A crossdresser experience – Part 2

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Hello readers, I am Anupama, also known as Anupama. I am sharing my second experience. Before you read this, I suggest you go over the first part.

After the first experience, we didn’t speak for the next whole week. Over the weekend, I started to feel itchy on my bottom. Seriously, it was last week’s side effect. After a few days, I planned to cross-dress and go on solo outings as suggested by my friends.

I had the confidence, but I was still afraid. I started with less crowded places such as parks and restaurants. Next Sunday, Cross-dressed in Kurti and Leggings, covering the head with a scarf, went on shopping to buy cosmetics, and then visited a Park.

Ravi accompanied me, and as it was afternoon, the place was deserted. There was hardly anyone. I saw a couple roaming, and that interested me a lot. They occupied a corner space and just waited for the opportunity. Ravi, by my side, touched my hands, and that just aroused me.

Me: Ye lovers park hai? (Is this lovers’ park?)
Ravi: Ha (Kind of!)

We sat in the shade of the green Ashoka and kept an eye on the couple. The girl removed her scarf, and the boy pulled her closer for a romantic kiss. They smooched, and the scene sent shockwaves. Ravi, by my side, pulled me behind the thick Ashoka tree, grabbed my head and forcefully kissed my lips. I hesitated a bit, but the forceful kiss had another level of enjoyment.

My hands held him until his lips relaxed after sucking the red, glossy lips. He untucked his pants and underwear, and his dick popped out, handed over in my hands for a sexy handjob.

I stroked until it became hot and played with the foreskin, pulling it up and down. He made me kneel and stroked the dick head in my mouth. Just a few seconds later, tiny cum droplets started to pour out. I removed it. I came out with a big load of hot white cum, giving me a facial.

Ravi: Sundar lag rahi ho. (You are looking beautiful !)
Me: Shut up!

I cleaned myself, but on a serious note, I started as a voyeur and never expected to end up with a sexy smoky facial. Well, this small unexpected hook-up made me feel wanted and desired. He had started to consider me as his fuck buddy.

My Mother visited my place, and this time she requested a sightseeing tour to different places near the city. I planned a 2-day trip that included an overnight stay in 3 3-star resort. I reached out for Ola and Uber, but they seemed costly, so I finally consulted my fuck buddy Ravi.

He accepted the trip and helped me plan the itinerary under one condition, which was risky, very risky, but adventurous enough. The feeling of spending the entire night with a hook-up guy sent a shiver down my body, ignited an intimate level of closeness and fun.

On the First day, we visited a temple, a lake and in the evenings, checked into the resort. It was a private cottage on a triple-sharing basis. After dinner, my mother took her medications and within a few minutes she fell off to sleep.

I quickly changed into Green Lehenga and Choli, did my makeup, wore a bracelet and necklace and finally put on wedge sandals. Ravi was impatient as he continuously texted me and sent a favour request. I looked in the mirror and it was perfect for the evening.

I opened the door and pulled Ravi in. Without wasting any time, I removed the chunni to invite him, and in a second, he was in my arms. He planted a kiss on my lips, and our lips locked for some time. We played with each other’s tongues.

We later held each other in a French kiss pose until my entire lipstick got washed away. However, it was just the start of my female mode, and I expected a lot of foreplay to make me do crazy things later. I undid his vest and down came the lungi, exposing his dick.

I immediately started to suck the brown meat. At the same time, my hands caught the swinging hairy brown balls. As usual, my mouth couldn’t accommodate it entirely, so Ravi pressed my head inwards to have the shaft fit till my throat, and started to fuck my mouth with speed.

The saliva-clad dick consistently hit my throat tube, making me uncomfortable, and I had to exhale it quickly. I gasped, spitting out saliva, and could see Ravi moaning with pleasure. With the dick resting on my face, I sucked his sweaty balls, which added to the temptation, making his legs shake with pleasure.

It was his turn to pleasure me. He started with wild foreplay, kissing my neck and cleavage. Slowly removed my choli and licked my neck, shoulders, armpits, back, everywhere, making me moan. Removed the bra straps and sucked my breasts. I pressed his head hard as his mouth licked the nipples.

“Ah, Suck them more”, I ordered, and turn by turn, they got bitten, sucked until the skin turned red. There was a lot of tension at the bottom, and anytime my dick could burst out.

Ravi asked me to get on the bed, and I came in Doggy pose, lifting my ass while being on wedge sandals just as seen in porn. I asked him to lubricate my ass first by licking, he licked it with his tongue, giving me wild moans, “WOW”, “AAAH”, my wet asshole became gentle. It helped me reach to ecstasy.

Then poured coconut oil by inserting his index finger and repeating again with his middle finger. It hurt as it was burning inside. However, the fun and pleasure can’t be ruled out. He used a condom and lubricated the hard rock dick enough to be able to insert, and with the first stroke, the head was in.

I yelled, OUCH!” It was tough, then again, a couple of strokes till the entire dick was in, I was in extreme pain, but it turned into pleasure when he started to fuck. He grabbed my waist and started to drill more speedily. One big thrust and I could sense his pubic hair touching my hole.

My dick lost patience and sprinkled cum while Ravi continued to fuck my ass. There was no stopping him; my legs started to tremble, and I fell on the bedding. Ravi still managed to get hold of my ass and fuck me while holding my hands; his pubic hair added a rocking sensation.

In contrast, his legs pressed his dick harder in my ass, and after some time, he reached orgasm and started to release hot white cum in the condom. He ejaculated a big load and lay still until his balls got emptied.

He turned me and removed the condom that got filled with his cum, the dick started to get numb and now could fit in my mouth, I sucked the cum covered dick happily and cleaned it with my saliva, OHH it was just amazing. We took a break thereafter.

An hour later, I got up to clean myself and found Ravi missing. After searching, I found him sitting in the front lobby of the cottage with drinks. He had just started. In order to tease him, I did a little makeup, applied lipstick and deo, and put on some clinking metal bangles.

With no shame, I walked out nude in sandals in order to surprise him.

Me: Kaisi lag rahi hu (How am I looking?)

Ravi: Huh! (weird reaction)
Me: Chalo, asli jaam ready hai (Let’s go! Your real drink is ready)

Ravi was quick enough as he caressed my ass until we reached our bedding, and pounced on me. We were on the bed, he kissed my lips and could smell the intoxicating liquor, but he had to continue. Within seconds, his dick got erect and tickled mine.

Both erect ones are fighting for supremacy. We took turns to turn over each other until he broke the kiss. I ordered him to take me in missionary, I lifted my legs, he stroked his head in the hole. It was tight again and had to be lubricated. He applied oil and inserted it further.

I was in pain, and I groaned. With further strokes, I groaned more. He came down, held me and started fucking in missionary. It was painful at the same time since I was trying for the first time, so no pain, no gain. His legs exerted powerful thrusts, making me moan louder.

He held my legs tightly and fucked with good speed, at the end I sprinkled out on myself that spill on the mattress and asked him to do so, he tried and again gave a big load enough to be deposited in and out of the ass as well as on the mattress.

My ass was burning and turned red with the wild, wild drilling. Thank god, it didn’t bleed. I never imagined that I would be able to take a big load.

We had a thoroughly entertaining session as we both satisfied each other.

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