Before I bare the details of the night that took me back in time, I should tell you a bit about my past, and my present. Before marriage, I used to cross-dress quite often for tops who enjoyed my slutty alter-ego. I enjoyed being the dressed up slut, begging and hogging on cock. I had shoulder-long hair, pretty slim body, and I used to keep it hairless.
Despite all that, in normal life, I looked pretty much like any straight guy. But with the right dresses on, a bit of makeup and lipstick, I would turn into a proper slut. Even if not beautiful like a real girl, femme enough to lusty men to enjoy my body.
But since my marriage, I stopped dressing up or keeping my body feminine. Now I have put on some weight around the waist, even though not fat or chubby. Luckily, most of it has gone on my ass and a bit on my boobs, so it’s an even better treat for tops.
This incident happened a few months ago, in September, quite before the incident of my other story about, “Rooftop Romp with Watchman”. I met this mature guy on a flight while coming back from Bangalore. I had gone to Bangalore for office work and had taken a really early flight in the morning.
The return flight was late in the night and it was delayed by almost an hour. I was tired and I tried to take a small nap while I was on the flight. Unfortunately, the nap lasted for only 20 minutes or so and I woke up due to small turbulence. I opened my eyes and glanced over. The mature guy was sitting next to me and reading something on his mobile.
Unable to sleep again, I just sat looking outside the window. There wasn’t much to see because of the night and dark rain clouds. I peeked at his mobile screen and tried to see what he was so engrossed about. It seemed like an e-book and I tried to read a few lines to figure out what kind of book it was.
My eyes opened wide and suddenly I was awake with a jolt. It was an erotica story and to my bewilderment, a gay story from what I could gauge! I continued reading from the corner of my eyes and I was in a very interesting part of the story right now. I noticed his other hand was under the blanket, probably stroking his hard cock.
I hadn’t noticed the mature guy properly before but now that he had drawn my interest, I checked him out. He must be in his late 40s, probably even early 50s maybe.
He was a bit shorter than me, but not by much, 5’9″ or 5’10” probably. He seemed to have a well-maintained physique but receding hairline and gray hairs were showing his age. The guy had a light mustache and bit of stubble on his face, giving his otherwise very business-like appearance a bit of raw and rough manly edge.
As I steered my eyes back on his mobile screen, I realized that he had noticed. I looked up and saw him looking at me. He was visibly flustered, probably realized that I knew what he was reading. He looked a bit embarrassed as he quickly turned off his mobile’s screen and pulled his other hand out and kept on the armrest. I felt bad and also saw this an opportunity to break the ice.
“Seemed like a nice story”, I whispered, intentionally as a hint to let him know that I was into it. He didn’t say anything, so I continued, “Was it about a crossdresser?”.
He seemed even more flustered now, so I placed my hand on his hand and said, “Chill, I used to be one.” and smiled. That did the trick and he was now visibly relaxed. Finally, he spoke, “What do you mean, used to?”.
So I told him about my college days, and then marriage and how I stopped cross-dressing etc. He asked me, “But do you still meet other men?” and I replied, “Sometimes, yes”.
He was then silent a moment and asked me directly, “Would you like to spend a night with me?” and I could see the seriousness and lust in his eyes. I asked him about his whereabouts and when does he wanna meet for fun. I told him that I would definitely like to get fucked by him, but night might not be possible.
He smiled and said, “Trust me, you won’t regret the night. I stay at my daughter’s place in Mumbai, and she is out of town for 2 weeks, returning day after tomorrow. I am hoping that you can manage to stay for the night as I think my daughter’s clothes would fit you just fine”. That instantly gave me a hard-on. It had been years I have dressed up as a girl and got fucked. I asked him, “How about tonight then?”
As we landed, it was close to 1:00 am. I called my wife and told her that I have to first go to the office and I will get more late to come home. If it gets too late, I’ll take off the next day and come straight in the morning.
She was already in bed and half-sleepy so she didn’t mind or said as such. We headed to his place, which was just 20 minutes away from the airport. As we entered, he locked the door and grabbed me by surprise and pulled me closer. He planted his lips on mine and I gave in too as we kissed deeply.
He parted lips and walked me to his daughter’s bedroom. He opened her cupboard and said, “Take your pick, wear whatever you fancy. I use her guest room when I am in Mumbai, so I am gonna go keep my bags, take a quick shower in the other bathroom. You can use the bathroom here, get dressed and let me know once you are ready and I will come in”.
I nodded and he left the room. I took off my clothes and kept them on the chair. Then I took a quick shower and started going through the guy’s daughter’s dresses. She had some nice skirts and tops, but I opted to wear a sari. Something about sari is, it is extremely sexy. I picked out a slightly traditional looking green saree and a dark green matching sleeveless blouse.
I checked her lingerie drawer and found a nice pair of partially see-through designer bra and pantie in black. I was already too excited and even slightly shivering with anticipation as I put on the lingerie. I realized what he meant about his daughter’s clothes fit me. It seemed like she had a similar figure and size as mine with kind of small boobs, about A cup or so. So, her bra fit me quite nicely.
I wore the sari and put on some bangles and earrings. I also found a nose-ring in her drawer so I wore that as well. I lightly dabbed my face with a little bit of foundation and blush. And I put kajal in my eyes. I was not sure if I should wear the bindi as I don’t have long hair right now. So I skipped that. I just put nice pink lipstick.
As I was doing small touches to my appearance, I heard a knock on the bedroom door. I said, “Come in” in as much as girly manner as I could put in.
As he walked in, I turned towards him. He stopped in his tracks and checked me out from top to bottom. He looked like he was enjoying the view because his lusty eyes were almost undressing me on the spot! He was wearing nothing but gym shorts and had two glasses of scotch in his hands.
He extended one glass to me and asked if scotch was fine with me. Honestly, looking at his manly, hairy body with a hint of gray hairs and his semi-erect cock making a tent in his boxers, I had no time for idle pleasantries.
I took my glass and gulped down the scotch. As I smacked my lips, he was still standing there, still kind of stunned. I took his glass as well and emptied it in my mouth. But I didn’t gulp it down, I moved to him and locked my lips on his and he drank that scotch through my tongue and lips. “Wow”, he exclaimed as he broke the kiss. I was in his embrace as he grazed on my lips.
“You don’t like to waste time, don’t you? You horny little slut”, he quipped as he tightened his grip around me, “Alright then, I am not gonna hold back. One thing I didn’t tell you before.. I am gonna fuck your ass at least twice tonight”.
He pushed me towards the wall and pinned me as we continued kissing. After a few moments, we had to part our saliva dripping lips to catch a breath. He pulled down my pallu and opened my blouse. He started kissing my neck and went down as he simply moved the bra straps from my shoulders.
I was already super hard and in ecstasy. He freed my nipples from the bra and locked them in his mouth and started sucking on my left nipple hard while gently pinching my right nipple. His hand continued to play with my boobs. He kept alternating between my nipples the same way and my moans were getting louder and hornier.
While he was toying with my nipples, I grabbed his now hard cock through his boxers. “JACKPOT!!”, I screamed in my mind as I felt his rod. It was easily over 6-6.5″ from what I could tell, but really thick and with thick veins. I could feel the wet patch on his boxers on my fingers.
I pulled down his boxers and started stroking this marvellous ‘love wand’. He realized what I wanted and he stopped sucking my nipples. I went down on my knees. I took his big cock in my already drooling mouth and started sucking his big flaring head vigorously.
“Aaah, yes baby girl…”, he exclaimed as he started moving his fingers in my hair. I licked his entire shaft and spat on it, and spread it properly with my hand while stroking him in a circular motion. I looked at him and gave a naughty smile. I could see he was happy, and I was happier to be able to be in the dress and act like a slut.
I maintained the eye contact as I again took him in my mouth and started sucking him harder. He grabbed my head and started matching my motion and fucking my hungry mouth.
After a couple of minutes, he pulled out in haste. I figured he probably was getting too hot and didn’t wanna cum so soon. He pulled me up and started kissing me again. As he was kissing me, he started pulling my sari up. He completely pulled it up to my waist and squatted down. I held the sari up with one hand and my other hand was toying with my nipple.
He looked up at me, “Nice choice of panties, baby girl”, he said as he smiled. I smiled back, “Mmmm, you like it, daddy?”.
“Oh yeah, I love it”, he said as he freed my hard cock from the side. He stroked it a couple of times and then started sucking it. I was in heaven by now and I could only think how amazing it will be when he’ll be really pumping my ass. I suppose he realized it too. After sucking me for a few seconds, he turned me around and pulled the panties to one side and buried his face in my ass.
As his tongue reached my asspussy, I let out a heavy moan. He licked my hole thoroughly and made it wet. And then I felt his finger entering my asshole. He fingered me for a few seconds with one finger and then inserted two. He continued doing that as I was just going wilder, and then to three fingers. I could really feel my asshole gaping involuntarily in anticipation.
He stood up, pulled my pantie down to my knees and asked me to bend over. I obliged and placed my hands on the wall and arched my back. He took out the condom, put it on his cock and spit in hand as he smeared it on the tip. He placed his tip on my asshole, grabbed the sari around my waist and without any warning, he rammed his thick rod in my ass. I let out a scream and turned to look at him.
He was grinning and just said, “Don’t look at me like that, slut. I know you have taken hard fucking enough”.
I giggled and pushed my ass out and felt his balls touching my balls. He was deep inside me, all the way in. “That’s right, take it bitch, take daddy’s cock”, he said as he tightened his grip on my saree, like a bridle on the horse and slapped my ass.
“Uhhh”, I moaned and I moved my ass, “fuck me, daddy, fuck me now”.
He let out a grunt of approval and started pumping slowly, but only for a couple of strokes. Soon enough, he was fucking me really hard and every moan of mine was only encouraging him to slam harder.
“Phlat, phlat, phlat”, the sound of his body slamming against my juicy ass was driving me crazy and making me moan like a cheap whore. I was completely out of my mind, my body was moving on its own, matching his rhythm and taking that ass-spreader like a hungry bitch.
He slowed down again, and I was thinking, “thank god, I am out of breath”. But he didn’t slow down to give me a break.
He straightened me up and almost kinda slammed me against the wall. His cock was still deep inside my ass as he pinned me on the wall. I was sandwiched between him and the wall. His one hand took my hands on top of my head and held them together. His other hand was still holding the sari up my waist.
He soon started his hard fucking while kissing on my neck. I could feel his skin all over my back as he continued giving upward strokes in my ass. And with every stroke, he would grunt, giving it maximum thrust. I was moaning in unison with each deep stroke. He continued fucking me hard in that pinned position for a few minutes and suddenly took it out. I understood that he was at the climax.
I quickly turned around and got on my knees. I took my tongue out and looked at him like a hungry whore. He pulled off the condom and pushed his cock into my mouth. Before I could even start sucking him, he held my head back and started fucking my mouth.
Within a few seconds, I felt him reaching the tipping point. He stopped stroking and held my head with one hand. As he started coming, he took his cock out of my mouth. I took my tongue out as he aimed it and continued spraying his cum on my tongue and on my face.
Once he stopped, I grabbed his cock and started sucking the tip for every last drop of his warm man-juice. As I finished, he moved back and sat on the bed, panting. I spat out all the cum in a small handkerchief and wiped it off my face and lips. As I looked at him, he smiled, “You really are a slut.. my personal slut for tonight”.
He pulled me closer and started kissing me. I sat next to him on the bed and we continued kissing for a while. I slowly started removing my blouse and sari. After 15 minutes of making out, he was hard again. As I noticed his hardness, I made him lie down on the bed and sat between his legs to suck on this lovely man-candy.
I kept looking at him for approval while sucking him and I could tell he was enjoying it a lot. After a minute or so, he gestured me to turn to his side, in 69 position. I did the same as I continued sucking his cock. I thought he wanted to suck my cock as well but he wasn’t interested in that.
He again started tongue fucking my hole. Cock in my mouth and wet tongue in my ass, I was again going out of control. I could feel his saliva dripping down from my hole to my balls. I was very wet in my ass-pussy. I took another condom and placed it on his dick.
I turned around and sat on his throbbing rod. And I slowly took him inside my ass. I started slow, taking him nicely in and out, feeling every vein on his thick cock on my anal walls. But soon, I was in trance and started really getting pumped hard, as he started stroking my cock while I rode him. Since he had just unloaded, I knew he wasn’t gonna cum so fast, so I was enjoying this fuck session.
After a few minutes of riding, I moved and got on all four. He got up and came behind me and without blinking an eye, rammed in again. Even though I was taking him easily, that first stroke was quite amazing when he entered. He held my hips with both hands and started fucking me hard. I kept matching his rhythm and banging my ass on his body. After a few minutes of doggy style fucking, he pulled me up as he continued fucking.
He turned my head towards him and we both started kissing as his cock continued my anal exploration in slow motion. And then, he pushed me again down and he himself on top of me, pinning me again between him and the bed. I was flat on my stomach as he continued the slow fuck. I was quite enjoying this as well, pinned down but nice and rhythmic slow fucking.
After a while, I asked him to stop. I turned around on my back. I raised my legs and parted my ass-cheeks with my hands. “Fuck me a woman daddy”, I invited him. He smiled and inserted his cock in my gaping hole. As he slowly fully went in, he leaned over and kissed me. I wrapped my legs around his waist and my hands around his neck as our tongues continued playing with each other.
He started stroking and I started moaning like a bitch in heat. That only drove me more wild as he increased his pace. I knew that this was gonna be more than enough for him to handle and he was gonna come soon.
After a good 3-4 minutes of ramming my ass like that, he got up and pulled out his cock. He moved and stood over my stomach as he removed the condom and started shooting his load all over my chest and face. I managed to catch a few drops in my open mouth, but the rest of it was more than enough to drench my face.
He got up and stood on the side of the bed. I turned towards his cock and started licking him clean and sucking his tip. After a few seconds, it was too much for him and he pulled his cock out of my mouth. As I got up and sat in front of him on the bed, panting and extremely satisfied, he said, “Hold on, I gotta go pee”.
I grabbed his cock as he was about to turn to leave and gave him a naughty smile. He was puzzled as I got off the bed and knelt down in front of him. “You don’t have to go to the bathroom for that”, I smirked.
His eyes widened in disbelief, and joy, “Shit, really? fuck yes baby… let me wash your face”, He stood straight, and aimed his still somewhat erect cock to my face. I was extremely hard at this point and stroking my cock as he prepared to rain down his golden nectar on me.
He started a little bit slow at first and straight in my mouth and then he let the floodgates out. My face was flowing with warm piss, and washing the cum down all over my body.
I increased my strokes and instantly shot my load across on the floor in the pool of his cum and piss flowing down from my body. As I finished, I sat down on the floor, out of breath, with wet bra and taste of cum and piss on my tongue.
After a few minutes, I got up and went to the bathroom to clean myself up. By the time I came out, he had already cleaned the floor and put the lingerie in the washing machine. We didn’t say anything much as we continued tidying up the room. I folded his daughter’s clothes and kept everything as it was.
We had another round of scotch and smokes as I checked for Uber. He said that he usually comes to Mumbai only once or twice in a year. But next time he’s here, we can do this again.
I am surely looking forward to it, whenever next time may be.
