Long sex story 8211 I Was A Reluctant Shemale
- 2 years ago
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Hi !! ISS Readers. This is Pranavi, age 25 with an average height of 5’4”. About me, a very shy girl, studious with a little bit of village backdrop. This incident happened 3 years back which has changed my entire lifestyle. And to the people, who don’t believe, please trust me it was my true life incident.
Also this was the first time , I’m sharing this incident to you.
Now, coming to the point, I have finished my B.E and was placed in a reputed organisation in Bangalore and used to stay in a hostel with two other roommates, in which one girl was known to me and the other joined two months after we joined, who always used to be on mobile talks.. Suddenly my friend got a transfer & moved to Delhi,I had to stay with my other roommate Shalini. Slowly we became more intimate & used to share all the issues including personal.
Shalini was 3 years elder than me and had a boyfriend too. She used to talk to her boyfriend in the nights, (sometimes quarrelling) and used to discuss with me all the issues about their relationship. At times, while sleeping I used to see shalini’s hand under her skirt while talking in the phone, but strangely she used to lick her fingers after that and this used to arouse me a bit. Being a shy girl I never used to even change my clothes in front of her, but she was very free type and many-a-times I have seen her private parts (I used to like it too).And to be frank her assets are bigger than me & nicely shaped with good maintenance. Slowly, I have changed myself after seeing her, and used to sleep in skirts & t-shirts, going to beauty parlours, etc…
One day I was very tired in my office and slept early than the usual. Since I have not had my dinner, may be because of hunger I was awake in mid night with some murmuring sound besides me. As usual I thought it was my roommate talking with her boyfriend. But this time the sounds are a bit different & I could hear them as sweet moans. They both were discussing about their last week’s outing at one resort. By their conversation I came to understand that they had sex many times and also they were planning to have sex again at his place. By listening all of these things, I had decided to change my room next day morning, thinking that sex before marriage is a sin & staying with such kind of girls is more sin. But all this time I was still in a sleeping position and she was unaware that I ‘m awake. I was unable to get sleep by her moans & was cursing her for behaving like this.
Suddenly, I felt a hand on my left lap rubbing gently. And I noticed that, her hand was moving a little deeper & touching my inner thighs. At first I thought of getting up, but I was a little afraid & laid there silently. This continued for about 5 minutes and I was getting turned on by the warm feeling of her hand on my thighs.I wanted her hand to touch my pussy, but my conscience said that it was not right, that too with a girl. This had continued for another 5-10 minutes and she got up, went to the bathroom & then she slept. After I confirmed that she was in her good sleep the image of Shalini putting her hand under skirt came in to my mind.I slowly inserted my hand into my panty and started rubbing,I had a different kind of pleasure in doing so & continued it for long time & slept like that. Next 2 days went normally with loads of work in office and on the third day being Friday, we were chitchatting in our room after having dinner. After discussing many topics the main topic came (sex) and she asked me whether I had sex anytime & for which I replied strictly no. Then she asked me at least did I have romance kind of thing with any of the boys,I simply answered her that all these things would be after marriage. Like this our conversation went high & in turn I asked her about her experiences, if any. She told me that she & her boyfriend are having sex regularly and also told me that it was not a mistake as they are about to get married as their parents also agreed.
She asked me whether I have masturbated any time, and I said no. She then laughed and said that she has seen me masturbating. I was a little worried and said never I have tried such things. She immediately told me that three days earlier she had seen me putting my hand under my panty and also told that night she was aware of me listening to their conversation and told that she intentionally put the hand on my thigh. I was very silent and lowered my head downwards with shame. She then explained that there was nothing wrong in knowing such things and that too it is very essential especially for girls to know about Sex before marriage. By this time I was a bit comfortable and told her that even me too was interested in knowing such things, but was afraid.She then placed her hand on my shoulder and said you are my dear friend and I will help you out in knowing all these things. I was relaxed by her words and she asked me to remove my t-shirt and I denied. But somehow she convinced me and I removed it.Now I was in bra, later on she removed my bra too. She was completely dominating me & I was unable to tell her not to do to what she was doing. She massaged my back ,now she told me not to be shy and said that my boobs are looking good with some hair at the nipples. I replied not to tell a lie as I know that her boobs are much better than me and even bigger in size. She then removed her top & revealed herself. By comparing I came to know that, being small mine are looking cute than her. She then touched my nipples and squeezed a little. I moaned in pain and she asked me about the feeling, I said I am feeling a tickling sensation.
She then removed her panty and stood naked in front of me. Her pussy was neatly shaven with very little hair on it. She then inserted one of her finger and moved up and down. It was very juicy and by that time her finger was full of her love juices, she then licked the finger and told me to do the same for pleasure. I hesitated initially to remove my panty as it was not shaven (I don’t have a habit of shaving).In fact I didn’t knew that girls shave there. I told her the same thing that it was unshaven. But she told me that it was not a big thing and also some people like the girls with hair on their pussy, like her boyfriend. And she told me that she doesn’t like to be with hair though her boyfriend likes a lot. After that I inserted my finger into mine and masturbated. We continued this for 15 more minutes . After this incident, we became more closer to each other and daily while talking to her boyfriend she used to keep the phone in speaker mode and from the other side he used to talk dirty and we used to masturbate on hearing him. He didn’t knew about me masturbating alongside with his girlfriend while he’s on call with her.
After few days, she told me that she was going to her boyfriend’s house on the coming weekend as nobody was there. About him, He is Rajiv, handsome guy with a height of 5’10”, with athletic body structure, very calm in nature. I met him two to three times in restaurants. He is staying with his brother in a two bed roomed flat nearby and now his brother is going for an on-site to Australia and will not be in India for 3 months. I was a bit dull as I have to stay alone in the hostel for the weekend. That day passed and she returned back on the next day & looked very tired. I asked her the reason but she told nothing like that. But my thoughts were about them like how they have enjoyed the full night. Meanwhile she slept and I was unable to sleep due to the anxiety. Suddenly the doorbell rang and it was laundry man, so I gave my clothes and in an intention to give her clothes I opened the bag which she has taken to rajiv’s home. In the bottom I found her bra in two pieces. I was shocked but was covering my expressions and i sent the laundry man without her clothes. I was amazed by thinking about him that how come such a calm guy can he be very wild tearing the dress. Thinking all this I slept beside her.
In the evening once again I asked her about the last night and she replied that they had enjoyed in full extent in all the angles. Then I asked her what does she mean by angles?? She laughed at my innocence and replied that I need to learn many things. She then told me to search for a good boyfriend and gain all the practical knowledge before I get married, and also threatened that my husband may leave me if I was like this. I was a bit worried and said that her parents are very strict and if they come to know that she is with a boy it would be very dangerous for her. She then told me that now we are grown up and we need to manage things by our own without knowing to parents,and also assured me that she will search a good one for me for teaching me all of this. I was tensed but somehow I liked the topic and wanted to continue, but she told me to sleep as it was too late.
Some days passed on, one day there was no power in our hostel due to some electrical problem, the warden came & told that power is expected only by tomorrow. All the other girls are moving to their friends places nearby, but I was confused what to do & was waiting for Shalini to come from office. It was already 9 PM and she came. After seeing the situation she told me, let us go to Rajiv’s home for that night. I was hesitant in the beginning, but there was no other option for me as it was a hot summer. Then we went to his house, had dinner on the way to his house & by the time we reached there it was 10’O clock in the night. Being a two bedroom apartment, we both stayed in one bedroom while Rajiv was in other. Then it came to my mind that we have not brought anything to wear at night. As I told she is a very free type girl she removed her top and slept with only bra on her. There was one nighty of hers and I took that and slept.
As it was a new place I was unable to sleep and turned towards her and found she was not in the room.I thought that she might went to bathroom, but even after 15 minutes she was not back,then shalini’s words came to my mind about their enjoyment and wanted to see what they were doing. Slowly got up and went towards their bedroom, but the door was locked inside, I was disappointed but my inner desire wanted to see inside the room. So I searched for other options. To my luck the bedroom was next to kitchen & there was a ventilator on top which is reachable from the cooking platform. So I climbed it and peeped inside. It was really shocking for me, he was standing in front of her & Shalini was sitting on bed with his dick in her mouth. It was the first time in my lifetime that i saw a penis. She was taking the full thing in her mouth and licking his balls. Meanwhile he was pressing her boobs with both the hands and they were moaning in pleasure. By seeing the sight I was feeling some itching in my pussy and inserted my finger. After some time I opened my eyes and seen inside. By this time both were nude and she was bending to the front side with his dick in her ass. I wondered how much the big tool can fit into the ass, but got more excited by the scene. He fucked her for more than 10 minutes and reached their climax. I understood they were finished and got down and went to bed. After about 20 mins she came inside & slept.
The next day morning she told that she was having body pains and doesn’t want to go to office, me too was not in mood to go to office & we decided to sleep again. At about 11 we got up and by this time Rajiv was preparing something in the kitchen. We entered in the hall he told us to get fresh as he has prepared some breakfast. While having the breakfast I found he was observing me. I too kept an eye on him, after seeing his dick I was a bit disturbed and to be frank I was attracted to him. He was seeing my underarms and I realized that being a sleeveless nighty, my thick hair was protruding outside. I felt a little ashamed and suddenly her words came in my mind that he likes girls with hair. Initially I wanted to hide from his looks, but later on I wanted to show him my assets as I was horny after the last night episode. Finally, we finished there and went to our hostel.
The next week when we were chatting, the topic of sex came (she raised this time). After few talks she told me that she had searched a good teacher for me and told that classes would start from this weekend. I was excited and asked who that is? But she replied it was a surprise and assured i will be happy with the teacher. Finally the weekend came & I dressed well and waited for her to come. At around 7’O clock she called me & told she was held up in traffic & will be coming directly to Rajiv’s house and asked me to come there. I was a bit confused but somehow managed and reached there. Rajiv opened the door & welcomed inside. I was a bit tensed and sweating. He gave me some drink & we were talking about something the doorbell rang & it was Shalini who came alone. After settling down she asked me how the teacher was. I am confused and asked who that was. Suddenly Rajiv came & sat beside me, holding my hand. I became nervous and again started sweating. I was not comfortable there and stood up. Immediately she caught me by hand and told that she has searched for many and finally thought Rajiv would be the correct teacher and as they were getting married they both had no problem with thsi. She also told me that definitely she would learn the best things from him so that she can impress her husband in future. By this time I was ok & started thinking. She took hold of my hand and drove me to the bedroom. I was simply following her. There she asked me to sit on the bed and told Rajivto handle me carefully by winking her eye and left the room leaving both of us.
Now, the total room was calm for five minutes, but he broke the silence and asked me to stand, like an obedient student I obeyed to his words. He came from back & smelled my hair from top to bottom. Gently touched his nose to my ear lobes. I was feeling great and the sight of Rajiv’s dick came in my mind and was afraid of that going in my cunt. I told him please don’t do anything to me as I have to get married. He replied not to get tensed and this was a feeling to be enjoyed without fear. Also he assured that he will not touch me until she asks to do. I was relaxed & stood there silently. He went a little down & asked me to raise my hands & smelled my underarms, & told me that he was getting mad of that smell. He then asked me to remove my top and I refused as light was there. He then switched of f the light & put a dim bed lamp by which we were clearly visible to each other. He said it is essential to see each other’s private parts in sex as it increases the mood. Hesitantly I removed my top & stood with my slip on. He was really mad on seeing the hair in my underarms and started biting that & licking. He asked to remove the bottom & I followed. Now I was in my undies. He came down & smelled near my pussy. I can feel his nose tip touching my thing and was getting hot. Slowly inserted the tip of his tongue in to my navel and started rotating it. By that time my panty was wet with juices. He then removed his t-shirt & jeans. There was a lot of hair on his chest & a huge bulge in his underwear. He then opened his underwear and taken out his dick it was almost 8 inches.He asked me to touch it & I slowly I took it in my hand. It was very hot & the tip was leaking with some juices. He told me to suck it and I said no. He just smiled & came to me from back & unhooked my bra. Now my boobs were hanging., he had taken one boob in his mouth & started sucking it. I thought of asking about his word of not touching me, but remained silent in that pleasure.
He pressed my other boob & came down to my stomach, licked around there and again gone to my underarm. His dick was poking me in my stomach (due to the height difference). He then came to my neck and made wet all there. Took my face in to his hands and gave a slight kiss on my cheeks, meanwhile pressing my back ,I was in a different world & hugged him. Immediately he gave a long smooch on my lips and bit my lower lip, and taken my brown nipples in to his hands and squeezed them.He was moving his hands all my back and massaging my butt. He had separated them by inserting a finger into it. He then pulled me on to the bed & came on to me. By kissing me on my lips, chin, belly he went down and all of a sudden pulled my panty out. It was torn on one side and came out. I was shocked by this sudden incident. Slowly he went down towards my pussy. I felt some wetness already there and wanted him to go there, but Rajiv was eating & biting my pubic hair which was making me hot. He started chewing my hair & surrounding area was all wet by his saliva. By this time i was fully turned on and was offering him my sweet cunt by lifting my hip slightly up, so that his tongue can reach my pussy. He understood my situation and touched the centre line of my pussy with the tip of his tongue. I was like in heaven; this strange feeling of my cunt being sucked was really amazing & I was moaning loudly. He was squeezing my butt with both of his hands rubbing his fingers slightly on my ass crack. I hugged him tightly and pressed my bobs to his hairy chest.
By this, Rajiv understood that i am reaching my first orgasm and inserted his finger in my ass hole. Slowly he was moving in & out. It was paining me but still I was feeling a pleasure too. Suddenly the door was knocked & both of us got disturbed.
continued in the next part.
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Gay MaleMy heart was pounding in a symphonic surge as I lingered in front of the hotel room door. I checked and rechecked the metal plate bolted to the rich, dark oak. Number 2412. Yes, this was definitely the right room. The hallway corridor was empty. The dimly lit sconces glowed invitingly along the richly textured walls. They had led the way from the elevator of the lushly swank boutique hotel, The Hazelton, just like beacon lights leading me towards the precipice of a decision I still wasn’t sure...
Reluctance“I’m Brooklyn, and… whatever… I guess I’m a sex addict.” I glared at the group of pathetic faces in the circle surrounding me. This is so fucking lame. Why did I sign up for this? It was bad enough that I’d had to endure public humiliation when the scandal broke, but being away from the city in this touchy feely rehab centre set my nerves more on edge than they did to soothe them, which I’m sure was their original intention. From the moment I’d checked into The Belleview Retreat for Sexual...
AnalThe first shot struck Jennifer under the chin. That one came from Lawrence. She was still yelping when Trent’s delivery took her full in the face, filling her mouth and blinding her in an explosion of thick white. She spat and wiped her eyes clear, then pursued her boyfriend, scooping snow as she ran. Trent taunted as he fled, but stumbled knee-deep in a drift. “Bastard!” She laughed as she pelted him, then pushed him over while he was still off-balance. He pulled her with him and they rolled...
Group SexShe needed to have her senses challenged, to feel nature close to her; she didn’t want to hug-a-tree, she wanted the trees to hug her. Feeling more at home sitting on the wooden staircase than anywhere else, she observed the door that lead out into the front of the property. She stared, admiring the beauty of the oak grain, before raising her head to look up to the small window above the door frame. Before she arrived at her new home in a new state with her family, watching wispy clouds drift...
MasturbationThis is my real life story which started 2 years back when I got married to my beautiful wife Neha.She was 21 years and looked like 16 but she had full grown assets and almost nobody could spare a glance. The first 6 months was real first and we had an awesome sex life in spite of being a arranged marriage. She has been always shy to sexual things and I felt good in exposing that. Slowly we started fetish and BDSM to spice up our boring life. We bought lot of BDSM equipments as well in our...
Hello i am Aryan back with my second story. My First Story “RELATION WITH COUSIN SISTER”() was posted few days back.. Received many mails for that. Thank you for writing to me. If you want to write anything about that story also then write to me on my new mail id i.e. I just want to say that all the stories which i will post here are my true experience. I don’t have time to post fake or fantasy story here. Any girls or Bhabhi want to contact me for satisfaction or for chat then they can...
I escaped my fucked-up life into late-night erotic fantasies for years as waves crashed onto the sand beneath my balcony. I frequented my favorite site and started writing stories after becoming enamored with an author. Her stories had dirty, rough stuff I loved but also sensual and tender in a way I tried to emulate but couldn't master. I fantasized she spent hours getting aroused reading my words as I did hers. When she joined a new site, I quickly followed, seizing an opportunity to become...
Straight Sex“I’m Kylie, and I’m a sex addict.” I tried not to cry. It would have made things exponentially more embarrassing than just standing in front of the room telling a group of strangers that I was basically a sexual deviant. I bit down on my lower lip instead, producing just enough sharp discomfort to keep the girly tears back. I couldn’t believe I had really committed to this. Of course, I guess one could argue that I wasn’t very good with commitments, as it was. Ever since the depraved incident...
Group Sex“You’re such a whore, Shelby! But that’s still fucking hot…” Chelsie said as I briefly mentioned one particular aspect of my vacation to the Cayman Islands. “How were they? Big? Muscular? Come on, Shelby, details!” “Geez, let’s not be too demanding here. It was just sex on the beach with three incredibly hot guys! After all, I was on vacation…” I just stared at Chelsie, hoping she wouldn’t judge me for spilling the contents of my wild and dirty vacation. “Oh, please do tell! And you couldn’t...
Group SexChelsea was late, the victim of a failed alarm clock and cab shortage. She silently cursed her tight skirt and heels as she flew through the lobby, skidding across the polished marble floor just in time to catch the elevator. Breathless, she jumped in, glanced at her watch, and exhaled in relief. The button to the fifth floor was already glowing, pressed by the elevator’s only other occupant. When she turned to say good morning, the words stuck in her throat. It was Liam, the gorgeous new...
Group SexFor the first few weeks working at Joelle’s, my feet never really touched the floor. This was everything I had dreamed of, and more. In case you don’t know about her - though I’d be curious if you didn’t - Joelle’s the woman who turned makeup into a true art. Where others only “applied” lipstick, rouge and eye shadow, she painted with an artist’s skill and turned the plainest women into goddesses, into true artwork. Nobody knew her surname, and nobody needed to. All the big stars flocked to her...
SpankingAidan Black stared at the online text that flashed up onto the screen. ‘I luv ur stories!’ He yawned, and took another sip of his Jack Daniels. He quickly typed a reply and then leaned back in his chair. ‘What do you like about them?’ He smiled at the long pause. All these fans are the same, he thought to himself. Innocent young girls that dream of being treated like dirty sluts and too afraid to tell their college boyfriends that doggy-style after a long alcohol-fused pub crawl just wasn’t...
ReluctanceMelanie was a really attractive woman. In her early thirties, about five and a half feet tall. She was not slim, but very shapely with a very full ass, beautifully rounded, soft, shown off wonderfully in the tight skirts she loved to wear. Melanie had been part of our group for some time now, and Judy, my wife, and I had both enjoyed some pretty vigorous love-making with her at different times. She was one hot woman. There was just one problem – if you can call it a problem – she...
Hi readers, I’m Aman (name changed), a Southee, 25 years old currently working. This is my first sex story in ISS. Though I have been following ISS since 2010, I never had the will to submit a story of my own till now. So here’s my story :( will be different from typical cliché stories) It began at a very young age (I know this thing is not allowed but at that time I was not aware of the things I was doing, but believe me, all my entire life was influenced by the events that took place at that...
IncestGreetings to the readers of Indian sex stories. This is drex with his first story to add into ISS treasures. Hope you will like it.its a big story and you might find it slow but I request you to be patience… To began somewhere..I guess we all have someone in our lives who triggers the sexual desire inside us.. Well this story is about her with 10% of fiction(writer liberty as u may say).. The story goes back when I was 18 going to a wedding.. Was too excited cause I was going to meet my cousin...
Hi, I am sinner499 I am writing this story to share my experience with a really hot and sexy girl!! Something about myself I am 22 yr old guy not very muscular body as many would imagine I have a slim body and I have an 7″ long and fat cock. I live in Bangalore.Completed my engineering now doing training !! Now cumming to the story I was just one of those guys who thought that I could never get a gf. But time changes and I met this really beautiful girl in college! She was beautiful and just...
Two hours later, they had completed their lunch. Anjan and Arpita were joined back by Unmesh and Rahul and they had ordered some sumptuous food in the room itself. Arpita and Anjan both had a refreshing fuck at the bathroom, and were very hungry. And all of them ate heartily. Later Rahul and Anjan were at the living room, watching TV, while Unmesh took Arpita inside the bedroom. It was Unmesh’s turn as per the plan and he intended to use her well throughout the afternoon. Outside, Rahul and...
It had been five years since my wife died. I was stuck in a rut. It was as if my life had stalled the day Gina passed away. I was as emotionally healed as I would ever be, yet I lacked the will to go out and start anew. I worked, I came home. I slept, and then I headed back to work again the very next day. My life became a cycle. Rinse and repeat, ad infinitum.Maybe that’s why I allowed Christie to get so close to me. I told myself I just needed the help, but had I thought it through, I would...
TabooKailee knew she shouldn’t be here. He warned her of what would happen if she came into his space alone again. Shane, her father in-law was a good man, but he liked things his way. He wanted everything run his way. When Kailee and his son had to move back in with him and his wife while their place was being finished, the rules had been simple. Stay out of his office. Last week Kailee had been wandering around the large house, bored and looking for something to do. She walked down the hall and...
TabooI watched his plane lift off and disappear into the eastern sky. As I slowly walked across the airport terminal to the parking lot, I tried to compose myself as I wiped the last few tears from my cheeks. I could still feel his lips on my lips and the lingering scent of his shaving soap was still with me, but both sensations were rapidly vanishing. As I climbed into the car, I leaned back one last time saying good-bye to the man I loved. The feeling of the strength of his arms around me in our...
VoyeurAnna had only been living with Lincoln for three months, one week and five days when he walked in on her masturbating. He’d originally left with an overnight bag swinging from his clenched fist and a casual comment thrown over his shoulder to let her know he'd be spending the weekend at a friend’s place. Ten minutes after he'd walked out the door she'd stripped down to her tank top and panties, feeling the urgent need to relieve some of the tension that being around him regularly caused. In...
Straight SexDamon: I’ll bet you’ll get up to some trouble in Cabo. I smirked at the text that flashed up on our chat-log from the computer screen. He was always teasing me. Ashleigh: No trouble. At least not the good kind of trouble. I’m going with my boyfriend don’t forget. There was a pause, and while I anticipated his next words, I took a sip of the vodka soda I was prone to drinking while I spent my online hours chatting with my favorite virtual stranger, DamonX. I leaned back in my computer chair and...
TabooDedication: This story is just a bit of fun and is respectfully dedicated to all the tireless story checkers on Lush, whose hard work makes this site possible and who have to put with rubbish like this every day. Also, thanks must go to Fugly, whose story "Bag of Lush All Sorts" was the inspiration for this piece.I was in only my second month at Global Biofuels and still finding my way around the organisation. As the head of procurement in a modern, forward-thinking, ethical company, I had to...
TabooHello readers, I am back again after a long gap. I hope you had missed me and liked my previous stories in the meantime. If you have not, you can search with my name – xxxauthor, and I promise you will not be disappointed. This time too, I am back with an equally enthralling storyline, with the expectation that it will be liked and loved by a lot of you just like my previous stories. This story is about Arpita – a recently married housewife is her mid twenties, and how her ideal married life...
Robyn thought about sex a lot. She craved sex. Robyn wanted to feel a man’s strong masculine hands all over her naked body, to hear him whisper dirty words in her ear and make her pussy sopping wet.She imagined his hands pulling her hair back and his tongue in her ear as his thick hard cock penetrated her wet cunt. She wanted to feel his bulging biceps caress her sides and the feel of his sweat mixing with hers on their warm wet bodies.Just then Robyn looked up and saw bright red brake lights...
MILFAnal “You like that, don’t ya Fugs, hey?” asked Eric. “You like a big cock going deep in that sweet tight little puckered up ass?” “You know I do, Babe,” I said between thrusts. “But, do you want to talk or fuck?” “Oh, let’s talk please,” Eric smirked. “How was your day, sweetheart?” “Well asshole, it was going fine... until you opened your mouth. So, stop being a smart ass, shut up and”... BDSM “Take it like the bitch you are,” I said, as I rammed my condom covered rubber opaque cock...
Straight SexHi my dear ISS Friends, Hope you have enjoyed my last story “Sexperience in Chennai”. I am going to narrate what had happened after myself and Nandini came out of my bedroom into the hall.Those of you who are reading this story for the first time, please read the previous story for the continuation. As mentioned before only I was aware that Raagini and Abhirami were watching us copulating and after we came back from the shower the door was closed like normal and Nandini was not aware of the...