Chapter
7
A Bet
Later during the first year Amma talked to Appa about Vidhya. As is normal in any arranged marriage, my parents did a background check on Vidhya and found that she belonged to a thoroughly respectable family. Her father was a senior Manager in a nationalized bank while her mother was a housewife. She was an only child.
My parents met her parents and it was decided that although it was premature to go for any formal engagement, they were both going to permit us to be very good friends with each other. Each of us could visit the other’s house and be welcomed like family members. If, by the time we graduated from Engineering College, we still felt the same affection to each other, then we would be engaged immediately and married a few months later – depending upon identifying an auspicious time for the marriage.
Now in my fourth and final year, Vidhya and I still felt deeply attached to each other as we always did. It was almost a foregone conclusion in both in our families and amongst our friends and classmates that we would be married to each other within a few months.
It was during this time that I was challenged by a classmate to go to the Girls’ Hostel and spend a night in it without getting caught. Raja was a classmate who was in love with another of our girl classmates – Sarala - but till then had not dared to tell her about it. He was forever envious of me because I had already hitched my wagon to Vidhya’s and we were scheduled to get married to her later in the year. I knew that Raja wanted to tell Sarala of his love but had not dared to do so for fear of being rebuffed. I had talked about this to Vidhya and she had surreptitiously found out that Sarala also had a soft corner for Raja. Vidhya did not want to interfere in this matter for her own reasons. I wanted to help Raja because I was fond of him.
I told him I could accept that challenge but needed a little time to prepare for fulfilling it. He said that I had up to one month from that day to fulfill it. The reward for fulfilling it was that Raja would run around the campus during the day time on his briefs and vest once. The question arose as to what evidence I could produce as having spent the night in the Girls’ hostel. In a fit of bravado, I said that I would get hold of one of Sarala’s salwar Khameez sets. While I could spend the night in the Girls’ Hostel in Vidhya’s room, acquiring Sarala’s Salwar Khameez set was a little too daring an assignment.
I spoke to Vidhya about the challenge and she said she would try and help me out. A couple of days later, Vidhya met me in the evening after classes and outlined her plan:
I was to shave off my beard without which no one had seen me in Enginnering College. I was to dress up as a girl – like I had done on stage in school. I would stay in Vidhya’s room as her guest for a night. During the night, there would be a small accident when some water would be spilt on the spare matttress in Vidhya’s room. As Sarala’s room also had a spare mattress, I would shift to Sarala’s room. Later in the night, I was to get hold of a Salwar Khameez of Sarala’s and hide it in my bag which I would leave in Vidhya’s room. I was going to be Rajeshwari – a friend of Vidhya’s – who had an interview in the Engineering College for the post of the Principal’s secretary. Since the interview was very early in the morning, I had decided to stay the night in Vidhya’s room.
I needed Krishna’s help once again. I told her about the challenge and she said that she was game to help me out!
We brought down my old girl’s clothes from the attic and discovered that none of them would fit me now! So once again we went on a shopping spree – two sets of bras, saree petticoats, sarees and matching blouse pieces, a nighty, home slippers, skirt slip to wear under the nighty, bindis, makeup and so on. Krishna insisted I buy two pairs of panties as well. I told Krishna that I would wear my normal briefs under my clothes. She said that it was better to wear a small loin cloth of the kind worn by wrestlers in India and wear panties on top of it. I had seen this in films before and knew what she meant. I agreed and we purchased two sets of loin cloths in addition to two pairs of panties.
The same afternoon we had the tailor come over and measure me out again. This time my bra size had increased to 36C. It was a full grown woman’s size now. And I would look like a grown up woman. Luckily for me, not having shaved for a long time had resulted in my beard not being so tough. But it was a different proposition with my body hair.
Since getting caught would have meant complete humiliation and perhaps expulsion from college, I wanted to have full dress and makeup rehearsal before the actual day. We scheduled that for the day before the actual day and after classes. Both Krishna and Vidhya were to help me rehearse. For complete privacy, I was to leave my hostel room and stay the night in a local hotel. It was going to be the first time that Vidhya would see me dressed like a woman – and as it turned out not the last time. An hour or so before Vidhya was to arrive, Krishna helped me remove all my body hair – chest, back, arms, legs and even in the upper thigh regions. I had to do this while being stripped to my shorts.
We were just starting my make up when Vidhya joined us. She was very surprised to see how different I looked without my beard. Together, Vidhya and Krishna made me up and helped me to change into my blouse and Saree. As it was a new bra, I had to once again adjust the shoulder straps. Vidhya was quite surprised at my dexterity at doing that. I reminded her that I had had considerable practice when I was in school and that I had played many female character roles on the school stage.
By the time my hair was attached to my head, all the old lessons of deportment and mannerisms came back to me. And once I was fully dressed and ready, I was once again transformed into a beautiful young lady. If Vidhya had not seen me getting transformed, she would have been convinced that I was a woman to start with. I was practically unrecognizable and looked completely different from the bearded person I normally was in College. Both Krishna and Vidhya agreed that Sarala and all the other hostel mates would be completely taken in. Vidhya started addressing me as Raji which is the dimunitive for Rajeshwari – my adopted name for the purpose.
The rest of the day, we spent in my trying out my other costumes – the saree in which I was to walk in to the hostel, the nighty and so on.
Suratkal used to be a small place and everyone seemed to know everyone else. I did not want to be seen clean shaven by anyone – at least at that time. So we ordered food from room service and Krishna, Vidhya and I spent the rest of the evening and night in our hotel room.
The next morning, I woke up somewhat late. I wanted to catch up on my sleep because I knew it would be rather difficult to sleep that night. At the same time I had to be careful not to appear very puffy eyed.
In the afternoon, Vidhya returned to her hostel and Krishna helped me get ready.
I started with a very close shave. Afterwards, it was layers and layers of make up. The make up had to look natural. Anyway, if anyone was to ask me, I was going to say that I had blotches on my face because of a skin condition so I needed to apply thick makeup to hide it.
Once I was completely dressed, we put all my spare clothes into another small overnight bag. These spare clothes consisted of a bra, panties, a saree and a matching blouse and petticoat, a nighty and a slip to wear under the nighty. For good measure, Krishna added a half opened packet of Sanitary Napkins wrapped in a newspaper. When I asked Krishna about it, she explained that any lady always kept a few spare Sanitary Napkins with her. It would also look very realistic to have a packet in my bag.
We had arranged for a taxi to pick us up at about 6 in the evening to transport us to the hostel. We chose that late hour because I would have better chances of escaping close scrutiny in the evening than in bright sunlight. I could also closet myself in Vidhya’s room all evening saying that I was tired from the bus journey and did not want to stir out.
Both Krishna and I reached the hostel gate and luckily for us, we passed no one on the way. Anyway, no one in the campus had seen me clean shaven, much less dressed and made up to look like a girl, so the chances of recognition were very remote.
We entered the Common room and asked one of the girls who was there to have Vidhya summoned. She obliged and soon Vidhya was sitting with us and chattering nineteen to the dozen with Krishna. After I was formally introduced to Vidhya as Rajeshwari “Raji for short”, Krishna explained to Vidhya the purpose of our coming there.
Vidhya, for the record, said that she would be happy to allow Raji to spend the night in her room but she needed to take the warden’s permission for it. The problem was that the warden was expected in a few minutes. “I am sure the warden will give permission – I have seen so many girls bring their friends over during the weekend and for me this is the first time that I am bringing over a friend.” So saying Vidhya winked at me!
Krishna said that she was getting late so she would leave me with Vidhya. Vidhya suggested I could go to her room right away and wait there. So we walked through the corridor of the hostel to Vidhya’s room.
We passed a few girls on the way who smiled sweetly at both of us. We did not however pass Sarala. When we reached Vidhya’s room, she unlocked it and we entered it.
Vidhya’s room was much more neat than mine and I said so to her. “That’s because you were coming – I would not like you to see all my bras and panties and the rest of my clothes lying about here!” she said.
I could not resist it but I pulled Vidhya closer to me and kissed her on the lips – my first ever kiss! Vidhya was surprised, but returned the kiss after resisting just a wee bit! I had to be careful not to smudge my lipstick.
Vidhya told me, “You look beautiful and very, very feminine!” I thanked her.
Vidhya now told me to lie down on the spare bed and act as if I was asleep. If the warden came then I could continue to “sleep” as I was “tired from a long bus journey.” I did as I was told. This was the first time I was lying down in women’s clothes. I had to be careful about my pallu covering my breasts constantly. I turned my face to the wall and closed my eyes.
Soon I felt the bed shaking and discovered that Vidhya had climbed into the bed with me. The bed was really meant for one person so Vidhya had to lie down in close contact with me. I felt her breasts on my back. That and the women’s clothes gave me a huge hard on. I guided her hand inside my clothes and between my legs. Vidhya was surprised at the size of my penis.
“Is it normally so big?” she asked me.
I told her I did not know about others but mine was so big. Actually, I don’t have such a big penis even when excited but I guess since it was a first time for Vidhya, she thought I was bigger than normal.
I told her that she had to be careful, because the lump of my penis could be visible through my saree. I was also wearing panties instead of briefs which offer no compression for excited penises, the restrictive presence of a loin cloth notwithstanding!
After necking for a few minutes, Vidhya said she would go and check to see if the warden had returned. I turned my face to the wall and closed my eyes. A number of girls peeped into the room and left when they found Vidhya was not in. I could sense them looking at my back but since I seemed to be fast asleep, they did not disturb me.
Vidhya returned after what seemed like a long time and told me that it was all fixed up. The warden had agreed to let Raji spend the night in Vidhya’s room. I told Vidhya that I was genuinely feeling too tired for any dinner and that I wanted to change and retire for the night. She agreed and I opened my bag.
Vidhya noticed the Sanitary napkins wrapped in the newspaper and asked me, “Whatever do you want that for?”
I told her it was Krishna’s idea to make me appear even more feminine because she said that women always had a few spares with them all the time.
Vidhya said, “Very smart!” and smiled at me.
I took off my saree and my blouse and slipped the nighty over my head, careful not to disturb my false hair. Then I pull up my nighty to the waist and undid the knot of the saree petticoat and loosened it. The petticoat fell at my feet. I stepped out of the heap of clothes at my feet, reached for the half-slip in my bag. Once again I pulled up my nighty and stepped into the skirt slip, adjusted the elastic band on my waist and then pulled down my nighty.
Then I sat down to fold my clothes, first the saree which was a chiffon, then my blouse and then my saree petticoat. Vidhya made a few corrections in the way I folded my blouse which is a very complicated garment to fold.
I wanted to go to the toilet to brush my teeth before going to bed. I asked for directions and found the toilet which was a few doors down the corridor.
There was one other girl in the toilets. She was wearing just a white bra and brown panties and was shaving her legs. I noticed she had a terrific figure. My entering the toilet did not disturb her much, except that I was an unfamiliar face. She asked me who I was and I explained that I was Vidhya’s friend, Raji and that I was spending the night in her room. She introduced herself as Sarala. With great difficulty I managed not to react visibly!
I finished my use of the toilet and returned to Vidhya’s room. Vidhya returned from her dinner in a few minutes.
I asked her about Sarala’s apparent shameless cavorting in the common places in just her underwear. Vidhya explained that Sarala has been like that ever since she came to stay in the hostel in the first year. “She is a bit of an exhibitionist,” Vidhya explained.
“Is that why you are not too fond of her?” I asked Vidhya, who nodded.
“I am going to try and sleep now” I told Vidhya. “Give me a goodnight kiss!”
Vidhya came into my arms and we kissed each other eagerly on the lips. I asked Vidhya if she wanted to go any further. She said “No.” I said, “let me at least explore you with my fingers.”
At first she said no, but when I continued to kiss her and found she was responding to my kisses, she agreed only to fingers….
… Well, to cut a long story short, I managed to have Vidhya climax once – her first time she blushingly admitted - during that session by just using my fingers. She loved it very much but blushed when I asked her about it repeatedly.
Around two in the night when the entire hostel was asleep, we put our plan into action. I first switched on our light. Vidhya then fetched a glass of water and poured it on the mattress on which I was previously sleeping.
Vidhya then sought out Sarala’s room and knocked on it. Dressed in a nighty Sarala opened the door. Vidhya explained that when I groggily tried to pour water into a glass to drink, I spilled it on the mattress, so could I sleep over in Sarala’s room. Sarala had no problem about that, except that I would need to clear her clothes off the spare mattress in her room. I said I did not mind and thanked her for it.
I went back to Vidhya’s room and returned with a pillow and a coverlet for myself. By the time I returned to Sarala’s room, she was already fast asleep in her bed. I noticed that Sarala had taken off her nighty and was once again dressed only in her bra and panties. Placing the pillow and coverlet on one side of the bed, I carefully moved all of Sarala’s clothes to the chair and lied down. I opened her cupboard to see if I could keep her clothes inside. I noticed that the contents of the cupboard were just tossed higgledy-piggledy and there did not seem to be any attempt to classify her clothes in any particular way. Getting a hold of one of Sarala’s Salwar Khamez set was going to be very easy – she would not miss it at all.
After I had cleared Sarala’s bed, I lied down on it and covered myself. I could not but help stare at the pattern of the bra strap on Sarala’s back. I noticed that she had a small mole on the left cheek of her buttock.
As I was feeling tired, I fell asleep soon enough. I am in the habit of waking up with the light and I woke up similarly this morning too. Being a Saturday, the hostel was quiet. Everyone seemed to want to sleep till mid morning.
Without making a sound, I sat up, and folded the coverlet. Taking care to leave it partially open so that, I could conceal the one set of Sarala’s clothes in it, I tiptoed to the cupboard, opened it and picked out a set which I had seen Sarala wear in the second year. I noticed that it was stained brown at the crotch. Taking care not to touch that part, I folded it into a bundle and placed it on my coverlet. I rolled the coverlet in such a way that no part of the Salwar Khameez was visible outside and opened the door of Sarala’s room. Finding that no one was in the corridor, I tiptoed back to Vidhya’s room.
Vidhya was already awake and dressed. The first thing she asked was “Did you get it?” I nodded.
Quickly I took off my nighty, slip, panties and bra. Opening my bag, I located the second set of bra and panties and quickly wore them. On went my other saree petticoat and blouse and then finally the saree. I fixed my makeup quickly and adjusted my wig. Putting all of my other clothes into the bag, Vidhya and I quickly walked to the main doors of the hostel where our taxi, as instructed, was waiting. Both of us got into the car and had the driver drive us back to the hotel which I had left the previous day.
Without incident, we reached our room. I quickly removed my saree, blouse, petticoat, bra and panties. Vidhya helped me out of my wig. Tying a Bath towel round my middle, I went into the bathroom. I cleaned my face of all the makeup and had a cold shower which woke me up fully. I realized I was still having a hard-on from the Raji disguise.
I stroked myself and soon I was feeling a tingling down my spine. I did not know what was happening. A little scared, I called out to Vidhya who I asked to come into the bathroom. One look at me and she knew what was happening.
“It’s time for me to return last night’s favour” she said. I did not know what she wanted to do. But soon she was stroking me, pulling my foreskin back and front. Within no time I climaxed – my first time.
I joined Vidhya in the hotel room after completing my bath. She teased me a lot about my climaxing. I teased her back about the previous night when my fingers had worked their magic.
It turned out that Vidhya got turned on by men dressed up as women. And the sight of me dressed up as Raji, turned on Vidhya so much that she could not resist climbing into bed with me. I told Vidhya that wearing women’s clothes turned me on, so after marriage, we could have great sex life. She agreed too.
The Monday after that I was subjected to a lot of teasing and ribbing when I returned to classes with a clean shaven look instead of my bearded face. Since classes were ending that same week for the final year’s exams, I did not have to face the teasing for too long!
At the end of the week on the last day, I told Raja that I had fulfilled my bet and that I would give him Sarala’s Salwar Khameez to him on the last day. He was curious to know how I had managed it. I refused to tell him anything.
As agreed, on the last day, I gave Raja the Salwar Khameez set which belonged to Sarala. Raja had seen Sarala wear those clothes in our second year so he could not controvert that the clothes did not belong to Sarala. The same day, our campus was treated to the sight of Raja wearing just his briefs and vest running around the campus. To date, neither Raja nor Sarala – who are now married to each other - know how I managed to lay my hands on Sarala’s clothes!