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The curtains billowed in the gentle evening breeze from the Aegean Sea, but the room was quiet except for the hiss of the cicadas in the trees beyond the villa’s balcony.
At dinner, my companion had worn a short summer dress with a plunging cleavage, which had brought frankly lustful glances from many of the men in the restaurant.
Now our few clothes were scattered around the room, and she was astride me.
For the hundredth time that summer, I ran my hands over her heavy breasts and the fine crisp curls between her legs.
It didn’t matter that she was twenty years older than me; we had the same needs and drives. We could catch up on sleep during the siesta hours. The night was for sex.
She gripped my stiff cock in her hand and slowly lowered herself onto me, gasping as I entered her.
I was just a graduate student. How had this gorgeous, sexy woman come into my life?
* * * * *
I’d recently moved to a small but well-known university town in southern England, where the engineering department had accepted me onto a one-year postgraduate course. The university’s accommodation office found me a quiet one-bedroom flat, and I settled in to the program of lectures and written work.
The first thing my parents had mentioned when I told them my plans was that Gillian lived there. Gillian was the younger sister of one of my mother’s circle of friends, and my parents had known them both since school. Now in her early forties, Gillian was divorced with a twelve-year-old daughter called Bridget, and worked as a mobile mortgage broker for a local estate agency.
You needed a good maths background to keep up with the demands of the course, and I enjoyed tutoring. About two weeks after term began Gillian sent me an email saying she’d heard via her sister that I was living nearby. She asked if I wanted some extra paid tuition helping Bridget with her schoolwork, and gave her mobile phone number.
Which is why I was ringing her doorbell at ten one Saturday morning.
I hadn’t met Gillian for years and didn’t expect her to recognise me, for I had grown and filled out since school. Although I had little inclination for team sports, I’d developed considerable core strength from walking and climbing while doing my first degree, and kept as fit as possible for weekend excursions to the Welsh mountains.
As soon as she opened the door, I could see the resemblance to her older sister. She was a good-looking redhead with pale, freckled skin, tall but still a little shorter than me, with short curls and high cheekbones. A few wrinkles were set off by a dazzling, friendly smile, and a well-tailored business suit with a name badge didn’t hide the fact that she curved in all the right places.
I thought she was one of the most attractive women I’d ever met.
In a soft Irish accent Gillian welcomed me warmly and introduced me to her daughter. We quickly arranged that I’d come round twice a week for half an hour at a time to help Bridget with her maths and physics homework.
* * * * *
The arrangement worked well. Bridget was a bright and enthusiastic kid whose only problem had been bad teaching. Under my guidance her grades started to improve rapidly, which delighted her mother. Also, Gillian was good company and often invited me to stay for a drink after the lesson. Despite the difference in our ages and backgrounds, we quickly became close.
In the second month I started to help out about the house, setting up a network router and a new printer, and even babysat one evening when her usual sitter had to cancel. Well, it wasn’t much of an ask; I brought my textbooks and laptop and worked at the dining room table. She was very grateful when she came back from the client dinner, and told me how much she appreciated having someone she could trust to keep an eye on things. Of course I wasn’t going to take any payment, so she gave me a bottle of whisky instead, which I couldn’t refuse.
Gillian’s sister and my parents were pleased that I was helping out a family friend.
And there things might have stayed. Gillian was an attractive woman, but she was almost twice my age.
Until I got a text from her asking me round for lunch, and to ask a favour.
* * * * *
Over grilled fish and salad she told me some personal details. She’d been out of the dating game for several years after her marriage had ended and was seeing a therapist. Her ex had been abusive in various ways, so much so that she’d lost confidence in her own attractiveness. Only a considerable amount of courage allowed her to leave him and take her daughter.
Now her therapist was encouraging her to start dating again, and had suggested she find someone with whom she could take things slowly and work on some ‘intimacy exercises’ that would build up her confidence. Gillian didn’t really know anyone suitable in the town, and thought a mature singles site might link her up with someone.
Now she wanted to ask my help, both with setting up a computer dating site account casino siteleri – which was easy – and on how to write a profile. She’d had a good photo taken and had put some ideas down on paper.
She showed me what she’d written. To my surprise, it described a no-strings relationship.
“The photo does you justice. It’s great.”
“But I’m not sure about the text. You’re looking for someone who will put your needs first. If you post this, you’ll get plenty of replies. But I know what these sites are like. They’ll all be from the wrong sort of man.”
She looked downcast. “That sounds like good advice. Perhaps I should just drop it.”
And then I had an idea, because I genuinely wanted to help her. “Can I suggest something? This might not be appropriate. But if it’s just a question of finding someone to work with to build up your confidence, how about me?”
She said nothing for a moment, thinking about it. “In some ways that would be ideal. But I’m much older than you are. Would that be a problem?”
“Of course not. I’d just like to help you out. I certainly don’t want to see you hurt by some creep off the Internet.”
“That’s very sweet of you. But only if you’re quite sure you want to.” She gave me a dazzling smile. “Actually, I did think of you. Several times. But I thought you might be too busy.”
She wasn’t sure what the ‘intimacy exercises’ involved. The therapist, one Doctor Macrae, would direct her from week to week, depending on progress. The only guidelines she’d given were that Gillian had to be comfortable and relaxed with the partner. Most critically, they each had to respect each other’s boundaries.
Sensibly, her therapist had insisted we agree on a set of ground rules, and we added a few others. There would be two or three sessions a week. Either of us could bring the sessions to an end at any time, and we’d only meet when she had the house to herself.
We decided to be discreet about the arrangement, especially where our families were concerned. Gillian was almost twenty years older than I was, and what we were arranging was, at the very least, unconventional.
Which was fine with me. I was glad to be able to help her. But the boundaries would stay firmly in place.
Unless she asked me otherwise.
* * * * *
The therapist had asked us to start with massage, so that’s what we did.
In the master bedroom, I faced the curtain while Gillian quickly stripped off. When I turned back, she way lying face-down on the bed, wearing nothing but a pair of loose black panties. There were freshly laundered towels on the side table and a bottle of massage oil, and more towels on the bed to protect the duvet cover.
I sat beside her, oiled my hands, and ran them up and down her lightly freckled shoulders and legs, respecting her personal space by carefully avoiding her knickers, but going as far down as the curve of her lower back. Quickly I got into the rhythm, digging into the muscles of her neck and spine; massage is hard work if you do it properly.
“Not too firm?” I asked.
“That’s lovely, please keep going,” she murmured, but a minute later she asked me to stop for a moment. “Do you mind doing my bottom too?”
“Of course. But I might get massage oil on what you’re wearing.”
“Wait a moment.” Gillian raised her hips and quickly pulled the panties off, dropping them by the side of the bed. She was still face down, but naked.
I asked if I could kneel between her legs. Wordlessly, she spread them apart for me. Now I could run my hands all the way from her shoulder-blades to her firm bottom, and down to her thighs and calves.
In that position I couldn’t avoid glimpsing her pubic hair, which excited me but gave me an erection I didn’t need right then. I assumed the view was accidental on her part and certainly wasn’t going to embarrass her by mentioning it.
I worked at her muscles for twenty minutes or so. Eventually she asked me to stop. “That was wonderful, thank you! I haven’t had a man touch me like that for – oh, a long time. You have gentle hands.”
I looked away again while she put her panties and a tee-shirt back on. “Your turn now.” I stripped off to my boxer shorts and lay face-down on the bed. “Mind if I get on top? Best position to do your back.” She straddled me and began to rub massage oil into my shoulders.
In the mirror I could see her heavy breasts swinging under her tee-shirt as she worked on my shoulder muscles. I looked away and managed to bring my body under control before she finished. She was, I reminded myself, a friend of my parents, and therefore off limits.
She gave me a kiss as I left. “Thank you. That was wonderful. And I feel very relaxed.”
I felt pleased for Gillian that the session had gone well, but also very horny, and wondered if I should continue. As soon as I got back to my flat I stripped off and had a shower. Seeing Gillian’s pussy while I massaged her was a huge turn-on, and I turned the water temperature down as slot oyna cold as it would go.
* * * * *
“I talked to the therapist about you and how it went. She was very pleased and says you are exactly what I need. So, cheers!”
It was two days later. Gillian had opened a bottle of wine and we were back in her bedroom. She was wearing a black silk robe and I had my usual chinos and polo shirt on.
“So what’s next?”
Unexpectedly, she blushed and halted. “I had a long talk with Dr Macrae. She says we now have to start working on the ‘intimacy exercises’. The idea is that, well, I have to be comfortable naked in front of my partner.”
I nodded. “We just have spend time together undressed. Look, I understand if that’s too going far. After all I’m, the mother of one of your students, and a friend of your parents. So if you think it’s inappropriate, just say.”
“It’s no different to being on a nudist beach,” I said. “Besides, the whole thing is private between us and the therapist. So I’m fine if you are.”
“Of course. And I hoped you’d say that. Because we like you a lot. I’m so pleased about how you’ve helped Bridget. It’s lovely that you care about us. So, yes, I am comfortable with you.”
She met my eyes and smiled, then dropped them. She was still blushing, which made her look even prettier. My imagination was working overtime. But that just made it more important to behave appropriately with her.
As before, the bed was neatly made, and the lighting was turned down. Sitting on a low upholstered chair close to the bed, I crossed my legs.
“Shall we start?” she asked. I nodded. “The rules are that you can look, but you can’t touch. For both of us.”
Gillian stood in front of me. Slowly, she undid the waist tie, dropped the silk robe to the floor and stood naked in front of me.
For a woman in her forties she looked fantastic. Her breasts were large, pointed, and tipped with rosy nipples. She had strong, smooth legs; a few stretch marks from her pregnancy, which didn’t bother me at all; and a neatly trimmed bush that I’d glimpsed during her massage.
“You look fabulous,” I said, and wasn’t exaggerating. She smiled.
“That’s nice to hear. I’ve not had that sort of compliment for a long time.” She twirled round and put her hands on her hips. “I’m glad I asked you. I realised I couldn’t have done this with a stranger off the internet.”
“Just do what you feel comfortable with,” I said. “You have a fantastic body. I could look at it all day. Shall I get the massage oil again?”
“That would be lovely.” Again, she hesitated. “But…” She looked at me. “This is a bit naughty, but Dr Macrae said I should go for it if you’re OK. She said it would really help me.”
“I always had a fantasy about touching myself with somebody watching. Do you mind? I can stop any time you want.”
I didn’t mind at all. We were in complete privacy, and this was what her therapist had suggested.
I sat back in the chair and Gillian lay on the bed. She closed her eyes, moved a hand down to her bush and parted her legs slightly. Slowly, she began to run a a finger up and down the dense red curls of her pussy, gently stroking herself and glancing at me occasionally.
I realised she was putting on a show for me while she pleasured herself. This time I couldn’t hide my erection.
“Do you like watching me?” she asked. “Is it turning you on, watching me masturbate?”
“Yes.” My throat had gone dry, and I took a sip of water.
“Dr Macrae said you can do it with me. You can be naked as well as long as you stick to the rules. Do you want to?”
For a moment I didn’t grasp what she was suggesting. Then I stood and quickly undressed, pulling my boxer shorts off past my stiff cock. Her eyes widened as she saw it. “You’re a big boy, aren’t you? Bigger than my ex-husband. Much bigger.”
To have a woman as attractive as Gillian playing with herself for me was a huge turn on. She moved her legs apart further for me so that I could kneel between them and watch.
But I was careful not to touch her. That was against the rules.
Her hand began to move with more urgency, and my erection was rock-hard. I knelt above her and began to stroke my cock, making sure she could see everything. Her breathing became faster and she began to flush. “You like watching me, don’t you? Do you want to watch me come?”
She spread her legs still further and fingered her labia and clit while her other hand rubbed her nipples.
“Do you like me doing that? Are you pretending it’s your big cock in there instead of my finger?”
I was to find that when Gillian was excited, she lost her inhibitions and would tease me verbally as well as physically, often making the most incredibly erotic suggestions. I’m not sure which was more of a turn-on, her body or her ideas.
I picked up a towel to use when I came. Without stopping pleasuring herself, she gasped “Don’t come on the towel. Come on me instead.” I dropped it and canlı casino siteleri knelt up between her thighs, wanking hard over this sexy woman, both of us on the brink of orgasm. “God, yes, come on me,” she gasped.
Her hand moved even more rapidly and I spurted over her hand and bush. We both orgasmed together, all inhibitions gone.
* * * * *
Neither of us had expected things to go this way, but I was frankly flattered she had felt comfortable enough to perform such intimate act with me. Most of the girls I’d been with were shy about touching themselves, at least in front of a man. But Gillian was different. Despite the issues for which she was seeing her therapist, she was a mature, confident woman who know what she wanted, and loved to be looked at. She’d brought herself to orgasm in front of me, and enjoyed it. That was a very exciting combination.
Later, she told me she’d known perfectly well I could see her pussy while I had been massaging her that first time. She’d opened her legs both to see her effect on me, but also because she wanted to.
Throughout the whole session we hadn’t touched each other. But it had been one of the most erotically charged experiences I’d ever had.
* * * * *
As an ice-breaker, it’s hard to beat watching your partner come.
We took separate showers and got dressed again. Completely relaxed, we shared the rest of the wine and chatted about what we looked for in life and relationships.
During the following days I made myself come several times, just thinking about Gillian bringing herself to orgasm in front of me.
* * * * *
We scheduled the next session for the following Friday.
“I hope you were OK with how things went. I really hadn’t expected it to move ahead so quickly,” she said. “But it was a huge step for me – to be intimate again like that with a man, without any pressure. I’ve not had any kind of sex for a few years now, so Dr Macrae was really pleased. I told her all about it.”
“All about it?”
“Just the important bits. But – this is a secret between you and me – I didn’t tell her it was also a bit of a personal fantasy. To be watched by a man when I’m touching myself. My ex would just have told me to stop.”
“Well, I’m not complaining. I made a bit of a mess of your towels, though.” I said.
She laughed. “Seriously. I know I said some naughty things. But thanks for holding back. For being a gentleman. If you’d tried to push yourself on me it wouldn’t have worked.” She looked thoughtful. “Dr Macrae says men like you are quite hard to find. She wonders if you’d like to work with some of her other patients?”
“Only if they’re as good looking as you are.” She laughed again and topped up my glass.
“Well, think about it. She’s quite serious.”
Mentally, I filed the suggestion away. “So what does the doctor say we should do this afternoon?”
“Well. We can do the same again. If you enjoyed it. I know I did. Or we can go to the next stage.”
“You have to make me come.”
* * * * *
This time Gillian lay naked on the bed and told me what she wanted. There was a tube of lubricant on the bedside table. I squirted a blob onto two of my fingers. She spread her legs apart for me and I gently began to rub the lube between the pink lips of her cunt, teasing and stroking her. “Run your fingers up and down. God, that’s nice. Put a finger into me.” I found the right angle and began to finger-fuck her. She wriggled back in pleasure and closed her eyes. “That’s just right. Try two fingers. Yes. That’s just what I wanted.”
Then she began to make naughty suggestions; it turned her on and excited me. “Do you do this for all the mothers of your students? I think you should finger them as part of the deal. You can charge extra.”
“What if they’re not as cute as you?”
“Then I’ll stand in for them.” I slid my finger a little deeper into her. “Oh, God, that’s nice.”
Trying to anticipate her pleasure, I increased the rhythm, but she asked me to stop. “Anything wrong?”
“God, no! I was about to come. But we have to try something. Doctor’s orders.” She reached over to the bedside drawer and took out a vibrator. “What you’re doing is lovely, but can you use this on me? From behind?”
I grinned. “Yes, ma’am.”
“I love a man who follows orders.” She gave me a deep kiss, rolled over onto all fours and spread her legs to give me access to her pussy. I found the switch on the vibrator and began to run its bluntly pointed end up and down the lips of her cunt, carefully brushing her clit each time, sometimes thrusting into her, continually teasing her. She began to push her hips forward to meet my movements, her lovely breasts swinging as she did so. Gradually, she began to lose control, and after a few minutes she put her head down and thrust her hips towards me with growing urgency. “Fuck me with it. I want it in me. Fuck me hard.”
I pushed the dildo into her pussy at the same angle my fingers had used, this time with the vibration on full. She gave a wordless cry as she orgasmed, the muscles around her cunt and bottom contracting hard. I kept the vibrator deep inside her at full strength until the spasms of pleasure passed and she relaxed.
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