True Life Conquests - Cover

True Life Conquests

Copyright© 2016 by hiddenrainbow

Chapter 6

True Sex Story: Chapter 6 - This series is a retelling of various sexual exploits I have had through my life. I have done my absolute best to record things faithfully, and base the dialogue on what I remember of the people involved (unless I have an email, a letter, video or whatever that records what they actually said). I have changed the names to protect myself, and also left out some details that might allow someone to figure out who people are otherwise.

Caution: This True Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Teenagers   Consensual   Heterosexual   True Story   First   Oral Sex   Anal Sex   Exhibitionism   Voyeurism  

My first day of university was madness. The campus was in near-central London, but the dorms were further out in East London. This was probably because it was impossible to get enough accommodation in central London to house all the students. Our dorm area consisted of a few mid-sized apartment buildings and a couple of houses. I was in one of the houses, which was all male. The house next to ours was all female, and I made a few friends there over the next few weeks. In the apartment buildings, the floors alternated male and female. The houses and apartments were busy with people all day. They were dragging boxes and suitcases around, losing keys, making new friends and saying goodbye to parents and family.

The day after everyone arrived, we had our first ‘Fresher’s Fortnight’ activity, a low-key tour of the campus during the day. When we reached the playing fields, I remember seeing a guy playing hockey (‘field hockey’ if you’re from North America) while holding a bottle of red wine. I thought ‘this is going to be intense’. I was right: it escalated quickly.

In our program, each first year student was assigned a student ‘parent’ from the year above to take care of them. The parent was always of the opposite sex, which to me seemed like a deliberate invitation to fornication. I suppose some students may still have been virgins (I know quite a few came from high school without having a year off as I had). Perhaps they felt it would be best to expose them to the opposite sex, as it were. We referred to these older students as our ‘mums’ or ‘dads’. I don’t think this was common to all programs, because when one of my housemates loudly declared ‘I had sex with my mum last night!’ in the cafeteria, he got a lot of strange looks.

Laura was my ‘mum’ and she was the president of the students’ association. I thought this meant that she would never be at parties and things, but that was a mistake on my part. Pretty much every student in the first and second years joined in Fresher’s Fortnight. It was two weeks of non-stop partying for everyone before the serious studying began.

Every night we’d go out to a different event, most of which involved drinking. Sometimes the drinking happened at a local pub in the East End, sometimes at the university bar, sometimes a club. Sometimes it was all three. There were fancy dress parties, foam parties, themed parties: Irish theme, American deep south theme, Hollywood theme, and Sherlock Holmes theme. Whatever possible excuse existed to get roaring drunk and make idiots of everyone. Many of the first years went all out on both the dressing up and the drinking, but the second years were typically more restrained, cynical observers of the ‘fun’.

At one of these parties, Laura introduced me to Tina, who was a friend of hers from second year. Tina had blonde curly hair, a pretty smile, and seemed to be very smart. She was about my height, which is tall for a girl, and about average build. We talked a lot that first night, she seemed happy that I wasn’t as focused on drinking as most of the first years. We exchanged numbers at the end of the night. Later that week we went for coffee at the campus cafe, but I was still getting adjusted so I didn’t see her again for a few nights. The next time I ran into her was what might have been the second last party of fresher’s fortnight.

This particular party was Braveheart themed, so all the guys dressed as Braveheart (blue facepaint, plastic sword and often a kilt). A lot of plastic swords got thrown onto the street or left on buses that night. Many of the girls had worn fancier dresses or kilts with tshirts, but quite a few, despairing of finding period costume on a student budget, had gone for non-period slutty. One of the girls from the house next to mine (her name was Naomi) was wearing black fishnets, black booty shorts and a black pushup bra, and nothing else. She was tall and pretty skinny, but looked amazing. I was finding it difficult not to stare.

I’d already made a good friend in my dorm building, whose name was Matt. His ‘mother’ was an Irish second year, I forget her name but she was a party animal. She was wearing what she insisted was an Irish kilt and a corset. She was also dragging us around the dance floor to meet all her friends, which was basically everyone. We’d been over to her house before the party and she’d helped us with our facepaint. As a result, against my will and better judgment, I had a blue cross painted on my face. I’d never even seen Braveheart, so I felt extra stupid.

I noticed Tina, who didn’t seem to be participating in the ridiculous dressing up that us first years were doing. She approached us, looked around at Matt and then at me. ‘Having fun?’ she said, grinning.

I rolled my eyes at her. ‘Of course, ‘ I said sarcastically.

‘Would you like to go somewhere else?’ she said.

‘Oh my god yes, ‘ I replied, relieved. ‘Anywhere.’

‘I think I might stay, ‘ said Matt, his eyes fixed in Naomi’s general direction.

‘Don’t stay out too late, ‘ I scolded him, wagging my finger. He shrugged and turned away.

‘So what’s the plan?’ I asked her.

Tina smiled at me. ‘Well we could go to the union bar, but it’s probably going to be busy. Do you want to come to my house?’

‘Sure, ‘ I said. I was slightly hesitant, for some reason Tina intimidated me a little. But it was preferable to staying here, where the obnoxious partying was already wearing thin.

We took the tube to Tina’s house; it was still running, as it wasn’t very late. On the way there, we talked about all kinds of things. She’d taken a year out after school and spent it working in Brazil. As a result she had a little trace of a Portuguese accent that was unusual for a white girl with blonde hair. She lived closer to campus in a small house with three other girls. Two were out and one was at home as she had an early start in the morning.

‘Would you like a glass of wine?’ she asked me in her kitchen.

I hesitated, because I’d already had quite a bit to drink, but I hadn’t got used to the idea of refusing alcohol yet. ‘Just a small one then.’

We drank our wine and chatted for a while, and then her roommate announced she was going to bed. ‘Do you want to go to bed too?’ Tina asked me.

‘Sure, ‘ I said. I wasn’t sure exactly what she meant, but I was getting tired.

‘We don’t have a spare room but you can sleep in my room.’ I followed her towards the stairs. At the top, she turned around and kissed me. It lasted for a long time, her tongue seemed to be actually exploring mine, caressing it, rather than fighting. She pulled away eventually and went into her room. ‘I’ll just go and get changed, ‘ she said. She took some clothes and left the room.

Tina’s room was large, but most of the space was floor. There was a dresser and a built-in wardrobe, and a single bed. That was mostly it. The dresser was white and ornate, and there were a lot of pink things on it. Pink bottles of perfume, photos in pink frames, pink hairbrushes. The bed was a white bed with pink sheets and blankets. I wasn’t sure what she expected, so I took a blanket and lay down under it on the floor.

Tina re-entered and laughed. She was wearing pink fluffy pyjamas and pink slippers. ‘What are you doing down there?’ she said. ‘You won’t be comfortable, just come into bed with me.’ She turned the light off and crossed over to the bed. She placed her slippers neatly next to the bed as she climbed in. ‘Come on!’ I protested feebly, but she insisted and soon we were squashed together in her small bed.

‘I’m glad there’s nobody else in here, or it might be a bit uncomfortable, ‘ I said. Tina grinned at me and started to kiss me again. After a couple of minutes, she started stroking my back and made her way down to my ass, which she squeezed unashamedly.

‘You’ve got a nice bum, ‘ she giggled. ‘Why don’t you take your clothes off, you’ll be uncomfortable for sleeping. Plus, now I think about it, I don’t know where you’ve been.’ I wriggled out of my clothes without moving too far from her. While we kissed, I kicked them out of the bed. Within a couple of minutes I was in only my boxers.

‘I feel naked, ‘ I said. ‘And you’re making me feel more naked’.

‘I’ve got a solution for that’, she said. ‘She reached down and pulled down my boxers under the covers. ‘There, now you don’t need to feel naked!’ She pulled them off and reached back around to stroke my cock, which was starting to get hard. ‘Mmm that is a nice one. Can I touch it?’

‘You’re already touching it!’ I said.

‘Thank you, ‘ she replied. She dropped my underwear over the side of the bed. I started to wonder if Tina wasn’t much smarter than I was.

She stroked my cock for a couple of minutes, then licked her palm and started to give me a real hand job. While she was doing this, she wriggled away from me a little (in the small bed it wasn’t possible to move far away). She pulled my hand wordlessly towards her pyjama pants. I slipped my own hand inside and immediately I could tell she wasn’t wearing underwear. Tina gasped as I made contact with her pussy. I continued moving my hand down, then slowly stroked my fingers back up, trailing the wetness of her pussy up her lips and over her clit. She began to work her hand up and down faster on my shaft. Soon it felt like we were battling to see who could get the other to cum first. There was no talking. The only sounds were the wet noises of her hand sliding up and down my lubricated shaft, my fingers rubbing her clit and dipping inside her pussy, and our combined soft moans in time with the other’s movements.

After a few minutes, Tina breathed ‘wait’. I stopped, and she squeezed my cock hard then slowly pulled her hand off. It felt almost like pulling slowly out of a wonderfully tight vagina, and I gasped. Tina rolled over, and I thought she’d cut me off and it was time to sleep. Then she pulled off her pyjama pants to reveal a round pale bottom. The covers had been pushed to the end of the bed; Tina pulled them back up over both of us then resumed her position facing away from me. ‘Come and cuddle me, ‘ she said.

I wasn’t sure if this wasn’t a mixed signal. Then again, an exposed pussy and a naked cock plus the word ‘cuddle’ seemed to suggest only one thing to me. To be completely certain, I moved up close to her and spooned her. My hips were in the right position to thrust into her, but my cock was pressed against the softness of her bottom. For the moment, I was in no danger of ‘accidentally’ penetrating her.

‘That feels nice, ‘ sighed Tina. She wriggled a little, as if to get comfortable, but continued subtly rotating her hips. This rubbed her soft bottom against my stiff cock. ‘Maybe you should move down a little bit, ‘ she said after a minute or two. There was a smell of arousal in the air that suggested I’d be inside her soon.

I’m not sure why, maybe it was a response to her natural sarcasm, maybe I wondered what would happen, but I decided to offer some resistance. ‘I think I’m comfortable here, ‘ I replied.

There was a pause before Tina said ‘are you sure?’

Ah, I thought, she knows exactly what she wants but she doesn’t want to ask for it. ‘Mmhm, it’s lovely and warm here.’

Tina paused again. ‘Well I don’t think it’s good to get too comfortable, maybe you should be down on the floor, ‘ Tina said.

‘Sure, if you’d prefer that.’ I said. I don’t think she had expected me to call her bluff on that, but part of me got the impression that this was a game; that everything this girl did was a game.

‘It’s a bit cold down there, it’s much warmer in here though.’

I leaned over to her ear and whispered ‘In where?’

She shivered a little and turned a little towards me ‘In the bed.’

‘Is that really what you meant?’ I moved down a little, rubbing the head of my cock against her bottom as I did so. She seemed to be losing her cool a little.

‘I ... yes. Mhm.’

‘I don’t think it is, ‘ I said. I was now positioned with my cock resting up against her pussy. I could feel the wetness on my tip, and my feet were poking out of the end of the covers. ‘What did you really mean?’

‘I don’t know, ‘ she said breathlessly. Now I felt completely in control. Whether it was the alcohol, or the thought of somehow conquering this clever woman I didn’t know; I wanted her to beg.

‘Perhaps I should take the floor then, ‘ I sighed and started to slide further down the bed, making sure to rub my now wet cock head against the backs of her thighs. Tina moaned. ‘Since you don’t know’.

‘No ... I.’ She faltered, and I stopped moving down the bed.

‘What did you really mean?’ I said patiently. I put my hand on her hip and squeezed a little.

‘I meant in me, ‘ Tina said in a quiet voice.

‘In you where?’ I replied. I started to wriggle back up the bed again.

‘Inside me.’

‘Inside you where?’ I said again. I held my cockhead against her pussy lips again. This time I slowly rubbed it back and forth until it was slick with her fluids. I could feel the slight tickle from her pubic hair against me.

‘In my cunt, ‘ she gasped. ‘I meant it was warm in my cunt.’

‘Good.’ I said. I paused again. ‘So is there something you want to ask me?’

‘Can you put it in me?’ She whispered.

‘Not quite good enough, ‘ I replied, continuing to rub myself against her. ‘Try again.’

‘Can you put your dick inside me?’ Tina was breathing harder and having difficulty speaking.

‘I can, but I won’t. Not unless you say please, ‘ I whispered in her ear.

‘Please, ‘ she moaned. ‘Please please please put it in me now.’

As she reached the last word I pushed my hips up, sliding my cock into her with a less than romantic queefing noise. She was extremely wet. I wasn’t pushed up in her all the way, but she shuddered and whimpered as if she was full up to the eyes. I moved my head back to her ear to whisper to her. Doing this pushed my cock further inside her and she made a sound that could have been a moan or a groan of pain.

‘Since it’s your bed I’ll let you do the moving, ‘ I said to her. I leaned back a little and lay my head down, without moving my hips. I was still buried inside Tina but not doing anything about it.

Tina wriggled from side to side with some difficulty, making a disappointed whining noise, as this didn’t seem to do much. I maintained my position. Tina reached her arms above her head and pushed against the wall. I stayed where I was but she slid down further onto my cock until it was fully inside her. ‘Oh shit, ‘ she gasped. ‘Ok I can do this’. She wasn’t referring to fitting my cock inside her, but somehow moving herself to extract some pleasure from it. She grabbed the edge of the bed and pulled herself back up, then used one hand to push herself off the wall again. Clumsily, she managed to fuck herself with my cock for a short while like this, but then maybe her arms got tired. She moaned and dropped them by her sides.

‘Do you want to cum?’ I said to her.

‘Mhm. So much. I’m pretty close but I can’t do it this way.’ There was a pleading tone to her voice.

I put my arm around her and rolled onto my back, ending up with Tina on top of me but facing away. This also pulled her fully onto my cock. I had a strong temptation to thrust up into her over and over until I came, but I managed to resist in favour of continuing to tease her. ‘Your move, ‘ I said.

Tina stayed facing the other way, and began to slowly move up and down on me. This too seemed to be a little awkward for her, but it didn’t stop her from fucking herself faster and harder. After a minute or two, she started shaking and quietly groaning. She stopped thrusting to fall forward a little, her hands on my legs, her own body quivering with her orgasm. I got a lovely view of her scrunched up pink anus as she came, her pussy contracting around me.

After she stopped cumming, Tina turned around somewhat awkwardly, keeping my cock inside her so she was now riding on top and facing me. ‘I want you to keep going until you cum, ‘ she said.

Perhaps it was her telling me what she wanted; perhaps it was the high I got from being in control myself. At that moment, to me the control was more important even than my own pleasure. ‘Maybe next time, ‘ I said.

Tina looked a bit surprised, then just unhappy. ‘You don’t want to?’

‘Later, ‘ I replied. ‘In the morning if you’re lucky.’

Tina slid off me, which itself felt pretty amazing. I had a moment of regret that I hadn’t simply used her until I came, then I was out of her and the feeling was gone.

In the morning, Tina had to leave early to get to class, and I had to get back to the dorms to change my clothes. It may have been my very first ‘walk of shame’. Tina called me later, but I didn’t answer. Being able to make this smart girl want me so badly was a bigger turnon for me than actually having her do the things she wanted to do. This was the first time I considered myself a bit kinky, because I knew thinking that way was backward.

After a few days Tina and I hooked up again. This time she came round to my dorm. She met me outside the building, which caused a few comments later because it was an all-boys building and we weren’t supposed to have girls in our rooms. I took her up to my room. As soon as we were through the door she stripped her clothes off, despite the fact that my blinds weren’t closed. Anyone in the playing field outside could have seen her naked. I left the window open and let her lean over my desk while I fucked her from behind. Afterwards, she leaned out of the window naked and watched some kids playing football on the field. None of them ever noticed her.

Over the next few weeks, I fucked Tina a few more times. We delved a little more into control and denial. It seemed to turn her on because she really wanted me, and turned me on even more. It wasn’t meant to be though. For reasons that I won’t go into, university didn’t work out for me. I ended up dropping out of school and going back home. Tina was very sad that I was leaving, and promised to come and visit me once school finished for the year. I still wonder if leaving was the right thing, and what could have happened with Tina (and school) if I’d stayed. She was never my actual girlfriend, but she could have been one of the best.

When I got back home, I wasn’t sure what to do. To kill some time, I picked up a job working in the bar of a nearby hotel. Hotel bars are great places to work if you have to be doing bar work. People often give crazy tips and it’s rarely super busy (except when there’s a big event like a wedding). I learned how to make some good cocktails, although most of the regular customers were old men who came in to drink expensive whisky and smoke huge cigars.

One of the good points of working in the hotel was that most of the staff there were young. My boss was about 25, and his boss, Lee, was only a few years older. Lee was a coke addict, and more interested in stealing money from the hotel to fuel his coke habit than in his employees. His ‘system’ was to take some money out of the till at the end of the night. He would destroy the receipts for that money, then put something in the breakages book that would explain why that amount of booze was missing. According to my boss he was making a lot.

The upshot of all this for the bar staff was that we could pretty well do what we liked. Sometimes my boss wandered off, leaving me completely alone and getting paid for doing nothing. Sometimes we’d make cocktails for each other to try. One night he ended up getting one of the front desk staff to give him a free room because he was too drunk to drive home.

During the day the bar was very quiet, so I usually worked some time in the cafe, which was in the lobby close to the bar. Being in the lobby meant a constant flow of customers, and it was exhausting. The cafe sold a several different coffee drinks that I had to learn to make, and various pastries and cakes. Mostly the people who worked in the cafe were pretty girls, it being that sort of job. Helen was the only one I talked to much. She was short, although ‘petite’ is probably a better word, and had very long blonde hair that she obviously spent a lot of time on. She was pretty, although I noticed that she tried to not open her mouth too wide when she talked or laughed, because she had a crooked tooth on one side. The hotel uniform for the girls included a yellow shirt, yellow tights and a grey skirt, which the hotel provided. One of the first things Helen told me was that she had surreptitiously shortened her skirt, and after doing so her tips had doubled. This didn’t surprise me, I was sure all the middle aged businessmen loved ogling her.

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