Living Two Lives - Book 11 - Cover

Living Two Lives - Book 11

Copyright© 2023 by Gruinard

Chapter 6

Coming of Age Sex Story: Chapter 6 - The continuing adventures of Andrew McLeod. This book covers the third term of his first year at university.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Rags To Riches   Light Bond   Anal Sex   Analingus   Exhibitionism   Oral Sex   Safe Sex  

Helena lay across Andrew, delightfully dishevelled, with a smile on her face. Her ability to bounce back from spectacular orgasms within 30 seconds was amazing. He was still trying to recover his breath and his focus on the world while she had this expression of ‘what have you done for me lately’.

Helena’s parents were not back in the Great Court after leaving before she was in Andrew’s room. The look in her eye when he opened the door was full of promise. Helena Innes was a smart lover, she knew how to engage Andrew’s mind and was cunning in how she did it. He locked the door behind her before sweeping her off her feet and giving her a big hug. Helena flung her legs round him so he managed to get his hands under her arse to support her and they kissed for long seconds. She broke the kiss and leaned back to look at him.

“I am so fed up with pathetic boys, acting like I should be grateful to spend time with them, that I should swoon with fervour at their insipid wooing. God, I need a man. A man who knows how to treat a woman correctly.”

She unhooked her legs and Andrew lowered her until she was once again standing. But Helena continued to slide down until she was on her knees in front of him.

“Strip.”

It was a command and after some undignified hopping around Andrew was naked in front of her. Her hand was small and cool and his dick twitched as she grasped it firmly. She began a gentle motion but all the while looking him in the eye. Nobody did this better than Helena, she had the most wonderfully expressive face and could convey a look of carnal innocence that was ball draining. The phrase is almost an oxymoron but that was where the mental part of their fucking came in. They had talked about this post-coital many times and Helena knew how to push his buttons. The whole look of ‘I can’t believe you have talked me into this again’ mixed with ‘you won’t last 10 seconds’ mixed with a look of naiveté or innocence. Was any of that there? Some maybe but most of it was in Andrew’s mind. And Helena was a clever woman. Now this time rather than convey all that with her eyes aided by her lips and tongue she was able to talk to him, all the time gently jacking him off.

“Is this what you hoped for when you gave me the scarf? A thank you blow job? When you were standing in the store looking at the display was this what was going through your mind?”

She let go, put her hands on his arse cheeks and tried to get as much of his dick in her mouth as possible, just for a second, before pulling it back out.

“What are my eyes showing Andrew? Can you tell how much I loved the scarf? Are you going to make me wear it while you fuck me? Would you like that Andrew? Naked but for the scarf. Maybe I should stop right now and go and get it. I think if I did that I could turn your balls inside out. Do you want me to drain you Andrew? Do you need to come?”

Helena knew she had him at the point of no return and simply popped the head of his cock into her mouth. She choked a little on the first blast as it sure felt like it shot out at a hell of a speed. But nothing was spilled and she looked at Andrew with smug pride as she swallowed the lot. He held her shoulder for a second to steady himself before helping her up and kissing her soundly. Andrew just held her for a few moments letting his heart rate return to something close to normal. He spun Helena round and leaned in to start nibbling and kissing her neck. She melted into his arms and he stripped her; not frantically, not slowly, but determinedly. But rather than just throw her onto her back and dive between her legs Andrew got Helena to lie face down on the bed. Using a little baby oil he had bought for this purpose he oiled and massaged her body, from neck to ankles. Andrew paid a lot of attention to her bum, ensuring that the oil was thoroughly absorbed across both cheeks, but spent as much time on Helena’s shoulders, thighs and calves. It was sensual and relaxing with the focus on building up the sexual tension between them. It worked very well as by the time he finished with her right foot and ankle Helena’s legs were spread and her back was arched pushing her arse in the air and allowing easier access to her pussy. Taking it a step further he grabbed a pillow and raised her bum even further as he slid it under her.

When he started to massage her arsehole and pussy there was no flinching, no expression of doubt. Helena seemed to be purring from the attention Andrew was paying to her. The teasing had worked, she was revved up and so now he adopted a more direct approach. Slipping an oily finger into her pussy he gently pressed down on the roof, putting pressure on her g-spot without scratching the itch as it were. Helena immediately started to move her hips in search of greater stimulation.

“Patience.”

He gave her cheek a gentle swat before turning his attention to her pretty pink rosebud. Again there was no dissembling, it was already glistening from all the oil over the last 30 minutes and as Andrew stabbed at it with his tongue he could feel it flex and bend. He heard a hissed ‘yes’ from Helena and renewed his attentions with vigour. This was a young virgin arsehole, untouched other than an occasional finger from him the previous term. His tongue was going to bounce off that from then until eternity. So Andrew reintroduced Helena to his index finger, pushing it through the tight muscle. He was now caressing her g-spot with two fingers of his right hand while gently sawing in and out with the index finger of his left hand. A slightly more intimate version of walking and chewing gum at the same time.

Previous encounters had shown Andrew that he was not ambidextrous, so he just pushed his index finger into Helena’s arse and then concentrated on her first orgasm with his dominant hand. Once he focused on doing one thing well Helena built to the boil quickly and bucked her hips under him so severely he had to remove his finger from her bum to avoid injury. Knowing Helena’s quick recovery he gave her little respite but now focused on her arse. Re-oiling his fingers he started a more determined investigation of her beautiful bottom. One finger was slipping in and out with no issue but when Andrew tried to squeeze in a second finger she grabbed his wrist and he heard ‘slowly’ uttered in a breathy voice.

The sphincter is a muscle and as such can be stretched, but it required patience and tenderness. For successful anal sex you had to stretch the sphincter to accept a dick. Andrew’s issue was not the slender shaft of his cock, that was not the problem. His issue was the wide ‘mushroom head’. Insufficient preparation and lack of experience had doomed his first attempt with Moira all those years ago. So he was patient with Helena, too patient judging by the sounds emanating from her. But eventually two fingers were sawing in and out easily and he got ready. Wrapping himself up Andrew oiled up the outside of the condom thoroughly and reapplied copious amounts to Helena’s slightly gaping arse concentrating on getting plenty of oil round and in her arsehole. Then he knee walked between her legs and lined up the oily head of the condom. In those early years Andrew had so little experience that it was still trial and error, more error to be honest. For the longest time he would be slow and patient without realising that this was increasing the time that the sphincter was stretched the widest. Although it was counter-intuitive at the time the easiest way to deal with the initial penetration was quick and determined. It allowed the sphincter to spring back around the much slimmer shaft of his cock and for the pain to pass in a moment. But it took a while to realise all that.

That afternoon Helena oophed and grunted but suddenly Andrew was in. He stopped to let her get her bearings, as well as to determine if this was something she wanted to continue or stop immediately. The phrase they had used was sexy taboo and that was where her mind was. After a few seconds to let the pain subside Helena looked over her shoulder at him and nodded. Using tiny movements at the start Andrew gradually got deeper into her and his thrusts became longer. Helena still had her face towards him and slowly the look of intense concentration gave way to a more relaxed one and right before his eyes he could see her start to get into it. There are nerve endings around the sphincter, they are concentrated there the same way the nerve endings in the vagina are concentrated at the entrance. It is the movement and stimulation of them that creates sexual pleasure. The g-spot had achieved such mythic status partly because it was one of the only areas within a vagina that increased pleasure. So Andrew didn’t expect Helena to orgasm from anal sex, at least not directly. Two things would assist in her achieving the same pleasure as he was. Clitoral stimulation by one or other of them was the first and the second was her own over-active imagination. Andrew leaned down and managed to contort his neck to give her a kiss. Then it was time to talk.

“Do you want to know what I was thinking as I stood admiring the scarves, thinking about you, how you would thank me? I was thinking about this right now. All slick and oiled up, pussy leaking from your sexual desire. But I was thinking of you just like this, your beautiful tight bottom split apart as I buggered you.”

The first shudder.

“I saw it in your eyes at Waterloo station on the Thursday morning. You gave me a hug and a long kiss but it was but a mere down payment. I looked in your eyes and there it was. That brilliant inquisitive mind, wanting to try and experience new things. No more playing around, no more delicate fingers, gentle exploration. You wanted to be buggered. You wanted to know what the big deal was. Is it everything you imagined? What does it feel like Helena? Invasive? Uncomfortable? Because let me tell you it feels fantastic to me. Hot, tight, grasping. Yes all of that. But it is the visual Helena. Your cute little arse, glistening and gleaming.”

Another shudder.

“You know that I can’t look down, I will come immediately. The visual of my cock splitting your arse, sawing in and out, oh my that will be too much.”

As usual Andrew talked himself into an orgasm as much as his partner. Helena felt him speed up and reached under her to play with her clit. Andrew could feel his own orgasm on its way and so looked down and it was game over. He really was an arse man. He tried to drive Helena through the bed as he came and when he was done, lay on her, not letting all his weight crush her. Just as he started to shrivel Helena’s ministrations finally worked and she too came. All too soon the need to clean up and dispose of condoms got him out of bed. He soaked a washcloth and knelt beside the bed and carefully cleaned up Helena’s bum. Her sphincter had sprung back but it looked red and sore. Even with gentle dabs he heard and saw her flinch. When he climbed back into bed Helena was on top of him immediately.

“So a simple thank you wasn’t enough?”

Andrew had cleaned his teeth, and brushed his tongue, so kissed her for a long time. When they separated they dozed, Helena lying across the top of him, for 10 minutes or so.

“How are you feeling?” he ventured.

“Weird, a bit achy back there but other than that I am fine. You took your time and really other than getting that fat head of yours in the rest was pretty simple. I loved how you flung my words back at me. That is the thing that you get that no one else I have been with does. Sex with you is not just the physical act it is this mental game. And most importantly the game is about the other person. I love how you react to the way I look at you when I am giving you a blow job. I feel so in control when I can hold you off or make you come depending on my look. Sure there is the physiological feeling but with you it is the story behind the act that makes it so much better. I think you are also honest, I love how you talk yourself into orgasm as much as me. The way you describe my body, what we are doing, what you see, it is very.”

Helena paused.

“I don’t know exactly. Take my arse as an example.”

That made them both laugh.

“Okay, now that you have taken my arse but the point is I never understood it before. The way you describe it, the way you almost worship it, that was a complete eye-opener to me. It still is. All women know that men are visual creatures but it is as if you have lifted the veil even further. The dynamics of gender confuse and fascinate me all at the same time. I don’t want to be defined by my arse, I am a strong clever woman trying to make my way in a world still dominated by men. At the same time I love how you are honest about my physical attributes. That is where you are different Andrew. You treat me no differently than Navya when we are outside our rooms yet you make me feel desired and feminine when we are together. I was right about one thing at the beginning, you are a man not some pimply boy. I am so sick of the attentions of grabby boys. They might be 24 but they are still grabby boys.”

Neither of them was exclusive and they both knew it so Helena gave Andrew the five minute version of her month at home in Hampshire. It was the frustration of these unfulfilling encounters as much as anything else that had made her question the changes that university was bringing. What was the phrase from school? Every guy needs a Leslie. Five years later and it was as true as ever.

“You never talk about other women Andrew, even when I talk about what I have been up to.”

Again it was part statement and part question.

“I never have. Well with one exception. And actually because I am a complete slut there is a chance that some of my partners could meet. I don’t want them to be looking at each other thinking that about each other. Nobody knows about anyone else. I have found that it is the woman who talk, like I know that you have with Navya and Abigail. I told Pedro that he could walk into my room and find a naked woman on this bed and I would still insist that we are just friends. He is getting a bit better. Matt is much better, and the other two guys that I hang out with at OTC are getting there as well. Well actually Rollie is doing fine, whereas Jack just strikes out the whole time.”

Helena laughed but turned serious.

“Does it bother you that I have talked about us to Navya and Abigail, and through them Rupashi and probably Emma?”

Andrew pondered the question for a few moments.

“Yes and no. An annoyingly vague answer but I would prefer if no one knew but given that you appear to enjoy it so much all I can say is at least you are talking about me in a positive way. I know that is vain and shallow but I would be lying if I said it didn’t please me a little. The other thing is I know and talk to a bunch of women but other than a one night stand at the end of last term you are the only person I have had sex with here at Cambridge. All the other women here really are just friends.”

“I know what you mean, it feels disloyal somehow to be trying to take another man to my bed 20 feet down the corridor from you. And I know we are not a couple but it still feels odd.”

“I know exactly how you feel. It was like that with Emma at the start of the year. She was so determined but at the same time so cack-handed about how she did it. I mean the week before you and I had spent a relaxed day together and it all happened smoothly. With her it was all very, oh I don’t know, clinical somehow. Something to be ticked off on the list of things to do when you get to university. She is pleasant to me but she never hangs out.”

“You are forbidden fruit now Andrew. She tries not to torment herself with you, that is all.”

He decided to interrupt the ‘pat Andrew on the back’ session. Taking Helena’s hand Andrew directed it towards his groin while he leaned over and started gentle kisses and nibbles to her sweet nipples. Helena smiled but took the hint and within a few minutes he was revived and ready to go. After wrapping up Andrew pulled them up the bed so he was sitting back, leaning against the wall and Helena climbed into his lap before gingerly lowering herself onto him.

“Oh this is nice Andrew. Thank you.”

Andrew guessed that she was tender and so they slowly coupled. It allowed for caresses and kisses and was a nice counterpoint to their earlier efforts.

“Andrew, take my cheeks and gently, really gently, squeeze them together.”

He did as she commanded and as he pushed them together she ‘oophed’ almost theatrically.

“Oh that is good. Pushing the skin around is perfect. Touching would be too intense, too soon but that is nice, I can feel that, it reminds me of earlier but in a nice way. What did you call it? A sexy taboo? That is exactly right. You were considerate and patient but there was also this aura of inevitability to it. We both knew this was going to happen and you had decided it was going to be today. Now when I am squirming in the library tomorrow with my arsehole on fire then I might not be so forgiving.”

In response to that Andrew squeezed her cheeks again and Helena smiled before kissing him once more.

“Slide down, flip me on my back and make me scream with pleasure Andrew. Come on. I am not made of porcelain.”

12 minutes later Andrew was gathering his wits about him while the delicious Helena looked all freshly fucked and gorgeous on his chest.

“It is amazing how you can be wiped out screaming for mercy and then a minute later you look so bloody adorable lying here. I can barely remember my name and you look wilful and mischievous.”

He squeezed her cheeks gently and his only response was a breathy ‘yessss’. Hoisted by his own petard.

“I am joking. I may look like I am back under control but in reality, I am just as wiped out as you. I feel all stretched out down there, and ache in a nice way. There is Formal Hall tonight, do you fancy going over. It should be pretty quiet and maybe we can go for a walk after. I would like you to sleep over at mine tonight, I don’t think for anything other than sleeping the way I feel, but I like falling asleep in your arms.”

Dull David the rower in number 9 was the only other person in the corridor back that night and so the three of them joined the end of the farthest table beside an archeologist and a historian. The conversation was light as they normally were at Formal. Often, Andrew would be beside students or post grads with the strangest specialities and you had to find common ground. Some nights it was slow and painful but more often it was fun and enlightening. But there again he was a geek and enjoyed learning about new things. David wandered off with the rowing crowd, a sizeable faction at most Colleges, and Andrew and Helena changed out of their formal clothes and walked arm in arm through the Courts and out the back of the original part of the College.

“I have decided I am going to try and be more discreet about us this term Andrew. Freya told me I needed to grow up and she is right.”

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