of a successful businesswoman I blended in seamlessly with the other businessmen and women waiting to board the flight.
A few hours later, I was standing in Bryan's flat. There was a stack of mail that was mostly junk mail, but I fired up my laptop and took care of the items I had to sort out. Luckily, I had set all the payments for the flat and utilities on automatic payments to Bryan's account.
As I lay in my bed, I was feeling melancholy at how the last few months my life had taken a 180-degree turn from where I was. As I left this flat to start my journey, I would never have believed if anyone told me that I would come to embrace my new identity to such a degree I would enjoy sex with a man.
The next day, I was up and dressed in my male disguise, and with all my old male IDs I had left at the flat, I headed to the bank.
However, I was nervous as hell as the bank issued me a banker's draft for £30000 made payable to Brenda Chaplin. The bank manager did not question me as my papers were all in order. The irony was that these papers were the genuine ones, and I entered the country on a fake passport.
I had lunch in the city, before heading back to my flat to transform myself back into Brenda. When I was ready and the draft hidden within the business papers in my case, I took a cab to Berlin Brandenburg airport.
I was more nervous going through security with the banker's draft than the fact I was using a fake passport. But all went well, and I enjoyed a gin and tonic whilst sitting in business class on the plane.
I cleared UK border security without fuss and finally relaxed whilst riding in the back of the cab taking me back home.
A few days later I deposited the banker's draft into my Brenda account and contacted the real Brenda to tell her I was ready to pay her. She requested a £2000 cash payment, which she would collect that evening.
When Brenda came to my flat, I handed her the envelope with the cash in it.
"Thanks," she said, "I need this to buy my new identity."
"Wow, I thought fake papers would cost more?" I replied.
She smiled, "It is only £1000 for the new birth certificate, passport, and driving license, the rest is for me to live on till I can get a bank account set up."
"When you have your new name, we can set you up an account overseas and I will transfer your money into that account," I recommended.
"Good plan," She replied.
For the next hour, we sat and talked over a glass of wine. I went over how Stacy came up with this crazy idea to get me back into work. Brenda thought my story was good enough to be an oddball comedy like Tootise,
I asked her about her plans and she said she was going to move to Greece and open a bar. I joked that I'd come to pay her visit.
The next week she was back with her new documents with her new name Helen Wilson.
"I never really cared for the name Brenda anyway," She replied when I commented on the new name.
Helen Wilson was a real person, the same age as the real Brenda, but had died as a baby. Brenda, or as I called her from now on Helen, explained that her guy could hack into the government records and erase the death certificate, but also copied Brenda Chaplin's history onto Helen's so she had all the same qualifications as she had before.
"Helen, that is incredible," I said, astonished at how advanced it was now to get a fake ID.
Helen joked, "You never know if I get bored of running a bar, I might try my luck at Jackson and Wright."
With her new bank account in Greece now set up with a healthy balance of £28000, we hugged, wished each other luck, and said our goodbyes.
She still has to get revenge for Bryan getting shit on. Maybe she falls in love with a police detective, or Army intelligence and they plot together to take down Gregg the perv and the officers who had him fired and only allow the women a certain level of success. Her and Stacy could get back together and live happily ever after.
I really miss this series.. please keep posting. Waiting for next chapter ASAP.. LOOOVE
Id forgotten about this story nice addition
Is that the end?
if so great story
Thanks
xxxx