My Best Friend - University Years Ch. 03

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Our hero meets bi Naomi for her first cock experience.
8.8k words
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Part 3 of the 8 part series

Updated 06/11/2023
Created 07/17/2022
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My Best Friend: The University Years 3

Although the Christmas and New Year holidays were a fun filled and carefree period for me, I was raring to get back to University, and the first week in January saw me back at the small University city where I was studying.

As I came out of the railway station who should I find waiting for me, but my friend Alicia Sands, who seemed delighted to see me, and gave me a hug and a quick kiss on the cheek. Given our history as lovers, some people may wonder why it wasn't something a bit more passionate, but we were always aware that Alicia was married and a, 'respectable,' lawyer in the city, and so we always played down our connection in public. We went to a nearby coffee shop because she had something to tell me. She seemed very excited about it, whatever it was, and so a few minutes later we were at a table tucked away in the corner.

'Okay Alicia, what is it.' I began the conversation. She stirred her coffee, obviously thinking about what she was going to say, after all, she was a lawyer, and they rarely say anything unless they've thought it through first.

'Did I mention that I have a brother, an older one?' she added. I shook my head.

'No, no you didn't, but it somehow never came up in conversation while we were making love, so you've never mentioned it before,' I said jokingly. She smiled, but again she hesitated before continuing. I waited patiently, knowing she would get to the point one of these days.

'Oh well,' she said, 'you know now! I don't get on with him; he's a fair bit older than me, and absurdly religious, goes to church twice on a Sunday, that sort of thing. Anyway, at Christmas, it was almost impossible to avoid him, and all the family met up at his house on Christmas Eve. His wife is really nice, although totally under his spell, but his step-daughter Naomi, is another kettle of fish. She has a bit of spirit, individuality even, although she keeps it in check around him.

She's a lovely girl, very attractive, and we've always got on really well. I felt a bit sorry for her too, nineteen years old and having to live with my brother. My husband was going off on one of his business trips right after Christmas, and so I invited her over to stay the night once he had gone, so she could get away from the interminable preaching.

We have a spare bedroom, and my brother could hardly object, since the intent was to have a girly night at home, and not go out on the town.' I listened attentively, nodding at the right bits, but saying nothing, and she carried on with her story.

'A few days later, the 27th of December, she came over with a small overnight bag, and we had a nice time. After supper, I opened a bottle of white wine, and she confessed that she wasn't much of a drinker, rarely going out unless a family member was with her. She told me that she didn't quite, 'fit in,' with most of her acquaintances due to her up-bringing.

I sensed a bit of rebellion, and I poured her another glass of wine, which she tried to refuse, but it was too late, it was already in her glass. We chatted for ages, and she began to get a bit giggly. I suggested that we get into our nightclothes, and make ourselves comfortable, almost like a pyjama party, and we went to change. I was in the middle of changing when the phone rang; it was just my husband telling me he'd arrived safely and the hotel was fine, blah de blah.

Naomi knocked quietly at the door which was ajar, and I signalled her to come in. He spoke for a few more minutes, and eventually I got him off the phone. Naomi was sitting on the bed all this time, and I got the impression that she didn't quite know where to look with me being in rather skimpy underwear. As I looked in a drawer for pyjamas, not something I normally wear, she spoke.

"You have such lovely underwear," she said, and I thanked her for the compliment. "I always have to buy, 'granny knickers,' and, 'substantial,' bras. Nothing really nice and feminine like your lingerie," she went on. I found the pyjamas, and unhooked my bra, throwing it on the bed beside her. She picked it up and felt the material. "That's so soft, it feels really nice," she said, looking at me, or rather, my tits.

I pulled on the pyjama tops, slipping my panties off too, again throwing them on the bed, and again I noticed her watching me. Of course, as you know, I'm shaven, so there was no hiding place for me.'

'We're about the same size,' I offered, 'why don't you try on some of mine to see what it feels like.'

'Really? Oh I don't know, I couldn't,' but I persuaded her she could and took some of my nicest lingerie out of the drawer. I chose a killer set in black, almost sheer, and very, very skimpy. If she was going to wear nice lingerie, it might as well be damned sexy too. I also found a packet of unopened hold up black stockings to complete the ensemble.

She began to unbutton her pyjamas, and took off the top to reveal a really substantial bra, in beige. It looked really dull, like something my granny would have worn, and she had the good grace to blush. 'See, I told you. My mother always comes shopping with me and insists I wear stuff like this. It's horrible and I hate it, but nice lingerie is seen as frivolous and sinful. I'm getting really fed up of this religious crap,' she spat out. As she spoke, I unclasped her bra, and it fell away. She had really nice breasts and I told her so. She got all flustered then and blushed furiously, trying to cover herself with her hands.

'Don't be silly Naomi,' I told her. 'I've got breasts too, and yours are rather lovely. You've nothing to be ashamed of with those beauties.' She giggled nervously and blushed again. 'Besides, how are you going to put on this bra, if you don't take your hands away?' I reminded her. She reluctantly dropped her hands away, and I got a better chance to have a look at her.

She had such a lovely figure; it was a sin to hide it away in such awful underwear. She was about the same size as me, maybe even slightly bigger, and a lovely shape too. I held the bra in front of her and she put her hands through the straps, and I pulled them up to her shoulders. She turned away slightly, giving me the chance to fasten the back straps. She adjusted her breasts in the cups for comfort, and it was only when she looked down that she noticed the cups were totally see through, with her dark nipples plainly on view.

'Oh my,' she almost whispered, 'I'm nearly naked.' I smiled at her and kissed her cheek.

'Yes, but don't you look damned sexy? Absolutely sensational in fact,' I said, complimenting her. She blushed again, but I could see she was pleased. She untied the cord of her pyjamas and dropped them, stepping out, and I could see she had great legs too, shapely and slim. Her panties weren't quite as bad as the horror that was the bra, but almost. White and pretty much shapeless, they were definitely more suitable for the older woman. I held up the matching panties for the bra she was wearing, and her jaw dropped.

'Th... They're really small,' she stammered. I laughed and told her to get the old ones off, and still sitting on the bed, she slipped them down, showing a dark, untamed bush. I held out the new ones for her and she put her feet through the leg holes, and I pulled them up past her knees. She pulled them up the rest of the way herself, but they didn't look quite right, because her bush sprouted over the waist band and out of the leg holes, and she's dark, very dark. She stood up and looked at herself in the full-length mirror, and I could see her bottom lip trembling. She burst into tears.

'It's no use, I look a fright. The lingerie is lovely, it feels wonderful, but look at me - just look at me! I'm like some hairy ape, wearing the clothes of a princess,' she sobbed. I took her in my arms and gave her a comforting hug.

'Oh, you're not sweetheart, you're beautiful, but we just have to make a few changes and you'll be a princess too, I swear it.' And standing behind her, I slipped the panties down again. I had a feminine hair trimmer, for the exact place, and with her permission, I soon had her bush trimmed and trained. I even got her to open her legs a little so I could trim around her labia, and a fine set of labia she had to.

Her lips were quite substantial and as I worked around them I could see them glistening in the light. The vibration of the trimmers may have added to her wetness I thought. My innocent little friend was quite wet, which in turn made me realise I was wet too. When I was finished, I opened another drawer and taking a wash-cloth told her to go through to the bathroom and just wash, 'down there,' to get rid of all the loose hairs left after the trimming. She was back within minutes, smiling, but still modestly holding a hand over herself. This time when she put on the panties, she looked a million dollars. She positively beamed as she looked at herself in the mirror.

'Oh yes, that's more like it,' she said, turning this way and that. 'It's all a bit revealing though, isn't it?'

'Yes, that's the idea, and don't you think you look absolutely stunning?' I encouraged, adding, 'but we're not finished yet.' She'd never worn stockings before, so I suggested I help her put them on because one wrong move and they would probably, 'ladder.' She agreed and sat down on the edge of the bed. I got her to point her toes like a dancer and slipped the stocking carefully over her foot, and then up the expanse of the long, slim leg.

She began to tremble as I smoothed the stocking over her thigh, stroking high between her legs. By the time I had finished with the second stocking she was breathing heavily, and when the back of my hand 'accidentally' brushed against the crotch of the panties she gasped out loud. I pulled her to her feet, getting her to stand in front of the mirror again to see how sensational she looked. She nodded and smiled; I think quite overcome by her transformation.

'Oh, I'm so excited, I don't know what to do with myself,' she gasped out. Standing behind her, I pretended to adjust the straps of her bra, and she leaned back against me, the soft skin of her back rubbing against my titties. Tempted beyond any reason and very turned on myself, I reached round and cupped her breasts, gently squeezing her nipples, her eyes closed, and she moaned out loud, and I knew she was mine if I wanted to press home my advantage - and I did, squeezing and caressing, pinching her nipples.

I led her to the bed, and we sat down facing each other and then we were kissing. I pulled my pyjama top off, exposing my tits to her and she reached for them, tentative at first, but then as she became bolder, she gave them a right good handling. Her bra was soon off too, and we lay side by side on the bed, kissing and caressing. I pushed my knee between her thighs, and she worked her bottom back and forward, rubbing her pussy against my thigh. 'Oh god, I think I'm going to die of pleasure,' she moaned.'

'You must have touched yourself before Naomi?' I asked her quietly. She nodded vigorously.

'Yes, I have, but not very often,' she confessed, 'and never to completion. I've always been scared in case I made too much noise, with mum and dad in the next room maybe hearing me. When I found myself losing control I sort of nipped it in the bud. I always fantasised about being with a man, but this feels so good Alicia, please don't stop.'

' I slipped my hand under the waistband of her panties, and she opened her legs eager to be touched, and oh boy, did I touch her, and within minutes, she had her first orgasm, not just the first of the night, but her first ever. She proved to be very grateful and showed it in so many ways during the course of the night. Next day she was eager for more and I was delighted to give her more.

She's a quick learner and she just can't get enough, and that's where you come in. She wants a good hard cock in her and I hope you don't mind, but I kinda volunteered your services. She's a beautiful girl with lovely tits, and has a pussy that's just dying to be fucked, are you game?' I smiled at her.

'Yes, of course I am. Will you be there to assist, or do I meet her on her own?

'I thought if I was there to start with, just to make her hot and ready, to get her over the initial awkwardness, and then I could fade out of the picture, leaving her to your tender mercies. What do you think?' she asked scanning my face for reaction.

'Yes, sounds like a good idea to me. When do you think we might get it arranged?'

'I think I might be able to persuade her for tonight if you're up for it, or is that maybe too soon?' she suggested.

'No, the sooner the better as far as I'm concerned, but I'll drop my stuff off at my flat first, get a shower and something to eat, and meet round at your flat; say about 7.30pm, and if she chickens out, then we can have some fun anyway.' I smiled and squeezed her hand gently across the table, and so it was arranged.

I rang the doorbell promptly on 7.30pm, and heard the 'Clack, clack,' of Alicia's high heels on the wooden flooring. She opened the door, gave me a huge smile and hugged me tightly, whispering in my ear.

'I've been playing with her tits and pussy already - she's soaking wet and gagging for it. We're going to have some fun tonight baby,' she finished, and dragged me inside to introduce me to Naomi. She was everything Alicia promised, and more, a delightful young woman about my own age. There was a slight flush to her cheeks, but since Alicia had already told me she had been sampling Naomi's boobs and pussy before I arrived I wasn't surprised to see she had that lovely sexual glow. As Alicia introduced us I stepped right up to her and kissed her on both cheeks.

'Alicia told me you were lovely,' I said, 'and she wasn't telling any lies, you're gorgeous Naomi.' She blushed even more, but I could see she was pleased. Alicia suggested we all sit down and relax, so I sat on the couch beside Naomi, not too close, as I didn't want to spook her. I chatted to her for a moment or two while Alicia went into the kitchen to fetch me a drink.

It gave me a chance to have a more leisurely look at Naomi. She was wearing a white blouse, and I could tell she had no bra on. The blouse was just flimsy enough to reveal, yet conceal, but showing enough to be provocative. Her nipples looked quite delicious as they strained against the material, and her short skirt had ridden up to the point where I could just see the beginnings of her stocking tops. Alicia really had prepared her for seduction, and I was willing to bet that the lovely Naomi had already been stripped of her panties.

'Are you two getting on alright?' Alicia asked as she handed me my drink. I took a little sip and put it on the coffee table, and we both agreed that we were. Alicia took the initiative and went round behind the sofa, and hugged Naomi from behind. 'Naomi and I have been having a lot of fun since Christmas, and I've been teaching her a lot of new tricks, haven't I darling?' she said, smiling down at Naomi, who looked up at Alicia and nodded her head. Alicia kissed her then on the mouth, deeply and passionately and I heard Naomi give a little moan of pleasure.

As the kiss progressed, Alicia slipped her hands under the neckline of the blouse and began to massage and squeeze the fine young tits. While she massaged, she undid the buttons on the blouse, exposing Naomi's beautiful breasts to my view. Naomi moaned louder, but broke the kiss, saying quietly.

'Please, not in front of... ' and that was as far as she got because Alicia kissed her again, even more fiercely cutting off any protest that she had. I quickly slid across the couch right up close to Naomi, and while she was distracted with Alicia, slipped my hand up her skirt, right between her legs and felt her pussy, which was very, very wet.

She squealed in surprise, but it was much too late, as Alicia held on to her tightly, kissing her mouth and expertly fondling her tits which were now fully exposed. Naomi struggled a little, but quickly weakened under the twin assault on her most sensitive and erogenous zones, seeming to realise it was futile to resist and her legs opened wider to my touch, and I let my fingers penetrate her velvet depths massaging her g-spot.

The excitement was too much for her and she came within minutes, bucking and threshing about on the sofa as we manipulated her to a shattering orgasm. As she lay there on the sofa, slowly recovering, Alicia removed the blouse and I unzipped and pulled down the short black skirt, until Naomi lay completely naked and exposed to out appreciative view. She was absolutely stunning, but shyly curled up almost into a foetal position as she recovered enough to notice we were looking at her.

'C'mon sweetheart,' Alicia said, 'time for bed,' and pulling her to her feet ushered her into the bedroom. I followed and watched as they lay on top of the bed, Alicia still fully clothed, petting and caressing Naomi, who responded eagerly to her touch. After a few minutes Naomi was well on her way again, moaning and whimpering with each kiss, stroke and caress. I moved closer to the edge of the bed, and Alicia suggested I get my clothes off, and move in behind Naomi. I didn't need any encouragement, and joined them on the bed, snuggling into the back of Naomi, feeling her velvet smooth skin against my own. Alicia reached over and felt my cock; her hand wet from the juices flowing copiously from Naomi. 'Are you ready darling?' she asked Naomi, who nodded.

'Yes, but I'm frightened,' she admitted. Alicia reassured her, soothing her fears.

'Remember the first time we made love sweetheart, you were afraid then too, weren't you?' Alicia reminded her, and Naomi nodded. 'Well this is just like that time, only better. I'll stay with you and help you if you want. Would you like that?' Naomi nodded her head vigorously. 'Okay darling, just turn over on your back and spread those lovely legs as wide as you can, just for me,' she coaxed, and she did as she was asked.

I raised myself up and moved in between the long slim legs, now drawn up in a position to receive my cock. Her pussy glittered in the light, wetness oozing from between the open lips. Alicia then reached down and took my cock in her hand pulling me towards the expectant pussy. 'Let me do it,' she said quietly, and started to rub my swollen knob against Naomi's labia, covering it in the juices, and making Naomi moan and squirm at the same time. When my knob was thoroughly coated, she pulled me closer still, guiding me between the swollen labia. 'Push,' she urged, 'but gently, gently,' she cautioned, so I pushed gently, but Naomi, misunderstanding, pushed too.

'Oh god, it's too big, it'll never go in. Will it hurt?' she said, frantically looking at Alicia for reassurance, and then down at my cock for the first time. Her eyes opened wider with surprise or fear, I wasn't quite sure.

'Hush now baby,' Alicia calmed her. 'Trust me, just relax, and I swear you'll never forget this as long as you live. It may be slightly uncomfortable to start with, but once it's in, you'll feel like a real woman.' And all the time she spoke she rubbed my cock against Naomi's labia and clitoris, pulling me slightly deeper, until suddenly my knob was between the lips, pushing past the distended opening.

She looked at me saying, 'Okay, you're in, but be gentle and work it in slowly until she has the full length, but be gentle please, she's my baby.' I knew this was more for Naomi's benefit than mine, but I slowly withdrew and pushed, withdrew and pushed, her natural wetness aiding my entry.

Her hips began to push up towards me, telling me she was feeling only pleasure and wanted more, and now I was in her to the hilt, my balls gently grazing the skin of her soft, delectable arse. She became quite frantic as I stroked relentlessly in and out, with Alicia kissing her and fondling her breasts, whispering endearments into her ear, and occasionally reaching down between our bodies, stroking Naomi's clitoris.