The Surprise Package

A little about me, I am quite introverted and despite now being in my mid-50s, have never settled down to the traditional marriage with the proverbial 2.4 children etc.
As a result, I've ended up watching more and more porn of all genres over the years: Boy-girl, Girl-girl and also strayed onto 'gay'. I guessed as a consequence of the lesbian movies. This was despite my heterosexual orientation.
I am well aware of the dangers of opening emails from people you don't know but I was feeling pretty daring one evening and thought it would be fun to open a message I noticed from a woman who wrote in a familiar tone.
I had never heard of her but clicked on a link which led to a dating site 'horny meetings' or something like that. After answering some preliminary questions, I proceeded to register and immediately received several messages.
That's strange, I thought. When I clicked on each one, the subject was pretty similar, so I didn't respond.
I returned to my emails and noticed a number of emails had popped up in two categories. Some notifying me of interest on the site I'd just joined and others leading me to similar dating sites.
I didn't join any other sites nor respond to any messages at that time. However, I did continue to read the messages and looked at the pictures, enjoying the attention.
A few weeks later after I'd begun to respond to messages to no avail, I'd been watching porn and was becoming aroused by lesbian and femdom movies, including usage of dildos and strap-on cocks, pegging and cuckold and ultimately gay.
When I paused to check emails, I noticed many notifications from 'Horny meetings' dating site members and as I'd become accustomed clicked on each to read and look at the photos.
Amongst these, I came across one with pictures of a woman in sexy lingerie.
The message was standard and I replied, not expecting a quick reply, or at all as was usually the case but was surprised when a response arrived within 5 minutes.
We exchanged a few messages and I discovered it was actually a cross dresser, not a woman and his name was Charlie Gilbert from Carlisle.
Another couple of days passed and I'd given my personal email address to him by this time as a way of avoiding charges levied by the dating site. A message arrived saying he was coming down to London tomorrow and would be staying at the Travelodge near Liverpool Street. If I wanted to I could meet him at 6pm for a drink in the bar.
I didn't reply for definite as I was still wary but as it was a public spot, went anyway.
There weren't many people in the bar which was quite dimly lit when I arrived just before 6 and didn't see him so sat down. A plain looking brunette in a short dress displaying shapely legs came and sat next to me almost immediately.
I smiled, and she started flirting with me introducing herself as Babs so I offered her a white wine but stated that I was waiting for a friend to join me.
We got chatting and I Etlik Escort kept looking at my watch and looking around whilst enjoying the company of this pleasant lady.
At 6:10, the thought that Charlie had changed his mind crossed my mind at which point Babs revealed herself as none other than Charlie or Charles to be precise.
I couldn't believe it but we continued to talk and had another couple of drinks and a club sandwich with chips to snack on.
I wasn't used to wine and it got me quite tipsy quickly, letting my guard down, and confessing too much so when I was invited to go to his room, I agreed.
In his room, he said that he liked giving and taking oral but hadn't had sex as a woman.
I was getting more drunk and surprised myself by saying that I'd only tasted my own cum. "I haven't been fucked either despite watching gay porn" I admitted.
He laughed and put his hand on mine as we sat on his bed, alarming me. He then put a hand on my groin causing me to gasp and with the other; He took my hand, guiding it under his dress and onto his penis, which was quite hard.
I was hesitant but didn't object when he slipped his growing cock out of his knickers and stroked it using my hand.
"I want to fuck you, do you want to fuck me?" he asked daringly.
"No, I don't want to fuck you." I replied. Thinking I should go now but didn't when he removed his hands, leaving my hand on his cock.
"Let's play a game. to ease the tension" he suggested.
"OK, what sort of game?" I asked.
"We both take our underwear off and show what we've got then the one with the smallest cock sucks the other off.
I agreed, thinking that he must want to blow me seeing as he was in the dress.
When we stripped, his cock was a good 6 inches and my penis about half that.
"I think I'm winning, let's see if we can get your chipolata to grow" He said cruelly, laughing.
After stimulating me for a while to little avail, his became fully erect, growing to well over 7 inches and also thicker whilst mine remained at barely 4 inches
"Let me try something else to give you a last chance before you concede defeat I'll put it in my mouth and see if ee can revive it" he said.
Nothing much happened. "I think yours is in a coma and a lost cause. I claim the win and just as well you don't want to fuck me, I don't think you could penetrate me with your willy." He joked.
"I'm sorry," I replied.
He went to the bathroom removed all his clothes and came back, fully naked.
"Here, get in the part and put these on." He said, handing me his clothes.
I looked at his face closely for the first time and saw he was older than me, probably close to 65 hesitating.
Either you pay for my room tab and my travel expenses or you do as I say. It's your choice." He said.
Reluctantly, I put the clothes on, including the knickers, stockings and bra, whilst Charles leant back on the bed with a glass of Etlik Escort Bayan wine in his hand fully naked.
I sipped my wine and sat on the edge of the bed. He sidled next to me smiled and said. "Don't you look pretty?"
As he leaned in for a kiss, I turned my face away making him a little angry.
He put his hand below the skirt and up my thigh. "Still nothing happening there, are you going to forfeit and pay back my £400 or are you ready?" He asked as he sat their naked.
"I can't give you that sort of money. I'll do it." I replied, looking at his cock.
"That's good, I want some fun." He laughed putting his hand on the top of my back.
He applied a little downward force, to my upper back towards his cock, causing me to exhale deeply, eliciting another laugh.
"Go on, you said you like the taste, you know you want to." He said exerting ever more pressure.
I moved my head closer and he removed his hand. It was now just me willingly leaning forward until my mouth touchec his cock. "Kiss it, lick it." He urged.
I did just that, then opened my mouth and took his cock inside, at which point, he took a photo using his mobile phone.
Undeterred, I continued to lick, suck and bob up and down on his shaft as he continued to point his phone at me.
I got to my knees, grabbed his knees and went to town, now repeating what I'd seen on gay porn movies.
I lapped it up, gorging on his cock.
"Look up., I want to record this moment" Charlie instructed.
I did as commanded, demonstrating my submission to Charlie who began to breathe longer and harder as I continued.
"That's it, suck my cock, relish it, taste my pre-cum, you like that don't you." He said.
I nodded, 'mmm" I managed, still looking into the older man's eyes.
My saliva blended with his pre-cum, which tasted similar to mine. I moaned as I lost my inhibitions as I heard Charles urging me on. "Go on, you're doing great, mm, ooh, aah, oh yes, that's it."
He grabbed my head and held it still with his cock right down my throat, making me gag, and then released me. I withdrew and coughed but resumed when I settled until, I felt a change and realised what was about to happen but didn't stop.
"I'm cumming" He screamed.
Moments later, he filled my mouth but I didn't swallow.
"Let me see, open your mouth," He said raising his phone again. "That's nice, now swallow."
I complied, feeling it slide down my throat and into my stomach, tasting the acrid white fluid.
"That was good wasn't it?' He asked, as he tapped the bed next to him.
I just nodded and sat up. Charles nuzzled my neck and sucked as he groped my man boobs. I was going to have 'hickies' like a teenager tomorrow, I thought. I turned away as I really didn't fancy him and didn't want him to kiss me intimately.
He turned his attention to my legs, stroking up from the knee up the outer and inner thigh, causing my heart rate Escort Etlik to increase. "Take the knickers and stockings off." Charles ordered.
Without a thought, I did it. We now faced each other as he'd stood also, eyes almost level as he was of a similar height, perhaps an inch or two shorter at 5'8" maybe.
Without notice, he brazenly said. "I'm going to fuck you now."
He pulled out some baby oil pushed me down head first and smothered my crack, paying particular attention to the hole, which resulted in a pleasant tickly feeling.
Prising me butt cheeks apart, he aimed his cock in between teasinge and coating his cock before settling at the hole. He pushed in an inch and then a second, causing my sphincter to stretch and giving me a burning sensation. Another inch, as I'd adjusted then. "Here it comes." He warned as he plunged all the way into the hilt.
"Aah!" I cried as I felt the stinging pain of being impaled by Charles' tool.
Holding his position inside me and rocking, he allowed me to adjust and whispered gentlyiny ear. "Be patient and I'll start to screw you very soon. Let me know when you're ready and tell me."
"I'm ready now, please do it". I asked.
"Do what? tell me and beg me for it." He goaded.
"Fuck me, please fuck me. I'm ready, just stick it and have your way with me." I blurted out immediately.
Without hesitation, he pulled back slowly leaving the tip at the entrance, then thrust all the way in. Again and again he repeated this. He'd fully opened me out.
I felt so exhilarated that I moaned and felt my mouth fell open in a smile. "Fuck me Charles. Fuck me hard. I want you to drill me with your big cock, I want to feel every inch smash into me as you take my virgin man pussy. I've never felt so fulfilled" I urged.
That was all the motivation he needed as he really began a hard steady rhythm.
I began to push back, meeting his thrusts as he continued to drive in and out, grunting and moaning in the process.
"Oh yes. That feels so good now, keep going. Fuck me hard." I said.
Charles didn't disappoint. He continued, increasing my pleasure. "Yes, that's it, I'm having an orgasm, fuck me." I was now shouting and anyone passing the room would have heard.
"I'm coming now, get ready to take my cum." He warned.
Both of us were now in full flow "Oh my dirty ass feels so good. Cum in me, I want you to fill me." I shouted.
At that point, Charles took control managing his rhythm before he unleashed his spunk into me.
After we both rested. I had an odd feeling but just smiled when Charles said. "This trip was totally worth it."
I looked down and saw the smeared pink on his cock. I leant over, licked and sucked his cock dry of sperm and traces of my sphincter blood.
I was just getting ready to eave, grabbing my clothes when Charles said. "Keep the clothes, they're not my best and I think you may make use them again you cock slut." Charles said.
I dressed regardless, wearing the knickers and tights over my own clothes. I also put the women's clothes in a bag and walked out of the room and hotel into the cool air.
That didn't go to plan, I thought, still feeling the sting in my ass and cum squishing as I walked to the underground.