Hello ISS readers, I am Raviish and I reside in Mumbai. To briefly tell you about myself, I’m currently 27 years old, married and I’m a closet bisexual cross-dresser. I’m 5ft 11″ tall, average built with long legs and average personality. When I say average personality, I mean that I neither look too masculine nor too feminine, just your regular guy. I like both girls and guys, but I like to be bottom with guys. The story I’m going to present to you today is about an incident of me losing my virginity, when I was 19 years old. I was brought in touch with my feminine side when I was in my junior college (age 18), by my private tutor’s husband. He was the one who let me finally act on my deep desires and got me into cross-dressing. However, we never had sex, due to various reasons… like my age, my hesitation for anal etc. Anyways, that will be a separate story altogether. Let’s fast forward couple years when I was 19 and finally lost my virginity, to a cop.
It was a cold, slightly rainy night in July and I was travelling back to my house in a local train. It was around 12:15 or so in the night and train was practically empty. I was getting back from a party and had a nice buzz from the drinks. After couple of stations I got bored sitting almost alone in the compartment, so decided get some fresh air standing in the door. There were probably 4 other people in the compartment and two of them were asleep, another was busy reading newspaper at the farthest end and last one was sitting at the window across him. After I got in the door, a man boarded the train at next station. He got in and stood near the opposite side door.
After couple of minutes I just glanced across and I thought I noticed him checking me out, head to the toe. Naturally, it felt weird, but I checked him out too. He was a slightly over the middle-age man, maybe in his late 40s. Average looking, slightly dark/wheatish but tanned skin. He was wearing a beige half-sleeve shirt and dark brown pants with a messenger bag on his shoulder. Basically an average guy you would otherwise not notice. Then I noticed his shoes. Now, those who are raised in Mumbai will know that Mumbai police wear a distinct type of shoes and are easily recognizable. I understood he was a cop and then I thought to myself, “why would a cop check me out?” I realized that I was wearing a bright orange/pink shaded short kurta and rather tight thin-cotton jeans.
As I said earlier I don’t look very feminine, but that attire wasn’t very manly. Plus I was standing bit girlish in the door, with one hand on the hip and my left leg slightly crooked. “He might be thinking I’m some kind of freak…”; I thought to myself and suddenly our eyes met. Not sure what to do, I simply gave a smile and turned my head and moved near the pole in the center of the door. It was drizzling lightly outside and the cold air and light waves of rain was forcing my top to cling on my chest, making my nipples pop. Suddenly he came near the door and stood in front of me, with his back on my side and he held the pole behind him. I thought he would be getting down at next station. Next station passed and he was still standing there… as soon as train passed the platform, he turned sideways and relaxed his shoulder on the pole. I was still standing with my body straight close to the pole. Slowly I felt his fingers trying to slid down on the pole, gliding over my tummy, barely touching but close enough for me to notice.
He stopped right near my crotch and a chill ran through my body. His index finger was making small circles on my crotch and it didn’t even take me 3 seconds to get hard. I raised my eyes and looked at him and he was looking at me, measuring my every reaction. There was a wild lust in his eyes, wild yet very sensual. The train was nearing the last station, apparently destination for both of us. Usually, I would have not even bothered about him, but I guess the combination of rain, cold and bit of an alcohol was adding to my already slightly horny state. I thought, it doesn’t matter… as long as he’s got a cock to fill my mouth with hot cum, a quickie should be good way to close this day.
I smiled at him as he had started to get more fingers running across my hardened rod over my tight jeans. He smiled back and whispered, “You got time?”… I gave him the best slutty smile I could and went closer to his ear. Making sure I breath enough air on his ear, I whispered back, “time and place, both” and gave a quick lick on his earlobe. That was enough to seal the deal and as soon as we got down from the train, we were on the way for one wild night. My friend had his office near the station and I had spare keys as I used to use his office for my project work. Since he knew I work mostly at night time he had given me keys to use the place.
We got inside the office and I made sure to lock it back from inside. I knew nobody would be coming to disturb us but this was the first time I was doing this outside anyone’s house, so it never hurts to be extra careful. As soon as I locked everything, I turned off the lights and turned to my lover of the hour. My friend’s office is on the second floor and through the blinds the street light and lights from neon hoarding was mood-lighting the room. It started to rain outside and the mood was setting up very nicely. We started taking each other’s clothes off slowly while making a small talk and playful kissing. His name was Dhanwant and he was head-constable in Mumbai police, he was 46 but he had, what I didn’t notice earlier in his plain clothes, a well built and maintained body.
He wasn’t bulky or heavy, but well chiseled. I told him that I do everything but anal… and to my surprise, he was absolutely fine with it. There was a weird and wild passion in his touch, but he wasn’t rough or hasty in his behavior. He was, treating me, like a lady and not a slut or cheap whore. I was now enjoying it even more and slowly our talks got less and kissing got more. Soon we were exploring each other’s tongues and drooling saliva on our chins. As I was really getting into my horny nymphomaniac girl character, he lowered his lips on my nipples, as if sensing my need. He started sucking my left nipple, making rounds around it with his tongue while matching the same rhythm with his finger on my other nipple. This man… ohhhh, this man knew how to handle this girl.
By now I had started letting out my moans, “Aaaahhh ssssshhh mmmm” and that seemed to drive him even wilder. Slowly both my nipples were getting handled by his fingers, slowly caressing, sometimes slightly pinching but never too much. He moved his tongue from between my bare chest and licked all the way down to my navel and soon his tongue was exploring my navel cavity. The rain outside was now getting heavier and my head was getting lighter from the all the sexual euphoria that was I experiencing. I decided to take control now, so I turned and pushed him on the table. I went straight for his undies and got rid of the final obstacle between his manhood and my horny mouth. As soon as I removed his undies, my prize sprung out, standing straight with the head glistening with pre-cum.
He had a nice muscular rod, about 6.5″ in height about 2/2.25″ in circumference. It was exactly like my cock, only slightly dark in color. Even though I love sucking big and/or fat cocks, I couldn’t have asked for a better cock. He clearly was enjoying me so far cause his little soldier was oozing out little too much of pre-cum. I wasn’t going to let all that sweet juice go to waste, so I started from the bottom. I started licking his balls and bottom of his hot rod, where all the pre-cum was getting deposited. He had a nice clean shaven crotch and I love the men who like to keep their privates clean and at least less hairy, if not clean shaven. My tongue was getting hungry for more as I went on licking his hardened muscle of pleasure and tasting all that strong flavored pre-cum covering it. As soon my tongue reached his throbbing head and rolled around it, he let out a load moan. Without wasting a time I wrapped that wet chocolate bar with my hungry mouth and started sucking him. I could feel his breathing getting faster and I looked up.
He was looking at me with hungry eyes and my eyes met his with the same hunger. I kept staring at him while sucking his tasty dick as his hand reached around my head. He moved his fingers through my hair and held my head gently; he eyes were asking if he could go further. I stopped sucking and let his full rod in my mouth to the point where his tip was touching my throat. I had learnt to control my gagging somewhat so I didn’t have much problem of taking full dick in my mouth. He started fucking my mouth, first long and slow strokes and then slowly increasing his pace. Despite my gag control, he was letting me take a break and catch my breath in between.
After 10 minutes or so, he let my head go and let me take control back of his dick. I knew what he wanted so I started jerking his rod at bottom and let my mouth & tongue work its magic on the head. After 3 minutes or so, I felt his body getting stiff, his legs getting closer together and his stomach getting hard… I knew I was getting my reward. I increased my pace and started rolling my tongue around his head fast, like a hungry cum-slut. His hand reached my head and grabbed it and he let out a loud moan. First load of his hot and thick cum shot through my mouth and filled it up in a second, but I had underestimated my gifted lover.
For the next 7-10 seconds torrent of his man-juice kept shooting and pretty soon my mouth started overflowing with rest of his cum covering my face and dripping from my chin. I kept sucking him till his little soldier went flaccid. He was breathing heavily and I was smiling with cum-covered face. I started collecting rest of the cum from my face and started licking it. I usually don’t mind not getting reciprocated as long as I get my reward of mouthful of cum, so I was now concentrating on licking the juicy cum and about to pleasure myself, but once again, I had calculated him wrongly.
He made me stand up and laid me down on the table and went immediately to work. He started where he had left off earlier, with his tongue in my navel and his fingers on my nipples. Soon he raised my legs higher and parted them. His tongue was now exploring my crotch and licking my pubic region around my rock hard cock. He probably didn’t like to suck cock as he just licked my shaft & head with his tongue couple of times and again went back licking around my balls and underside. I didn’t mind as he was damn good with his tongue. Meanwhile I continued licking rest of his man-juice from my face and chest while enjoying his mouth around my privates.
He raised my hips higher and before I could register, the wave of pleasure like I had never experienced before, shot through my body. His tongue was now in my ass crack and soon exploring my virgin asshole. I have never had rimjob before and this was something very new for me to experience. I would say that in that moment I felt, what I had imagined my girlfriends must have felt when I licked their pussies. I would say that, in that moment I felt that my asshole was my man-pussy. He continued rimming my man-pussy with his tongue and my body was now acting on its own. My anus, as if having brain of its own, opened itself and let his tongue in.
I was now on completely different level of ecstasy. He continued tongue-fucking me for, not more than a minute or so, and before I could realize, I was shooting my load all over my body, without even touching my cock once. My jizz was now sprayed all over me, from my stomach, to my chest and some drops even made it to my mouth and face. I was moaning like a crazy nymph getting fucked by 4 men on her first night. Never before I had been so aroused, to ejaculate, and that too so much, without jerking myself off. By the end of it, I was panting like an overworked whore while he came on top of me and kissed me deep. We rolled his cum in and around our tongues as he pushed it deeper in my mouth with his tongue. I sucked his lips clean as we parted our kiss. I could see his smiling face with sweat running around his face and dripping on me. I looked into his eyes and I decided… I want to get fucked by this man. I want him to make me a woman and I want it tonight.
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To be continued…
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Please feel free to comment and let me know if you liked my story. If any of you guys from Mumbai want to have some fun sometime, don’t hesitate to let me know in comments.