Higher Education Ch. 03
Chapter 13: Jackie to the rescue
The next day I tried to find Safia but there was no answer when I knocked on her door and she did not respond to my calls and texts. A girl in her corridor said she thought she had gone home for a few days. I was miserable and didn't know what to do. I hated to think that Safia thought badly of me and I dreaded the thought that this might be the end of our relationship. That evening I moped around the house and continued to do so for the rest of the week. I skulked in my room trying to do some work but not succeeding. I continued to text Safia with no response.
One evening a few days later Jackie knocked on my door.
"Do you fancy sharing a bottle of wine," she asked.
"Not really I am a bit tired," I replied.
"It's only seven o'clock," Jackie responded, "and you have hardly been out for days. Come and tell me what's going on."
Eventually I was persuaded to join her on the living room couch where she thrust a large glass of red plonk into my hand. Initially I was too ashamed to confess what was upsetting me but Jackie skilfully wheedled the full story out of me.
"So she just kicked you out? But why?" Jackie asked after I had told most of my sorry tale.
"She said I had raped her," I finally admitted.
"You raped her!" Jackie was aghast. "That doesn't sound like you David."
"Well I didn't exactly rape her, I just didn't stop when she wanted me to."
"Go on tell me how it went."
"Well she said she had a present for me and then she made it clear that she was going to do something well.... sexual for me as a sort of present," I explained.
"What sort of thing?" Jackie asked.
"Well she actually suggested that we have anal sex. You know she's a Muslim and wants to preserve her virginity and all that but she said you know.... That I could fuck her like that." I went on.
"So what kind of lubricant did you use?"
"Lubricant?"
"Yes surely you used something to make it a bit easier for the poor girl." Jackie said incredulously.
"Well I sort of used a bit of saliva and then just pushed it in," I confessed.
"And then I suppose you just thrust away into the poor girl?" Jackie suggested.
"Well yes, I thought that was what she wanted and well.... I hadn't had it for weeks. I suppose I was a bit desperate. Oh God Jackie, have I been a complete idiot?" I asked.
"Well basically yes," Jackie responded. "You broke the first three rules of anal sex."
"What are those?"
"Well first make sure the lady is completely ready, second use lots and lots of lubricant and then some more and third go real slowly to start with."
"Oh Christ, I didn't do any of those," I replied. "No wonder she freaked out. But hey when I went to that party with you, you know I went to the anal room and did it with Lady Melksham."
"Yes"
"Well it was fine then, I mean I just slipped into her and didn't use any lube," I went on.
"But David remember Lady Melksham is an old hand not a nervous young virgin like Safia and she had probably been buggered several times that night so her arse would have been well and truly stretched and lubricated. No wonder you just slipped into her," Jackie explained.
"Oh God," I groaned, "I never thought of that. I have really fucked up haven't I?"
"Well maybe not," Jackie said reassuringly, "you might still win her back. Even if you don't I think you should learn how to do anal with a lady properly."
"Well there's not much chance of that at the moment," I replied miserably.
"Not necessarily," Jackie said. "After all I could teach you."
"What you mean you would... you know, let me?" I said in amazement.
"Well why not, what are landladies for?" she replied.
"Well I don't know many that would let you do that to them," I said, cheering up for the first time in days.
Somewhat later that evening Jackie and I had started on the second bottle of red and my lesson was in full flow. Jackie was naked, bent over the seat of the sofa resting her elbows on the cushions. I had just finished licking her pussy until her juices were flowing strongly. My weeks of practice in that department with Safia seemed to have paid off and she complimented me on my muff diving skills. Now Jackie had insisted that I use my tongue on her nether hole. I was a little hesitant, a woman's arse seemed a little dirty to dip one's tongue into.
I paused looking down at the two plump globes of Jackie's arse, I gently separated the twin hillocks and there peeking up at me I saw her delicious rosebud close up for the first time. My cock stiffened perceptibly. I wanted to fuck that tight little starburst so badly. Gently I leant forward and tentatively licked around the tight entrance. Jackie murmured encouragement and I licked more cautiously, circling the wrinkled sphincter. I experimentally pushed my tongue inward a little and found I made little headway. I licked around the entrance some more and I could feel Jackie relaxing. Experimentally I brought one hand forward and caressed her pussy. Again she murmured her appreciation and I brushed her clit, continuing to rim her anus with my tongue. I tried once more to push the tip of my tongue inward and this time just managed to probe inside a little. The taste was fine and I pushed a little further gently tongue fucking the tight entrance.
"Oh David, you have no idea how good that feels," Jackie murmured. "Please don't stop."
I had no intention of doing so and continued to rim her arse while gently fondling her clit and occasionally pushing a couple of fingers deep inside her sopping pussy.
"Now David how about some lube in there to really open things up," Jackie suggested.
I reached for the bottle of lube which Jackie had left on the coffee table. I wasn't too sure how much to use or how to apply it but I squeezed a little onto my finger and circled her tight rosebud.
"That's it," said Jackie encouragingly "push it in and spread it inside."
I gently pushed by index finger against her tight hole and slowly eased it inward. Certainly the lube made things easier and once past the initial resistance I was able to slide my pinky around in her back passage easily. I decided to take Jackie at her word about using more lube than you thought necessary and put another generous amount on my finger. It slid in even easier this time and I gently eased it to and for ensuring her whole passage was well coated. I tried experimenting with two fingers and plenty more lube. It was harder to stretch Jackie's anus to accommodate them but with some gently probing I slowly worked both digits into her rectum. I could feel her sphincter relaxing and stretching. This is what I should have done with Safia. No wonder she had freaked out. After a few minutes of gently thrusting and probing Jackie announced that she was ready.
"David I think I am ready, are you going to put your cock in my arse,"
"Of course if you are ready," I responded.
I began to generously coat my now throbbing cock with lube. I could not wait to feel Jackie's plump bottom tightly gripping my pole but I didn't want to hurry things along too much and spoil everything again. I positioned the purple mushroom of my cockhead against her brown hole and paused.
"Nice and slow now," urged Jackie. "Just press firmly but not too hard until you feel things giving way and then slowly push in but not all the way at once."
I pressed inward a little with no effect. I thrust a little more firmly and just managed to get the tip of my cock into her entrance. I began to infitessimally ease my cock forward pausing each time I pressed forward another half inch. The pleasure was exquisite as I felt the tightness of her sphincter slowly engulfing my prick.
"Is that alright, I am not going too fast," I asked.
"No that's delicious," Jackie responded. "Just keep going real slow like you are now."
Bit by bit my cock sank deeper and deeper into her rectum. I paused and looked down. The view was delectable. The twin peaches of Jackie's rounded posterior framed the vision of the tightly stretched circle of her anus the centre, which was tightly stuffed with my swollen pole. I desperately wanted to fuck her senseless but knew I had to restrain myself. I continued to thrust forward until finally my prick was buried to the hilt in her luscious arse. I paused enjoying the delicious sensations of the base of my cock being tightly gripped by her sphincter and her soft buttocks caressing my hips.
"Now you can start thrusting but very slowly to start off with," instructed Jackie. "And if I say stop you stop immediately."
I murmured my agreement and began to tentatively make tiny movements in her arse. The sensation was exquisite and quite unlike fucking a vagina. For a start her arsehole was far tighter than a pussy but also the pressure was all around the base of my prick whereas it seemed the main stimulation in a pussy was around the cockhead. I immediately decided that I adored anal sex and wondered if I would ever again persuade Safia to allow me to do it with her. This thought soon faded as I became lost in the delight of fucking Jackie's plump arse. After a few minutes of cautious and gentle movement she encouraged me to go a little faster and I began to thrust in and out rather more deeply.
"Oh Jackie, I can't tell you how amazing this feels. Are you sure it is OK for you?" I asked.
"It's always a little painful at first but not much as you were so gentle and now I am really getting in to it," Jackie replied. "I could just do with a little attention to my clit do you think you could manage that?"
I reached forward, it wasn't all that easy to reach Jackie's clitoris while fucking her from behind but I soon found the swelling little bud and began to gently rub it as a slowly thrust back and forth in her back passage.
"Oh yes that's the spot, keep on like that," urged Jackie.
It felt wonderful not only to enjoy the exquisite pleasure of Jackie's beautiful bottom but to know that she was enjoying it as much as me. If only I could achieve this with my darling Safia. Soon Jackie's pussy was leaking copious amounts of juices and I used these to anoint her clit. I could sense she wanted me to rub her harder and began to swiftly massage her as my strokes became ever longer in a firmer in her tight sphincter.
"Oh don't stop now my arse is on fire but I am so close to coming," gasped Jackie.
"Do you want some more lube?" I asked.
"No I am so close, just fill me with your big fat cock," she responded
"Oh your tiny arse feels so tight around my prick," I added.
"Oh I want to feel your hot spunk squirting up my dirty little hole," she groaned.
I had never experienced a woman talking dirty like this but I could see she was getting turned on by it and it was getting to me as well.
"Oh yes Jackie, I am going to fill your arse with my sperm, my cock is going to burst," I added.
"Oh fuck me, fuck me harder. Stretch my little hole so wide," she cried.
I was now pistoning away in her backside. I was sure it must be painful but Jackie just kept on encouraging me and I sensed she was close to coming as her cries reached a crescendo and then she was simply screaming "yes, yes, yes" over and over and I pumped her anus mercilessly until I felt a tightening sensation in my scrotum and tingling in my balls. Then my prick simply exploded and with a whoosh I had the most almighty ejaculation. I could feel the come spurting from my cock over and over again with each thrust until I had milked my balls dry and my penis dropped from Jackie's reddened and well fucked hole.
Afterwards we helped one another to clean up with a box of tissues and Jackie brought us a couple of glasses of scotch to celebrate.
"Well I know that you lost your anal virginity with Lady Melksham but I think tonight is the night you really got initiated into anal sex and you passed with flying colours," said Jackie.
"Do you really mean that?" I asked in surprise.
"Of course, that was a great fuck," Jackie replied. "Though remember that if you do it with a girl and it's her first time you may need to be a lot gentler but you did good.
I lay back not only enjoying the afterglow of my second successful anal coitus but also basking in Jackie's generous praise. It boosted my dented confidence after the fiasco with Safia and I at last felt that I might have a chance if not with her then maybe with some other girl.
Chapter 14: A trip to London
It was about a couple of weeks after my night with Jackie that I decided to take a trip to London one Saturday. I had read in the paper that there was an exhibition of Turner's work at the National Gallery. He was one of my favourite painters but I had only managed to see a few of his pictures in different galleries which I had visited over the years. Unfortunately none of my university friends seemed the slightest interested in art so I decided to make an expedition on my own. I excitedly boarded the train with my cut price student rail ticket and was soon in London.
The exhibition proved to be every bit as wonderful as I hoped. Some of the paintings such as 'Rain, Steam and Speed' of the Great Western Railway and the steam boat in a snow storm seemed to prefigure impressionism while the vast canvas of 'The Fighting Temeraire' with its vivid sunset colours blew me away at the end of the exhibition. I was just standing there in awe admiring this wonderful masterpiece when I heard a voice behind me.
"Hello, stranger. Fancy seeing you here!"
I turned around and was surprised to find myself face to face with Sarah who I had encountered at Lord and Lady Melksham's orgy.
"Sarah, how lovely to see you," I exclaimed. "I just came to see the Turners. Aren't they amazing."
"Oh wow do you love him too?" enthused Sarah. "He has got to be my favourite painter. Isn't this just the most brilliant picture?"
We spent a few minutes sharing our views on the exhibition and then I suggested we repair to the café for some lunch. Over tea and sandwiches we quickly caught up on one another's lives since our first encounter. Sarah it seemed was studying history of art at the Courtauld and actually doing her doctorate on Turner. She asked if I would like one last look at the Turners so after lunch she showed me some of her favourite pictures and explained some of the finer points of Turner's technique. As a fellow fan I found all this fascinating and before we knew it a couple of hours had passed.
Sarah looked slightly less chubby than the last time I had seen her but she still had the same unruly mop of curly reddish blonde hair and the same cheeky smile which I had found so attractive before. She might have lost a few pounds but she had managed to keep her great curves and as I followed her into the café I couldn't help noticing how well her bottom filled her tight pair of jeans.
"Hey I am not keeping you?" she suddenly asked. "I mean have you got to go anywhere else or meet anyone?"
"Erm no," I replied. "I mean I was just going to get the train back home."
"Oh well, do so if you want to but I was thinking of getting some food and cooking for myself tonight as my flatmates are away. You would be welcome to come and join me," Sarah suggested.
"I would just need to check what time the last train goes but that sounds great,"I replied.
"Well of course if you need to get back tonight, but if you want to stay over we have loads of room at the flat," Sarah said with a cheeky grin.
I wasn't too sure exactly what Sarah was suggesting but even a meal and a bottle of wine with her would be pleasant if that was all that was on offer and given our history I hoped it might be something more.
We took the tube out to the suburb where Sarah had her flat and she led me to a nearby supermarket. She rapidly piled ingredients into her basket then I insisted on buying a couple of bottles of wine. I pulled down a bottle of white burgundy and began looking at the blurb on the label.
"You like white burgundy?" Sarah asked.
"Oh yeah," I said. "I don't actually know much about wine but Jackie got me into this."
"One of my favourites too and should go beautifully with the chicken I am going to cook," she replied.
Sarah lived in a large flat which she shared with three other girls. When we arrived she quickly made some tea and we settled on the sofa in the shared living room for a chat, catching up on what had happened since our first encounter. Sarah, it seemed, had had a short lived relationship with another postgraduate student but she had recently dumped him and she was single again. She said that she rarely saw Caroline who I had also met at the Melksham's orgy. She was working abroad much of the time but occasionally went for a drink with Sarah when she was in London. Sarah was keen to know about my love life so I explained that I had embarked on a relationship with a gorgeous Muslim girl who was a fellow student but things had not worked out.
"So was her religion the problem which led to the end of the relationship?" asked Sarah.
"Well not exactly, if anything it was my fault," I explained.
"Oh God, you didn't cheat on her," exclaimed Sarah. "That's why I dumped my bastard ex."
"Oh erm no, nothing like that," I stammerered.
"Oh come on David spill the beans," urged Sarah.
"Well how can I put it. I wanted to take things a bit faster sexually than she did," I said.
"Oh so you wanted to fuck her and she wouldn't let you because she was Muslim and so you dumped her" said Sarah in her direct way.
"Well not exactly," I replied. "It was actually she who dumped me."
"Look it's none of my business if you don't want to talk about it," responded Sarah sensing my discomfort.
"No it's OK, it's just a little embarrassing," I explained.
"In what way?" asked Sarah, still obviously eager to know more.
"Well erm she didn't want to lose her virginity on account of being Muslim and everything but she said she wanted to try anal, you know because she would still technically be a virgin." I reluctantly revealed.
"So didn't she like anal sex after all?" replied Sarah, her eyes lighting up with curiosity.
"Well I think I was a bit too rough and she wanted me to stop and I didn't," I admitted. "I mean I didn't intend to hurt her and I am really ashamed and everything."
I realised how lame this sounded and wondered whether Sarah was going to kick me out in disgust.
"So you really like the idea of anal sex but never managed to do it properly," Sarah said.
"To tell the truth I have done it a couple of times," I explained. "At the orgy, after we got separated, I found my way to the anal annexe and Lady Melksham let me fuck her... you know up the bum."
"Oh wow, I never managed to get down there. That would have been a sight to see you shagging old Lady Melksham up the arse. Did you like it?"
"It was amazing," I replied. "The trouble was I just assumed that I could do it the same with any woman. When Safia suggested it I never thought that with her being a virgin and all I might have to approach things..... well a bit differently."
"So you didn't really rape her you just went in a bit too forcefully,"said Sarah.
"I suppose so," I replied. "But I still feel bad that I upset her."
"You said that you had had anal a couple of times when was the other time?" asked Sarah still curious.
"Oh that was with Jackie," I explained.
"What Jackie your landlady who brought you to the Melkshams?" Sarah asked.
"Yes of course," I said.
"What, was this before or after you had tried to fuck your Muslim girl?" Sarah queried.
"Oh after," I explained. "When Jackie found out what had happened with Safia she said I ought to learn how to do anal properly and gave me a lesson."
"My god she sounds like the perfect landlady, taking you to orgies and giving you lessons in anal sex!"
"Oh she's great, I am so lucky I got to stay with her," I admitted.
"So it sounds like you are really into this anal sex thing," said Sarah.
"Well in a way yes, though doing it the normal way is pretty amazing too," I replied.
"I think you wanted to fuck me in the arse at the orgy didn't you," Sarah said continuing her interrogation.
"Well erm yes. I wouldn't have minded, though it was amazing anyway." I swiftly added.
For a moment there was an awkward pause in the conversation then it was my turn to satisfy my curiosity.
"So Sarah, you seem awfully interested in anal sex. Is it something you are really into?"
"Oh well I am just curious about it," she replied suddenly on the defensive.
"What you have never actually done it?" I asked.
"To tell the truth no," she admitted. "I was actually quite keen at the orgy but kind of chickened out of going down to the Anal Annexe."
"And what about this boyfriend you dumped. Didn't you think about trying it with him?" I asked.
"Well I actually suggested it to him but it kind of grossed him out and then he kind of lost interest and that's when he cheated on me with that other bitch."
"Hey I am sorry to hear that," I said. "But he must be crazy passing up the offer of anal with a girl like you."
"That sound a bit like a proposition," said Sarah.
"Well may be it is," I replied. "I really like you Sarah and I fancied you from the moment I first saw you at the orgy and I think you have the most gorgeous bum."
"Well I will take that as a compliment, though personally I think it is far too big," she responded.
Suddenly Sarah seemed to need to change the subject and stood up.
"Hey look at the time, I am starving," she announced. "Want to help me get dinner ready in the kitchen?"
I followed her into the small galley kitchen. There wasn't much room to move. She set me to work chopping some vegetables while she got busy sorting out the chicken. For a few minutes we worked away busily with our back to one another. I had just finished my chopping and turned around to tip the veggies into the casserole at the same moment as Sarah turned and reached across me to open the fridge. She stumbled and nearly tripped over but I caught her round the waist and stopped her; for a moment she was there with my arms around her, her face inches from mine. For the first time I could see her unusual green eyes flecked with hazel close up and her pink lips curved into a curious smile. Suddenly I could no longer hold back and kissed her gently on the mouth. She responded by kissing me back more firmly. Soon our lips were locked together in a long passionate snog.
We carried on kissing for what seemed like ages then Sarah began to unbutton my shirt. Her fingers traced across my chest and gently stroked my nipples. I could feel myself getting more and more aroused. I pulled at her tee shirt and briefly, breaking off from kissing her, pulled it over her head. Underneath she wore a simple cotton bra with her magnificent tits spilling out over the top. I reached for the strap and after a moment of awkwardness managed to undo the clip. She shrugged off the bra. Her breasts were huge, surmounted by magnificent pink nipples I could not resist bending and nibbling one and then sucking at first gently and then more firmly on one of her hardening teats.
"Oh David I love having my tits sucked," gasped Sarah, so I continued my suckling.
After a few minutes of enjoying her mammoth mammaries, she suggested we move to the bedroom.
"There's not a lot of space in here let's move to my bed," she demanded.
We were soon naked and stretched out on her quilt. I was delighted to discover that Sarah did not shave and had a wonderful tuft of reddish pubes sprouting from her cunt. As we kissed and fondled one another on the bed, Sarah's hand reached for my by now erect prick and began to rub it softly.
"Oh god you are lovely and hard, do you want to fuck?" she asked.
"Well only if you are ready. Don't you want to you know get prepared a bit first?" I asked, assuming that some foreplay might be in order.
"Hell no, it's about six months since I had a good fuck. I want you so badly David, so let's just get on with it," Sarah explained.
I needed no further encouragement and as Sarah spread her plump thighs I positioned my rampant tool at the mouth of her gaping pussy. Tentatively I pushed forward feeling the slick walls of her vagina enclose the tip of my prick. There was that exquisite first moment when a woman's cunt enfolds your cock. I paused, about half my cock in her slit enjoying that sensation and then I quickly slid the whole length into her, one more pausing to enjoy the feeling.
"Please fuck me, I am so horny," demanded Sarah.
I began to comply with her demand, slowly thrusting my tool in and out of her gushing passage.
"Oh my god I need that, don't stop, your cock feels so good.
I began to thrust faster and faster with no finesse or technique. This was just plain simple rutting as my cock pistoned between her thighs. Now Sarah began to pant and emit tiny cries as I impaled her over and over. Her head was back on her pillow her mouth gasping in ecstasy while her two magnificent breasts jiggled on her chest in time to my thrusts. I felt the softness of her tit flesh, mauling those magnificent bosoms. I craved release but held back, knowing that Sarah was close to her own climax.
"Oh David, don't stop, don't come yet, I am so close," gasped Sarah.
I was by now hammering away at her pussy, which was superbly lubricated by her ample juices.
"Oh god, Oh god," Sarah began to moan, her cries becoming increasingly incoherent reducing to small screams each time if thrust into her.
Then, "Oooh yeeeees!" she screamed as she tipped over the edge and began thrusting her hips up to meet mine. Her head bucked from side to side and I felt her cunt spasm in pleasure around my cock. This tipped me over the edge and I allowed myself to climax, the seed which had been roiling in my balls exploded out of my cock spurting deep into Sarah's pussy.
We lay there for a few minutes recovering ourselves then suddenly Sarah remembered the dinner.
"Oh shit, the dinner will be ruined," she said. "I had better got and check and check on it."
We both rushed into the kitchen. Fortunately Sarah had left the ring on fairly low and although the stew was bubbling away merrily it hadn't burnt. Sarah took a spoon and tasted it.
"Not bad, a little salt and I think that's just about ready," she declared.
She ladled out two bowls of the stew and cut us each a chunk of bread. I opened a bottle of wine and we both tucked into our meal with gusto.
When we had finished the food and were still sipping our wine.
"Do you remember how we met at that bizarre orgy at Lord and Lady Melksham's?" Sarah asked.
"Oh what a night that was," I replied. "Do you still see Caroline, she was quite a character?"
"I don't actually know her that well but I have seen her a couple of times since then, you know through mutual friends."
There was a pause in the conversation and I sensed that there was something else Sarah wanted to say but she was holding back from. At last she spoke.
"You remember what happened in the private rooms at that party."
"Of course it was amazing, I really enjoyed our experience together," I replied.
"Yeah, I enjoyed it too, but I think you wanted something more didn't you?" she went on.
"How do you mean?" I asked.
"Oh come on David don't pretend, you wanted by arse," she said no longer beating around the bush.
"Well yes of course I did, you have a bloody amazing arse," I said uncertain how to respond.
"But I knocked you back. I could sense you pushing in that direction but I was too nervous and bottled it," Sarah continued.
"It doesn't matter, we had an amazing fuck and I managed to lose my anal virginity with Lady Melksham," I responded.
"I know but ever since I have wished that I had had the bottle to try anal," Sarah explained.
"Well it was probably just as well you didn't try it with me because back then I didn't have a clue and would probably have put you off for good. Look at what happened with Safia," I said.
"I know but things are different now. I mean you know what to do and everything, don't you?" Sarah said hesitantly.
"Well I wouldn't describe myself as an anal expert but I definitely feel I have more of an idea now," I replied, beginning to realise where this might be going.
"So do you think you would be up for it then?" Sarah asked.
"Are you bloody serious? I would love to fuck your arse Sarah but only If you are sure it's what you want," I responded.
"You would be gentle wouldn't you David," she said hesitantly.
"Of course and one thing I have learned is to take it slow and use loads of lube," I explained.
"Oh that's OK I have some KY jelly, do you think that would do the trick?"
"That would be perfect."
Soon we had fortified ourselves with some more wine and made our way back to Sarah's bedroom. I was determined not to mess up this experience for Sarah and reminded myself to take my time. For a long time we lay curled together on the bed caressing one another and kissing. Eventually my fingers found Sarah's pussy again and began fondling first her lips, then her clit and finally pushing deeper and deeper into her moist channel. He vagina was becoming wetter and wetter in anticipation and every time I thrust into her dripping sheath of circled her throbbing clit she moaned in pleasure Her fingers found my hardening knob and began to caress it, grazing across my balls and tantalisingly circling my arsehole.
Then Sarah changed position and crouched over me, first nibbling the tip of my cock, then circling the head with her tongue and finally gently suckling on it with her lips. The sensation was indescribable. I wriggled myself so my head was positioned between her thighs and pulled her hip down so I could taste the delicious juices seeping from her cunt. I licked her dripping cleft from end to end, thrusting my tongue from time to time deep into her pussy and circling her swollen clitoris with my tongue. She sucked on my cock a little harder.
I thought I would experiment and see how she reacted to being anally penetrated. I moistened my index finger with her vaginal secretions and used it to gently circle her pink puckered opening. She paused and gasped slightly as my finger pressed more firmly against the tight aperture and then pushed past her sphincter just entering the tight ring of her anus. She didn't tense up or object so I pushed my finger in a little deeper and she gasped in pleasure.
"O God David, your finger is up my arse, that feel so naughty!" she exclaimed.
"It's not hurting is it," I checked.
"God no it's delicious!" she exclaimed.
I pushed my finger back into her pussy to coat it with more juices and then gently pressed it back into her arsehole. She wriggled in delight as I invaded her virgin anus once more with my slippery digit. Then I began to tongue her clit again as I finger fucked her backdoor. She seemed to have completely forgotten about sucking my cock and writhed on top of me uttering little cries of pleasure.
After a few minutes of this, Sarah moaned, "Oh David if you keep doing that I think I am going to come and I do so want you inside me."
"Oh OK," I said. "How do you want to do it?"
"I think I want you to fuck my arse now," Sarah announced. "The KY jelly is in the bedside cabinet.
She reached over and opened the drawer taking out a tube of the lube and handing it to me. She placed herself on all fours with her bum in the air waiting for me to lube her up. I applied a generous dollop of gel to my fingertip and gently pressed it against her tight rosebud. The previous penetration seemed to have loosened her up and my finger slipped easily past her sphincter and into her rectum. I coated the interior well and then went back for more to be sure.
"Oh David, that feels lovely and slippery," cooed Sarah. "Are you going to fuck me now?"
"Well only if you are sure this is what you want," I said.
"Oh God yes," she responded. "I have been wanting to lose my anal virginity for ages but just needed the right person. I think I can trust you Dave. I know you will be gentle for my first time."
"I feel honoured," I said. "Just one suggestion and that's that you lie on your side rather than doggie style for your first time. It seems easier until you get used to it."
"Oh OK," said Jackie and immediately lay on her side facing away from me.
I lay along side her and for a moment admired the plump curvaceous globes of her buttocks. She really did have the most magnificent bum. I took the KY jelly one more time and smeared a generous quantity all over my cock. I wanted this first entry to be as painless as possible. With one hand I eased her butt cheeks apart exposing the tiny pink star nestled between them. I loved the fact that a few blondish pubes curled around her back door. I grasped my prick and carefully lined it up against her back door at the right angle.
"OK are you ready I am just going to push into you ever so gently. If you just push out with your bowels as I do, that it will open you up and it will go in more easily," I said.
I pressed gently against her tight sphincter and then suddenly felt the muscles give and pushed past so my cockhead was just inside her rectum.
"Oh goodness, I can feel it going in. It feel enormous," gasped Sarah.
"It's just the tip but we will take it slowly," I explained.
I waited a few seconds and then began to ease my prick back and forth as gently as possible in her anus. Pushing forward millimetre my millimetre. At first I had to hold the base of my cock as it risked slipping out from her slippery little hole but as I got more of the head lodged fully in her back passage I was able to gently thrust to and fro leaving my hand free to caress Sarah's delicious body.
"Oh you are going deeper, it feels like my little bottom is getting really stretched," Sarah commented.
"Are you OK, I am not hurting you am I?" I asked.
"Oh not at all but it feels kind of weird like my bottom is really full but it's making me really horny, like this is the dirtiest thing I have ever done," she continued.
"Are you OK If I go in a bit deeper?" I asked.
"Oh yes let's go all the way," demanded Sarah.
I kept pressing inward still taking it slow. I remembered how badly it had gone when I had finally sodomised Safia and I didn't want this to end like that. Eventually after some minutes of gentle penetration I had my knob pressed deep into Sarah's colon. Her tight sphincter gripped the base of my cock tightly and I could feel the delicious plump globes of her bum pressing against my groin as I spooned against her. My hand wandered across on her well rounded breasts and I caressed her erect nipple. Then it slipped lower between her thighs and I found her moistened clitoris and gently circled it with my finger.
"Oh Jesus, that feel delicious David," groaned Sarah. "Don't stop but can you fuck me at the same time?"
I began to slowly thrust back and forth in her arsehole while I continued to manipulate her clit. I was rewarded with further moans of pleasure as Sarah enjoyed her first arse fucking. After a few minutes of gently buggering her as we spooned, I suggested we could now try it doggie style. Sarah was more than keen and quickly pushed herself onto her hands and knees. I knelt behind her and quickly applied some more lube to both her back passage and my prick before gently sliding it back inside her.
"Oh fuck, that feels even better," gasped Sarah as I slid my rampant cock all the way into her.
I began to fuck her a little quicker and reached forward to find her throbbing clit again. She began to moan softly as I reamed her arse while diddling her clit at the same time. I could feel her sphincter gradually relaxing and opening up as my cock slid in and out. Gradually the speed of my thrusts increased and I had consciously to control myself to stop coming. Her arse felt so hot and I was completely turned on by the sight of my prick sinking between the two plump globes of her delicious backside.
"Oh Jesus, I am so close to coming. Maybe if we change position and I finish myself off," she suggested.
She gently manoeuvred me to lie down on my back and then to my surprise straddled me cowgirl style. It was a little awkward but she managed to guide my throbbing cock back into her reddened hole and then sank down upon it impaling herself so the tip sank deep into her bowels.
"Oh man that's in deep, I feel so stuffed," groaned Sarah. "OK let's do this."
"She began to rise and fall on my groin at first slowly and then gradually faster, pumping my prick in and out of her anus. At the same time she began to pleasure her own pussy until she was feverishly rubbing it to and fro brushing her clit and outer lips as she built up to a frenzy. I had no option but to lay back and enjoy the delightful vision of her plump breasts swaying tantalisingly in front of me as her mouth opened and emitted ever louder sighs of ecstasy.
"Oh David, I think I'm going to come," moaned Sarah. "Are you going to come too? Are you going to squirt up my arse? Oh David I want your come in my arse."
Then she was coming violently and uncontrollably bucking her hips on me pushing my cock deep into her rectum. She had left off strumming her clit and now just pumped herself up and down on me waiting for me to come with her. I was more than ready and within seconds I could feel the rush o pleasure prefiguring my ejaculation.
"Oh Sarah, I am going to come too," I gasped. "Oh Sarah let me come up your sweet arse."
"Yes baby, fill me with your sweet come, do it now," she urged.
Then I was coming, it felt like in buckets. Every time her hips descended, engulfing my cock in her bowels, another shaft of pleasure ran through me and I squirted another rope of spunk into her rectum. At last we were both satiated. For a few moments she lay impaled on my softening prick. Then she leaned forward and we joined in long slow kiss until my organ popped out of her sloppy arsehole and we both giggled.
Chapter 15: Epilogue
The next day I said goodbye to Sarah and took the train back to university. Before I left Sarah drew me back to her bed one last time. She was too sore to let me bugger her again but we enjoyed a beautiful 69 session and then I fucked her pussy long and slow until we both came. Part of me didn't want to leave, the sex with Sarah had been wonderful but I wasn't sure that she was the one for me and I needed time to think.
A week or so later I was sitting on the coffee bar on campus and who should walk in but Safia. It was a long time since I had seen her and whenever our paths had crossed we had avoided talking to one another. To my surprise she came straight up to my table and asked if she could sit down. I motioned her to the seat opposite.
"Hi Dave, how are you doing," she asked.
"Oh pretty well," I said. "And you?"
"To tell you the truth I miss you," she replied.
"That's kind of surprising," I said, "I mean whenever I see you around you seem to want to avoid me."
"I know, I'm sorry," she went on. "I just feel sort of embarrassed how things turned out. I shouldn't have pushed you away like that."
"I guess I am to blame to for how things turned out," I said.
There was a pause and she took a few sips from her coffee.
"Listen is there any chance that we could you know have another go at things,"
I was knocked for six. A few months ago if she had asked to take me back I was would have crawled to her on bended knees but so much had happened since. I really did not know how to respond.
"Sorry Saf, I really didn't expect that," I replied. "Part of me really wants to say yes but I honestly don't think it would work. Too much water under the bridge and all that."
We sat in the coffee bar for another ten minutes. She didn't really seem surprised at my response and didn't really try to change my mind but it felt like we had a chance to deal with some unfinished business. In the end I had to go as I had a seminar in a few minutes.
"I hope we can stay friends Saf. You know say hello and maybe go for a coffee like this. I really loved you but I don't think it would work trying again. As I got up to leave she smiled and kissed her hand then waved it towards me. I almost turned back but forced myself to walk across campus without looking back.
- Regarding Jackie's offer, I pondered if I should accept her suggestion of learning anal sex properly, considering my past mistakes with Safia.
- In light of their shared interest in art, David and Sarah continued their conversation during their lunch break at the National Gallery, discussing Turner's masterpieces and his techniques.
