Living Two Lives - Book 4 - Cover

Living Two Lives - Book 4

Copyright© 2022 by Gruinard

Chapter 66

Coming of Age Sex Story: Chapter 66 - The adventures of Andrew McLeod continue. School is easy but the rest of his life is a complicated mess.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   Rags To Riches   School   Indian Female   Analingus   Oral Sex   Safe Sex  

Andrew had received the proposed marketing material from the Open University and had taken it to discuss with Mhairi. At first, she had questioned him as to why one of his parents wasn’t there. The truth was Andrew had been unsettled by his parent’s reaction to paying off the mortgage and was trying to keep them out of as much of his life as possible. He felt terrible even thinking some of his thoughts but had decided that the less his parents knew about the details of his life the better, especially the financial. Mhairi accepted the white lie that his father would sign any agreement with them but didn’t need to be involved yet. She had responded back to them and it had been agreed that he would be identified only as Andrew from Edinburgh studying Computer Science. Nothing was said about his age or still attending school. The photographs of him were all over the shoulder shots of him at a computer. Mary Young had taken a few shots on the last day of the residential course and there were several with lots of other students and a couple of him on his own but side profile only. There was no head shot clearly identifying him. The blurb was all factually accurate and just a retelling of the story he told at the Star Chamber session. Mhairi had given Andrew the okay to sign off the agreement which was surprisingly thick. Andrew thought this would have been two pages at most but it ran to closer to 10. He took it home and asked his father to sign it. Scott was crying at that moment and his father had not even looked at it, or even asked about it. Andrew made a mental note to give Scott an extra Rusk in the morning. By way of compensation or in lieu of a fee, the next two courses were free, courses six and seven of his degree were complementary. Two hundred and fifty pounds for saying true and nice things about the Open University. Andrew gave it no further thought.

Probably the best thing that came out of the evening photo session with Monica was that Andrew and Maggie’s friendship deepened. It was odd thinking of them as two separate people but it made sense in keeping the two of them apart. When Andrew and Maggie had first started meeting for a coffee there was not much difference between Maggie and her model persona. Now five months later she was herself with Andrew, still teasing but not being so blatant with it. And it was Maggie that asked the questions that arose after the first shoot.

“So do you want to do another shoot, to shoot me naked?”

“Wow, straight to the point.”

“When we talked after the shoot you seemed less, oh I don’t know, giddy maybe, at the prospect.”

Andrew thought about this and knew the way to answer it honestly was going to have him to reveal some things about his life.

“Okay, so the answer is confusing for me. I find myself drawn to the female form, a pretty face, big tits, nice legs, it could be anything. Now as a 12 or 13 year old I stared, and got caught staring a lot. You told me off the first time we met. From what I can understand talking to my friends and listening to the guys at school, it is a common thing. So there is part of it. But from lots of conversations and especially from making friends with girls at school, I have realised that it is.”

Andrew paused.

“I don’t know what the right word is. Wrong, tiresome, unwelcome, all these and more. So the person I am closest with at school is now a young woman who like you developed early. She turned up on the first day of there being girls at Heriot’s and she had the biggest bust in a year full of 14 year old boys. You can imagine the chat, what she had to put up with. So every time I catch myself looking at a woman but looking at just her physique or face, thinking of her as nothing more than a nice pair of legs or whatever, I then have to deal with this dilemma in my head, knowing that it is unwelcome or inappropriate but I am still drawn to the figure or face.

“It is that issue that gets me confused with you. I will be in the newsagents and there is a whole top shelf of men’s magazines. Hell there must be more than a dozen of them. So men like to look at naked women. Now I like to look at naked women so I understand that but I like to know the woman that is naked in front of me. Look, without going into any details, one of the reasons that I am not so over the top about seeing you naked is that I am having regular sex.”

“Really!”

“Yes. So part of me wonders if that is dampening down the excitement of the upcoming shoot. I really don’t know. Half of me is excited, half of me thinks I shouldn’t be excited and half of me is just plain confused.”

Maggie laughed at his maths. She started to speak twice before gathering her thoughts.

“It is fascinating to hear you talk about this. It is almost a female perspective. I have been at shoots where I will hear guys taking the shots say ‘Christ, look at the tits on her’, with no effort to whisper it. I am nothing more to them than a pair of tits.”

It took Andrew 20 minutes to explain about Leslie, and her sex-ed for a teenage boy.

“So she told you word for word what I just said?”

Andrew nodded. It was a couple of weeks later when they returned to the subject.

“I think I asked you the last time or the time before, if you still wanted to do the shoot. I had assumed, wrongly as it turns out, that I would be the first naked female you had ever seen, the small shy private school kid. Now look at you. I think your parents must stretch you on the rack at night and you are anything but scrawny. And apparently a bit of shagger, although you keep that pretty quiet. Now I think you can’t be bothered, you’ve seen it all before.”

Andrew didn’t think Maggie could pull her shoulders any further back.

“Stop that.”

Laughter and a relaxing of her posture.

“I have an odd perspective on this. It came to me one morning while I was swimming. When I am with a woman I like to please her. It turns me on to turn on a woman. I don’t know quite why that is, or even if it will change later, but right now it is probably my biggest turn on. In fact there is no probably about it, it is definitely my biggest turn-on. So when I think about the photo shoot with you I always come back to the comment you made to me months ago that you enjoy modelling, that it turns you on. And then there is the issue of how you have conditioned me into thinking about you modelling naked in a very matter of fact manner. The way we talk it feels like it is no big deal. You take your clothes off, men photograph you, they pay you and you get some secret enjoyment out of it. The presumption also being that the men get some enjoyment out of it. So all the bullshit breathless headlines in the papers are. Well bullshit. Does any of that ramble make sense?”

Maggie shook her head and smiled, an eerily familiar move.

“It makes perfect sense. I keep quiet about my modelling because of the breathless bullshit I would have to deal with, the tut-tutting from everyone, while at the same time more than half of those people would be checking out the photos. But you are right I am not ashamed of it and you and I have talked about it in a reasonable, sensible manner. When I stop and think about it, the main thing that is surprising is that it is with a 15 year old schoolboy. So turning it back to you, will you take part in the photoshoot, knowing that it will turn me on. And frankly it will turn me on knowing you are there.”

There was no attempt at making Andrew blush, he could see Maggie was being honest.

“Because I am so young?”

“I think there was some of that at first, like I said I thought this would be the first time for you to see a woman naked. Now. Who the hell knows. Part of it is your age, looking to corrupt someone so young. But part of it is you are my friend, although I don’t know why I want to be naked in front of you. But it is there. And the third is one I have been thinking about since you told me what turns you on. I think you and I would be a very good photographer and model, because there is a feedback loop. You know I get turned on modelling, you get turned on when a woman gets turned on, I know you are getting turned on which turns me on more, you see what I mean?”

Andrew didn’t have much blood flowing to his brain right at that moment but he did indeed see the point. And he enjoyed the little meetings with Maggie. It was normally only 40 minutes, and not every week, but for someone who was utterly different to Andrew she was easy to talk to. And about interesting topics. It struck him as strange to be having meaningful conversations with a junior typist at the City Council, often about intimate things. Yet at the same time he was not engaging in any kind of conversation with the daughter of a Court of Session judge who was planning to go to Oxford University. With her he just fucked her, for their mutual enjoyment.

Andrew’s tutoring with Moira was exam technique and keeping her calm as much as it was about the material. Moira was convinced she was going to fail the exam and it was a daily challenge to keep her calm. She came to the library every afternoon to study with him, and Suzanne sat away from them so he could focus on calming Moira. Andrew took to walking with her for 30 minutes after they had done studying just talking to her and positively reinforcing the fact that she could do it. She was needy and demanding during this time and she wanted sex every week. Andrew resisted at first as he was concerned that it was not doing any good. Moira might feel better about her body but it was not calming her mind. But this moment of conscious was ruthlessly squashed by his 15 year old self. Turning down regular frantic sex! Was he insane?

When Andrew went round to her house after school one day in early May he needed to think of something else. Once the housekeeper left Moira went upstairs and Andrew could hear a bath running. Apparently, they were going to do exactly what he had promised on that earlier visit. She shouted from the upstairs landing for him to hurry up and come to the main bathroom. The bath was rapidly filling with bubbly water and there was a jar of petroleum jelly on the side of the bath. He smiled at her obvious preparations. Moira urged him to get undressed and so Andrew got naked and put the condoms on the floor where he could easily reach them. He turned off the taps before Archimedes was proved right again and pulled a naked and horny Moira to him.

“Are you going to pass your Maths exam Moira?”

He asked her this between kisses. She wanted to jump into the water and was wriggling in his arms.

“Yes Andrew, come on, get in the bath with me.”

“No not yet. Every day when we meet you tell me that you are going to fail. You work yourself up into such a tizzy about it. So don’t tell me yes just so you can get your arse played with.”

He went and sat on the edge of the bath and then pulled Moira towards him, back first. He quietly undid the lid of the jelly and left it close to hand. Then Andrew ran his hands from her thighs up over the outsides of her hips, pausing them right in the position he would be holding her when they were fucking. He dropped down to his knees on the floor, right behind her. With his hands still on her hips Andrew started kissing and nibbling each of her cheeks.

“You have such a wonderful arse. So plump”

He kissed a cheek.

“And round.”

He kissed the other cheek.

“And padded.”

Andrew ran his tongue through the top of her crack right at the small of her back.

“Six months ago you hated your arse and now you cannot wait for me to run my tongue all the way up your crack. I can smell your arousal as you wait for me to lick your tiny little rosebud. Grease up my finger and invade you. You want me to pick you up and lift you into the bath.”

As he said that he stood up and lifted Moira into his arms. Carefully he climbed into the bath and put Moira down. He went back down onto his knees.

“You want me to start washing your arse, running my hands all over it.”

Every action he described was copied with his hands.

“Run my fingers from your dripping pussy up to your tight little arsehole. You want me to tell you to bend over and grab the taps, while I spread your cheeks and start fucking your arsehole with my tongue.”

Moira was bent at the waist thrusting her bum back at him. Her bum was spotless. She had cleaned up in advance of his arrival and Andrew dove in with no reservation. The resistance to his tongue was amazing. This was a tight virgin sphincter. He licked away and then made stabbing motions with his tongue. It always bent against the resistance of the muscle. Andrew let go one cheek and coated both middle and index fingers of his right hand in jelly. He could feel Moira tense in front of him as he made sure they were well greased up. Andrew slowly circled his fingers round her rosebud, spinning his fingers both clockwise and counter clockwise. Then without warning he firmly pushed his middle finger through the ring into her arse.

“Aaah, oh right there. Deeper. Oooh.”

Andrew sawed his finger in and out of Moira’s arse and she thrust her hips back and wriggled her arse trying to embed the finger even deeper. He pulled the finger out and repeated the circular motion before stabbing through the ring again. Now Andrew had not touched her pussy yet that day. Nothing. Her reactions were all from the sensations in her bum. Andrew continued to pull out, caress her sphincter and then reinsert his finger. This went on for several cycles but then rather than insert only his middle finger he pushed down on her arsehole and both fingers popped in. Moira squealed and was still. He didn’t know if she came or not but she was rabidly turned on. At the same time he could sense that she was dealing with the physical invasion of her body.

Andrew leaned over and grabbed a condom and awkwardly opened the packet and got his dick wrapped with only his left hand. He stood up and thrust hard into Moira. Water was flooding everywhere it was a complete mess. But he grabbed her hips and held on as she thrust herself against him. She was fucking him more than the other way round. The jelly was still to hand so Andrew jammed his thumb into it and then started playing with her arsehole, all the while screwing her as hard as possible. It was all too much for both of them and they came hard. Andrew pulled the condom off and dropped it on the floor beside the bath, he would worry about it later. He pulled Moira back so that they were sitting in the standard nesting position, her back resting on his chest with his arms around her.

“Every week, and every week until the exam, you will get that and more. But only if you start to think positively about the exam. You come in every day all freaked out then I won’t do that for you. You will wake up, knowing that you can pass the Maths exam, the last maths exam you will ever take. You come to school and review the material with me and exhibit a positive attitude then I will do that to you every week until the exam.

“And Moira, if you do that. If you show everyone the confident you, the positive you, the you that knows all the material and could pass the exam tomorrow, if you do that, then on the night before the exam I will take you to bed, lube up your tiny little rosebud and I will fuck you in the arse. That will be your incentive. Get to the exam proud and confident knowing you will pass and this will happen to you Moira.

“You will wake up that morning knowing you are going to get fucked in the arse that afternoon. And fucked just the way you like it. Head down, hands braced against the headboard, arse up, and your tiny, tight, delicate little arsehole glistening with the lube. I will have kissed it and licked it and fingered it for hours. All that will be left is for me to push through that tiny little muscle. Have you thought about it?”

Andrew was caressing her breasts now and tweaking her nipples

“You have, haven’t you? Do you think you are going to come when I enter you?”

Andrew stopped talking and kissed her neck, all the while rolling her nipples in his hands. Slowly he stopped and just held her in his arms. After a while the water started to cool and so they got out the bath and spent the next 20 minutes drying the floor, cleaning up and trying to get it back to reasonable order. They walked back into her room carrying their clothes and got dressed.

“I really can pass this exam.”

It was a statement not a question.

“Yes you can. We would be spending time on the material if I was worried. We spend more time just fighting your demons than anything else.”

“Thank you, Andrew. I don’t say that enough. Not only do you know the material and have taught me well but you understand me. The word pictures that you paint. Oh my god Andrew. I will work on my attitude and outlook and will hold you to your promise.”

It was an unusually tender moment between them. In the end Moira calmed down a lot and her freak outs were much fewer. Andrew kept her stress level down each week as he promised until the night before the exam. He would have loved to have memories of the glorious culmination of months of build-up and the long, frantic, mutually satisfying occasion that happened. Sadly it was nothing like that. When he went to actually do the deed it was tight, painful, awkward and more. Moira’s scream at the moment of penetration was an instant dick softener. The whole thing was a complete failure, probably because of their inexperience and lack of preparation, and they stopped immediately. They both felt terrible about it and were more worried about the other than themselves. The last time that Moira and Andrew ever had sex was the closest to making love that they managed. It was a long slow screw face to face with kisses and whispered thank you’s. Even the next day he didn’t remember whether either of them came. It was the coda to their arrangement, they both knew they were done. Moira was ready to take the exam and Andrew was done tutoring. It had been an exhausting year. Once they were dressed he held her in his arms for the last time.

“Let me know when you pass and good luck at Oxford. You are going to be a hell of a lawyer and make your dad very proud.”

“Thank you for everything. Of course I will tell you how I do in the exam.”

She pulled him tight in a hug. But there were no entreaties to visit, there was no false hope of keeping in touch. Life was moving on.

The freed up time let him move ahead with the work on module three of his 5th computer course. His regular school studies were going well and the two Ordinary grade exams in Arithmetic and Latin were straightforward. Tanvi and Katie were also off on exam leave and studying for their Highers. They were both capable students and they never talked about school work when they were out with Andrew. They used the Saturday nights as their release from studying. For a couple of weeks they went out together, the three of them, just so they had some time away from the books. Tanvi would go over to Katie’s and they would leave from there. Andrew would escort them back and then head home himself. At first they were hilariously awkward when it came to kissing in front of the third person. They all got the giggles about it. Tanvi’s solution was that the third wheel would close their eyes and count slowly to twenty. Then they would switch. Yes, Andrew knew he was the luckiest bastard in the whole world. By mutual, but unspoken agreement, everything was on hold until after the exams. This whole situation had enough complications as it was without adding exam stress to it. Who knew what the hell was going to happen over the summer?

Andrew’s summer plans for the first time in three years were flexible and even had potential free time. There were eight and a half weeks of vacation, the school went back on a Thursday at the end of August. He had the CCF camp the first week and two weeks for Harry in August, with a three day hockey clinic on one of the weekends right before he was at the farm. The middle five weeks were free at that moment. His mum and dad were going with Rowan and Scott to Sweden but it was scheduled at the same time as when he was working at the farm, so he wouldn’t be at the house on his own. His parents trusted him but not that much!

The term was more than half complete and other than talking Moira down off the ledge a couple of times it had been drama free. The hockey training on Thursdays was okay. Hendricks had selected a couple of 6th years who were in the first eleven to work with him. They were friends with each other and used the time as a break from studying. They were nice but not overly friendly. Their job was to make him better, as they put it ‘passable’; they weren’t mean but they didn’t cut him much slack either. They treated it as a job and important and there was a cold professionalism to them. He was a teenage boy two years younger than him, almost beneath their notice. It worked though as Andrew was getting better and he could hit consistently more and more, including all three aspects of the penalty corner. He had signed up for the coaching course so was committed to getting as good as possible in his weekly training sessions.

In the middle of May, he had finished tutoring Moira and had sat his own two exams. For the 4th years it was a time when the teachers kept the pressure up. They were the most advanced pupils with classes as the two most senior years were all off on study leave. The homework seemed to intensify and they were busier than any of them expected or anticipated. Andrew got home late one night from a study session at school followed by some more reading at the City Library. His mum was waiting to talk to him as soon as he walked through the door.

“Andrew, the Open University has called three times. They want to talk to you. Sue Conway is staying late waiting to talk to you. What is wrong?”

As usual with his mother’s rapid-fire questions when he got home Andrew had no idea, he had just got there. But underpinning it was her concern that he had done something wrong and ‘what would the neighbours think’. His mother was nothing if not consistent.

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