It was at breakfast that I first saw her.
I was on the second day of a week’s holiday in Maui, one of my favourite destinations. The resort hotels are well-situated and offer everything one could want. There are long stretches of golden sand bordering a sea rich in surf-topped waves. There are popular beaches, not too crowded but with enough people to provide a social setting. On the other hand, there are also several secluded little places hidden in between rocky outcrops where one can be totally alone and undisturbed.
The hotels offer an abundance of evening activities, including both formal and informal dining, as well as bars and nightclubs. For the romantically inclined there are delightful paths along the hills bordering the sea, with just enough lighting to see where one is going. For the more adventurous, a night-time dip in the waves is all one could desire before retiring to bed with the sound of the waves crashing on the shore to send one to sleep.
I had joined the breakfast buffet around the pool and was carrying my tray while looking for a place to sit down. It was quite crowded so would have to find someone who was willing to share their table.
I looked around and spotted a middle-aged couple on their own. The guy looked pleasant enough, but it was the woman who interested me. She was quite conservatively dressed, not showing acres of flesh, but unable to conceal what looked like a large bust on a good figure. She was very attentive to her partner, touching his hand and looking at him.
Now I like mature women, especially if they are married or in a long-term relationship. Fucking another man’s wife is a real turn-on, especially if it is the first time that she’s succumbed. I like the challenge of trying to seduce her, to make her forget her commitment and then give herself to me.
I approached them.
“Would you mind if I shared your table?” I asked, “there don’t seem to be any unoccupied ones available.”
The woman smiled at me.
“Of course not,” she said, “please join us.”
“Thank you so much,” I said, “I really appreciate it.”
I put my tray on the table and sat down.
“I’m Alan,” I said.
“I’m Jill,” the woman replied, “and this is my husband, Dan.”
I looked at her as she spoke. She was dressed in a cotton top decorated with flowers and a loose long wrap tied around her waist. I could see she was wearing a two-piece bathing costume underneath, so guessed that they would be enjoying the beach or the pool after breakfast.
Her husband was a good-looking man dressed in a typical Hawaiian shirt and shorts. He looked to be in his late forties or early fifties, around 180 or 190 lbs, and quite fit. He leaned forward and shook my hand.
“Pleased to meet you, Alan. You sound as though you come from England.”
“Yes,” I replied, “I’m from London. And you guys?”
“Oh, we’re from a small town in Michigan called Ludington, but you’re a long way from home, it must have taken you a long time to get here. What made you choose Maui?”
“Well,” I replied, “I actually know it quite well. I’m an information technology consultant and travel all over the world. I’ve spent a lot of time in the States and been all over the territory.”
“That’s a coincidence,” he said, “I’m also in technology.”
I glanced back at his wife. She seemed to be quite shy, not really engaging in the conversation, which I found strange as she had been the first to welcome me. I thought I should try to draw her out, and make her feel comfortable. If I could do that, it would give me an opportunity to engage more fully with her. I turned to her.
“And you, Jill, are you also in technology?”
“No,” she said, laughing, “I’m a teacher. I try to instil some knowledge into inattentive teenagers.”
“I’m impressed,” I said, “I used to teach programming to students at a polytechnic. It was quite challenging but at least discipline wasn’t an issue.”
“Oh really? You’ve been a teacher?”
“Only in the evenings and for two or three years. I was once asked to take a year off and lecture at the American University in Beirut but, to my eternal regret, I turned it down. It would have been such fun. Also, in the Middle East, they have special representatives in every classroom to keep discipline. They believe that teachers are there to teach, not to maintain discipline.”
“What a great idea,” she said, smiling at me.
The three of us carried on talking, covering a range of subjects. Jill became less reserved as we chatted, her body language more open. Finding something common between us had been fundamental in establishing that first link; my next step would be to build on that. I didn’t have a long time to do that, so would have to work hard. I had nothing against Dan, but I intended to fuck his wife before the week was out.
Eventually, I got up saying that it was time for me to go. I turned to Dan and shook his hand, saying that I was delighted to have met them, then turned to Jill and kissed each cheek in typical European style.
“It’s been a pleasure talking with you both,” I said, “I do hope that we see more of each other.”
She blushed and took her husband’s hand.
“I’ve enjoyed it too,” she said, “and I’m sure we’ll get together again.”
I left them and went to my room where I changed, getting ready for a little sunbathing. I put on a pair of Speedos. I like wearing those as they leave little to the imagination. I’m pretty well endowed and enjoy watching women (and sometimes men) looking at me surreptitiously. I put on a beach gown so that I could walk through the hotel, grabbed a book and went down to the hotel beach to get some towels and find a lounger.
There were already some people there, which suited me well as I like people-watching and imagining what they are doing. I could see young honeymoon couples discreetly exploring each other, middle-aged couples with the husband ogling young girls, and older single women looking out for a man to catch.
After a while I stretched out on my back and started to drift off to sleep, lulled by the sound of the waves in the background. I woke to the sound of a voice.
“Hello, Alan.”
I opened my eyes and sat up to see Dan standing in front of me, his wife just behind him.
“Hello Dan, are you guys coming to grab some sun?”
“No,” he said, “we were just walking down to the water to spend some time in the waves. Jill saw you lying there.”
“Hello Jill,” I said, “we’re meeting again rather sooner than I’d expected.”
She was carrying a beach bag and was no longer wearing any cover-up, just her bikini. I couldn’t help it. As my eyes looked her up and down I felt my cock stir and grow. She looked damn attractive. Her bust was certainly large, her breasts full. She had a little tummy, but nothing to detract. Her legs were well proportioned with a gap between them just under her groin. I imagined them wrapped around my waist as I fucked her.
“Hello Alan,” she said, “I hope you’ve put in some suntan cream. This sun can get quite fierce.”
“I have,” I said, “but now that you’re here could you perhaps do my back for me?”
“Of course,” she said, blushing, “give me the cream.”
There’s definitely some cream I’d like to give you, I thought as I handed her the bottle and leaned forward. She put some in her hands and started rubbing my back running her hands all over. They felt soft and sensual and once again I could feel my cock responding.
I leaned over a bit more, trying to conceal my growing erection. I glanced up at Dan and saw that he was staring at my crotch. Shit, I thought, I’ve blown it, I’ve turned an unplanned and fortunate encounter into a disaster. Then I saw him moisten his lips. Aha, maybe not, this might actually be more interesting.
Jill finished what she was doing and gave me back the cream before joining her husband.
“Thank you so much,” I said.
“You’re welcome,” she replied.
I leaned back on my elbows and watched her face. I saw her eyes widen as they strayed towards my crotch. Her cheeks turned red and her lips parted as she drew in her breath and stood there, immobilised.
“We should go now,” said Dan, “enjoy the sun, Alan,” and grabbing his wife’s hand, led her away. I watched them talking as they walked off and wondered whether they were talking about me. Judging from what I had seen, I might be successful and perhaps quite quickly.
I lay back enjoying the sunshine and thinking about how I could move to the next level. After a short while, I drifted off to sleep again.
I spent most of the day at the beach soaking up the sun and occasionally running into the sea and enjoying the waves until finally the sun was low and I decided to go and wash and change.
I showered off the sand and sunblock, had a shave, and changed into a shirt and slacks before heading downstairs. I wanted to walk to the top of a small cliff that dropped down to the sea where I knew that the hotel had a late afternoon ceremony. The path would be lit with fire lamps and a man would walk up it before climbing onto the top of the cliff and then diving into the sea.
I left the hotel and walked up the path to the viewing area to find quite a number of people there and, to my delight, saw that Dan and Jill were amongst them.
I went up to them and shook Dan’s hand and kissed Jill on both cheeks as I had done that morning. Dan was dressed similarly to me; Jill was in a light blouse and skirt. The top two buttons of her blouse were undone, giving a glimpse of cleavage.
“Hello you two,” I said, “You should enjoy this, it’s a really good thing to watch.”
Soon we heard the sound of drums and watched as a muscular man, his body oiled, ran past us and up the path to stand on top of the cliff. He stood there for a while and then executed a perfect dive into the water, which must have been some 50 feet below. We all held our breath until we saw him surface waving his arms. Everyone clapped.
“Let’s have a look at the bar here,” said Dan, “would you like to come with us, Alan?”
“Thank you, Dan, that’s most kind. Yes, I would love to join you.”
He put his arm around his wife’s shoulders as they led the way. I followed them, watching his wife’s butt and thinking how I would enjoy undressing her. My cock jerked.
The bar was outside on the edge of the beach. It was fairly basic but quite romantic being so close to the sea. There were a number of chairs for sitting at the counter, and a few benches looking out to the sea.
“Jill, you and Alan go and find a bench while I get the drinks. Jill, what would you like?”
“I’ll have a wine spritzer, thank you,” she said.
“And you, Alan?”
“A glass of red, thanks,” I replied, then turned to escort Jill to a bench, putting my hand low down on her back. I could feel her muscles ripple as she walked. For a moment I considered feeling her butt, but that would have been premature.
We found a bench and sat down. She crossed her legs. I sat as close as I could without making her feel uncomfortable and then rested my arm on the back of the bench behind her.
‘It’s beautiful, isn’t it?” I said, “so peaceful and away from the pressures of life.”
She leaned back and I felt her shoulders rest against my arm. She must have felt it too but didn’t move back.
“Yes,” she said, “I feel very relaxed here.”
Just then Dan arrived with the drinks and handed them out before sitting down. Strangely, he sat next to me, not his wife.
“So, Alan,” he said, “what do have planned for tomorrow?”
“I think I’ll spend some time exploring the beach,” I said, “I like spending time away from the crowds and finding secluded places where I can be alone with my thoughts.”
“Ah,” he said, laughing, “I bet you want to get an overall tan.”
“No,” I said, “too much danger of getting sunburnt danger in places I rather like to keep unharmed, but I do like swimming in the nude. It’s really quite liberating, not to mention erotic.”
Jill shifted herself, uncrossing and recrossing her legs. Dan laughed.
“That sounds like fun. I might join you.”
I’d far rather his wife joined me, but couldn’t say that. Then suddenly he got up.
“I’m going to book a table for dinner. Would you like to join us?”
“Are you sure?” I said, “I really don’t want to intrude.”
It was Jill who answered.
“You won’t be intruding. We’d love you to join us,” she said.
“Very well then,” I said.
“Ok then, finish your drinks. I’ll wait for you in the hotel lobby.”
He went off, leaving us sitting together on the bench.
“Do you really like swimming in the nude?” Jill asked, “aren’t you worried someone might come by and see you?”
“No, I’m not worried,” I answered, “I like my body. I think it’s in good shape and I’m not embarrassed by any of its bits. I don’t mind who sees me.”
“I wish I were like you,” she said, “I’m far too shy to do that.”
“Why on earth are you shy?” I said, “you’re a lovely person. You’re interesting and intelligent and so very thoughtful. And you are damn attractive. I’ve seen the way men look at you.”
She turned and looked at me.
“Do you really mean that?”
“Yes I do,” I said, and kissed her on the lips before getting up and offering her my hand.
“Come on, we better go back.”
She took my hand and got up. I put my arm around her waist as we walked along the path, feeling her pelvis move, when suddenly she stopped.
“You’re a very easy man to be with,” she said, turning to look at me, “you’re thoughtful and considerate. I feel very comfortable with you.”
I looked at her, resisting the impulse to kiss her passionately. My cock was now feeling uncomfortably constrained and I would have loved her to release it. I was sure that I would fuck her in the next few days, but I knew I had to take this at her speed. I was also pretty sure that her husband wouldn’t mind; the way he left me alone with his wife certainly seemed to indicate it.
“I’m delighted,” I said, “I feel very comfortable with you too.”
We resumed walking but this time I held her a bit higher, just under her bust. The movements from walking meant that my hand brushed against her breast from time to time.
By the time we arrived at the lobby I was really quite aroused. We looked for Dan and spotted him on the far side, so went over to join him.
“They’re ready for us now,” he said and led the way to restaurant.
We were shown to our table, where he and Jill sat down next to each other with me sitting opposite Jill. The waitress arrived and asked whether we would like some drinks.
“I think we should have something local,” I said, “what about a Mai Tai?”
“Oh, I’m not sure about that,” Jill said, “I don’t really drink very much alcohol.”
“We’ve got to enjoy the local produce,” Dan said, “you can always leave it if you don’t like it.”
“Alright then,” she said, “I don’t want to be the odd one out.”
Dan ordered the drinks. I hoped his wife would drink hers as they are quite strong and I reckoned it might weaken her defences.
The waitress returned with our drinks and the menus and then left us while we went through them, discussing what we would have. I noticed that Jill seemed to enjoy her Mai Tai. After a while the waitress returned and took our orders.
Our conversation during the meal was quite animated and never stopped. Dan was a good raconteur with a naughty sense of humour, and good fun to be with. I noticed that Jill was getting a little flushed as the alcohol took effect on her, so moved my legs forward, placing one between hers just nudging her.
“That’s a lovely ring you’re wearing,” I said, “can I see it a bit closer?”
“Sure,” she said, holding her left hand towards me. I took hold of it in my left hand, my fingers underneath and in her palm. She was wearing a diamond engagement ring together with a plain gold wedding band.
“That’s a beautiful engagement ring,” I said, “it has a wonderful sparkle.”
I stroked my fingers along her palm, thinking how her rings would look on her as she wrapped her fingers around my cock and felt her squeeze her legs around mine. I was definitely making progress.
“I can remember putting it on her finger and thinking the same thing,” said Dan, but I noticed that he shuffled in his seat.
We finished our dinner and I called for the check, insisting on paying. They both thanked me and we all got up. As we left and walked through the lobby, we heard the noise of the nightclub.
“Oh Dan, let’s go for a dance,” Jill said, then turning to me, “do you like to dance, Alan?”
“Yes I do,” I said, “I’m game.”
So we walked over to the entrance to the night club and waited to be shown to a table. Eventually, we were shown to a booth. Dan ordered some more Mai Tais, and then took Jill’s hand and led her onto the dance floor.
They really danced very well together. Jill was energetic in her movements with Dan leading her steps. I thought that she looked damn sexy.
They returned to the booth after four numbers. Jill slid along the seat and Dan sat next to her. I noticed that she was quite breathless. I also noticed that another button of her blouse had opened and that the top of her bra was showing.
After a while I asked Dan whether he would mind if I danced with his wife.
“Not at all,” he said, “if she’s happy to dance with you, so am I.”
“I would love to dance with you,” she said.
I stood up and held out my hand as Dan slid off the bench so she could get out. She took my hand and we went to the floor.
Dancing is an excellent way to establish physical contact with someone and creates an intimacy that allows you to enter a bubble with your partner, not aware of others. And that’s what happened. We twirled each other around, we touched each other everywhere, we looked into each other’s eyes.
After a few numbers, the atmosphere changed. The DJ put on a slower number and dimmed the lights. I looked at Jill then put my arms around her, my hands around her waist, and pulled her towards me. She moved in and out her head on my shoulder.
As we danced together slowly, I moved my hands lower to hold her buttocks and pulled her towards me. My cock was by now erect and pointing upwards as I rubbed it against her stomach, and that’s when I felt her rubbing back.
She lifted her head from my shoulder and looked at me, her eyes dreamy.
“That feels rather good,” she said, then moistened her lips.
I looked into her eyes and saw no hint of reticence or fear and knew that it was now no longer if, but when. I was definitely going to fuck her, the only questions were where and when.
I danced us round until we were quite a distance from her husband with other couples obscuring us. I was pretty sure that he wanted me to fuck his wife but didn’t want to take any chances and risk a fight.
I moved one hand up to the small of her back and the other between us so that I could reach her breast, then kissed her, nibbling her lips with mine. She kissed me back, probing my mouth with her tongue as I fondled her breast through her blouse. It felt magnificent, firm and full and big with her nipple hard and sticking out. My cock jerked against her stomach.
Then the DJ stopped the music and announced a break. We stepped apart and walked back to the booth to find Dan talking to another man. He broke off their conversation and turned to us.
“Did you have a good time?” He asked us.
“Yes I did,” I replied, “Jill is an excellent dancer. I really enjoyed myself.”
“You’re pretty good yourself,” she said.
“Well sit down and recover yourselves,” he said, “I’m just going to the little boys room.”
Jill sat down and slid along the bench. I decided to sit next to her and put my arm around her shoulder. My hand dangled down over her breast and I allowed my fingers to caress it. She kissed me gently.
“Not now,” she said, “perhaps another time.”
Dan returned but didn’t sit down.
“Time to go to bed,” he said, “I’ve paid the check.”
“Thanks, Dan,” I said, “and thank you Jill for a lovely evening. I’ve really had a great time with the two of you.”
We left the night club and I went to my room to shower and get ready for bed. I felt the evening had been a huge success and was looking forward to the next step.
**********
The next morning I woke quite early. I got dressed in shorts and a shirt. I didn’t bother with a swimming costume as I planned to go to a secluded cove and swim in the nude. I packed a costume in my beach bag, though, just in case as well as sunscreen, a couple of towels, and a book.
I went down for breakfast. The buffet was relatively empty as it was quite early, so I was able to have a table looking out to the sea. After breakfast, I returned to my room to fetch my beach bag, and then left for the beach.
I walked for a long time along the beautiful golden sand, lost in my thoughts. I wondered when I would next see Jill and what would happen. I must have walked a mile before I found what I was looking for, a small cove with rocky outcrops on each side.
I put down a towel and sat on it, looking at the sea. What a lovely place this was, so beautiful and peaceful, yet with an unseen force in the waves. I sat there for a long time, just listening to the waves crashing, before taking off my clothes and walking into the sea.
There’s nothing quite like feeling the waves lap against your body as the waters rise up. It’s a feeling of complete freedom, nothing between you and the world.
I stayed in the sea for a long time, jumping waves, swimming, body surfing, and just floating on my back until the sun was higher in the sky and I needed to put on some sunscreen. I went back to my towel and applied the cream liberally, then picked up my book and started reading.
Sometime later I noticed a figure in the distance walking on the sands towards me. I draped my other towel over my lap as the figure got closer when I saw that it was Jill. I wasn’t that surprised as I’d told both Dan and her more than once what I was going to do today.
It wasn’t long before she arrived and stood in front of me. She was in a floral bikini and carried a large beach bag.
“Hello Alan. Do you mind if I sit here?”
“Hello, Jill. Of course not,” I replied, “I’d really enjoy your company.”
She took a towel out of her bag and spread it on the ground next to mine, then sat down on it facing the sea.
“It’s a beautiful spot,” she said, “an azure sea with rolling waves and no one else to disturb the harmony.”
She turned to look at me.
“I enjoy being with you,” she said, “I feel relaxed and at ease.”
I turned on my side and, leaning over, kissed her, my tongue licking her lips. She opened her mouth and soon our tongues were intertwined, dancing with each other, our lips locked together. We kissed for a long time before breaking off and looking at each other.
“I think you’re a bit overdressed for this part of the beach,” I said, pulling her close to me and unfastening her bikini top.
She put her hands over her breasts, holding her top against her, still looking at me, then took them away and let it fall.
This was the first time I had seen her breasts uncovered. They were magnificent, so full and firm, with an enticing cleavage. Her areolae were large and dark pink, surrounding large erect nipples that stuck out, begging to be sucked. I felt a surge in my cock.
“My God, Jill,” I said, “your breasts are absolutely stunning.”
I reached out and put my hands over them, feeling them, then traced my fingers around her nipples. She sighed and thrust herself forward, as I played with her nipples between my fingers, rolling them, squeezing and pulling.
Then I noticed her eyes drift downwards and then widen. My towel had slipped off my waist when I had turned, and my erect cock was clearly visible. I reached for the towel and started to cover myself, but she put her hand over mine to stop me.
“Leave it like that,” she said.
I watched her face as she stared at my cock, transfixed. Then she seemed to come to a decision and reached forward to touch it, her fingers stroking my shaft then rubbing over the head.
“It’s beautiful,’ she said, “you have the most beautiful penis I’ve ever seen.”
My cock gave a little jerk as she said that and a few drops of precum dribbled out as she carried on feeling it. She lifted it up and curled her fingers around the shaft then squeezed before letting go.
“It’s big,” she said, “much bigger than Dan’s. Bigger than any I’ve seen.”
“How many lovers have you had?” I asked.
“Only one, really. The man who took my virginity, the man I married, Dan. Others have tried to seduce me, but I haven’t let them although I’ve seen some of them naked.”
“Would you like to feel another penis inside you, one that was different?”
“Yes, I would. I want to know what it feels like, but I’m scared, scared of being hurt, scared of liking it, scared of being unfaithful to my husband.”
“Don’t be scared,” I said, “follow your feelings and don’t overthink things.”
I knew she would come to the right decision, but she needed time to rationalise it. She wanted to know what a big cock felt like inside her. Most women have similar desires coupled with concerns – whether it will hurt, whether their vagina will be able to accommodate it and, if it does, whether it will return to what it was. Inevitably, however, their curiosity and wish for the experience overcome their fears.
She looked at me, then touched my face, stroking my cheek.
“You’re a sensitive man, Alan, sensitive and understanding but also very attractive and masculine. That’s an unusual mixture.”
She moved her hand to my chest with her fingers spread and stroked gently, pulling her fingers together, then traced them downwards along fingering the line of hair that led down to my pubic hair.
“Mmmm. A pathway to promised pleasures,” she said, smiling.
There was no doubt about it, I was definitely going to fuck her. She wanted me. Her cunt that had only known her husband’s cock was going to be filled with mine and I knew that once I’d been there, she’d want me again. The only remaining question was when.
“Stand up, Jill,” I said, “I want to look at you.”
She got up without hesitation and stood in front of me. I also got up and stood in front of her, my cock standing out. Her body looked so enticing with her large breasts and alluring figure. I noticed that her bikini bottom had a wet patch spreading through the gusset.
I stepped forward and kissed her then put my hands on her buttocks and pulled her in towards me, my cock trapped between us and squashed against her stomach.
We kissed passionately as I felt all over her butt. I pulled her cheeks apart, searching for her slit with my fingers as I slid them underneath the hem of her bikini where it clung round the top of her legs. She was really quite wet and slippery and my fingers soon found her labia.
I felt her squirm and push harder against me as she thrust her tongue into my mouth. I was now able to insert a finger between her labia, opening them. She responded by reaching for my cock and stroking it. I broke our kiss and took my hands out of her bikini then hooked my thumbs in the top and slowly slid them down.
Jill looked at me as I removed the last item of clothing, the last barrier to my cock entering her cunt. Her bush was fabulous, a lush forest of black hair surrounding her pink vulva.
“You are so sexy,” I said, “I love your pubic hair, shrouding your vaginal mystery. Are you ready now?”
“Yes,” she said quietly, “I’m ready. I want you to make love to me, but not here. It’s too public. Can we go back to your room?”
I thought before answering. I knew I could push her to fuck me now, but she wouldn’t relax fully. If we waited, perhaps she’d get nervous again. Oh well, if that happened I’d just have to start again.
“Of course,” I said, “let’s get outer things together and walk back.”
Then a thought occurred to me. If there were any unforeseen delays, she should have something to keep her attitude positive.
“Have you got your phone with you?”
“Yes.”
“OK. Let’s swap numbers so that we can easily keep in touch.”
“Oh that’s a good idea,” she said, her face bright.
We took down each other’s numbers and I sent a text to confirm it was all working. Then we put on our swimming gear, picked up our things, and walked back to the hotel, hand in hand
As we neared the hotel beach, we let go of each other’s hands. Just as well as when we were on the path to the lobby, we ran into Dan.
“Ah,” he said, “I see you two met. I told Jill that you had gone for a walk on the beach.”
“Yes, I bumped into him about a mile away,” said Jill, blushing “it was a beautiful place with the waves of the sea crashing in the background.”
“Sounds idyllic. Alan, would you like to join me for a drink? I need some advice and would value your opinion.”
“Sure,” I said, “let me drop off my things and have a quick shower. I’ll join you at the beach bar.”
As I showered, I wondered what he wanted to talk about. Was he worried about Jill’s growing interest in me? After the shower I dressed in a new shirt and shorts and went down to the bar.
Dan was already there drinking a beer. I ordered a gin and tonic.
“Let’s go and sit on that bench over there” he said.
We walked to the bench and sat down.
“I saw what happened,” he said, “I knew that Jill wanted to find you, so I followed her at a distance. I watched the two of you from behind the rocks.”
He was looking at me, but not in anger. Instead, he seemed almost aroused.
“Did you like it?” I asked, “or were you disappointed?”
“Both,” he said, “I like to see her get aroused but I wanted to watch her enjoyment as you fucked her, and you didn’t. Why did you stop?”
Wow, I thought, although I wasn’t surprised as I had suspected he wanted this, it was another matter to hear it so bluntly.
“Hell, Dan, are you sure you want to hear this?”
“Yes,” he said, “I do.”
“I stopped because your wife wasn’t comfortable in public and I didn’t want to pressure her. She told me that she has only ever had two men and that for the last twenty-five years she’s only known you. I want her first time with me to be special, to make sure that she never forgets it and will always want more.”
“I understand,” he said, “but I want to watch.”
“No, Dan, that won’t work. Or at least it won’t work if she knows. She has to be completely relaxed and not worry about anything. After that she won’t care.”
He was quiet after my response as he considered what I had said. Then my phone pinged. It was Jill.
‘Is everything alright?’
‘Yes, no problem.’
‘Good. When can we meet.’
‘Soon. I’ll text.’
“That was Jill,’ I said, “she wants to meet. Are you OK with what I said?”
“Yes,” he said, “go ahead. I’ll tell her I’m going out for a while.”
“Thanks, Dan. I will look after her. Give me your phone number so that we can stay in touch.”
He gave me his number and we exchanged a text for confirmation before I got up and left him, returning to my room. When I got there I texted her telling her to come as soon as she could. Twenty minutes later she was at my door. She was wearing a navy silk blouse with black slacks and looked absolutely fabulous. She’d clearly decided to dress especially for our liaison, and I wondered what she had on underneath.
I welcomed her with a kiss and asked her if she’d like a drink.
“Yes please,” she said, “some white wine would be good,” sitting down on the couch.
I poured two glasses and sat down next to her.
“Are you ready for this now?” I asked.
“Yes,” she said.
I put down my glass, took hers and put it down, then kissed her gently, my lips brushing hers.
“You have lovely soft lips,” I said, “they are very kissable.”
She held the back of my head and kissed me back, her hands stroking my hair. I licked inside her mouth, lifting her tongue with mine and licking underneath it. She murmured softly.
I put a hand on her breast, squeezing it gently and feeling it slip under the silky material of her blouse. I could feel her nipple, hard and straining against the material. She must be wearing a sheer bra, I thought. I pinched her nipple gently, rolling it between my fingers, and felt it grow some more.
I did the same with her other breast, my mouth still locked onto hers, and felt her wriggle. I broke our kiss and unbuttoned her blouse then slipped it off her. She was wearing a transparent bra with lace around the edge, her areolae dark pink and clearly visible as were her nipples which were pushing out the material. She looked incredibly sexy.
“Wow,” I said, “you look fantastic. Did you put that on especially for me?”
“Yes,” she said, “I wanted to look good for you.”
“Well, you’ve succeeded beyond imagination.”
I leaned forward again and kissed her eyes, then ran my tongue down the side of her neck before nibbling gently at the curve above her collar bone and then licking her shoulder. She was holding my head gently.
“Aaaah, that’s lovely,” she said.
I ran my tongue back up her neck and on to her ear, nibbling on her earlobe and then blowing softly into her ear. I felt her shiver.
I reached behind her and unclasped her bra then took it off and dropped it on the floor.
“God your breasts are beautiful.”
I sucked on one of her nipples, taking the whole of her areola into my mouth and flicking my tongue over her nipple. I felt her body tense as she tightened her hold on my head and she thrust her hips forward.
“Aaaah. Oh, that is really nice.”
I licked underneath both breasts then trailed my tongue downwards, probing into her navel, as I undid the top of her slacks and loosened her zip, then down until I encountered the beginnings of her pubic hair.
“Lift up,” I said, pulling at her slacks.
She lifted her hips and I pulled down her slacks taking them off each leg. She was wearing a thong that matched her now discarded bra. She looked fucking sexy. It wasn’t big enough to cover her bush, and anyway I could see it through the transparent material. My cock jerked as I looked at her and I could feel my precum seeping into my boxers.
“My God you’re gorgeous,” I said, pulling down her thong and leaning forward to push my face into her groin. I sucked her pubic hair, licking the skin underneath, as I moved down searching for her clit until I found it still encased in its sheath.
I tickled the top with my tongue, licking the small shaft, then round the side, pushing hard as I licked. She was pushing my head down onto her as she made little fucking movements, opening her legs wider.
“Oh yes, yes. Oh my,” she said softly.
I pulled her thong to the side and felt for her slit. I could feel her labia, wet and slippery. They were still clasped together as I ran my fingers up and down them searching for a little chink that I could explore.
She lifted her hips up, her feet braced on the floor, as I continued to play with her, thrusting herself into my mouth. I ran my tongue over the top of her clit and was delighted to find that the tip had emerged. She gave a jump and I felt her labia open a little as my fingers explored.
I moved my mouth down and licked her slit, which was now extremely wet with her juices running down her crack. I licked up and down, slowly parting her labia with my tongue and giving me access to her soft inner flesh.
Her labia opened some more and I was able to suck them into my mouth. They weren’t very large but were certainly sensitive as she was now moving around vigorously. I inserted a finger into her vagina. It was really tight, and seemed to suck my finger in as her muscles contracted and relaxed.
“Oh Alan, this is so, so good. It feels wonderful.”
I realised that it was going to take a lot more preparation for her to be ready to take me. I wanted it to be a perfect time for her with memories of pure pleasure and nothing else.
“I think we should move to the bed. It will be much more comfortable.”
I stood up and helped her off the couch. She stood up and I gave her a big sloppy kiss before leading her to the bed. She lay down on it on her back with her knees bent.
I pulled down her thong and slipped it off her legs. It was like a sodden rag. I pressed it to my nose, inhaling her scent.
“You smell so sexy,” I said, then grabbed some pillows and studied them under her butt before getting on the bed and kneeling between her legs and starting to lick her cunt again.
It wasn’t long before she was in the same rhythm again as I sucked her labia, drawing them out as much as I could while I fingered her vaginal entrance. My cock was now dribbling precum all over the place and felt like a rod of steel.
I stopped sucking her and, moving up a bit, pressed my glans on her clit then rubbed it from side to side, using my precum as lubrication. She gave a long sigh, her eyes closed, then opened them and gazed into my face.
“You are a lovely man,” she said, reaching up to stroke my face, “and you make love beautifully.”
“That’s because I have a wonderful woman to make love to,” I replied, “a beautiful, intelligent, sensual woman.”
I moved up the bed, my legs on either side of her body, trailing my cock over her, anointing her with my precum, before rubbing my glans on her nipples.
She reached up and fondled my balls, jiggling them around in my scrotum and then holding them.
I moved higher and rubbed my glans over her lips then felt her open her mouth and as her tongue came out and tickled my frenulum. I leaned over her and adjusted the angle so that she could take my glans in her mouth. Her lips slid over it and soon I felt the warm interior of her mouth, her tongue swirling around.
“Oh that’s nice,” I said.
“Mmmmmm,” was her response.
I could feel my precum pouring out and looked down to see her throat move as she swallowed. I wondered how deep I could get into her mouth, then discarded the thought. I wanted to try and enter her, so I pulled my cock out of her mouth and then lay down next to her, put an arm around her and rolled her over on top of me.
“Get on your knees,” I said.
She knelt on either side of me and I shuffled down until my head was under her cunt. It looked damn exciting. Her labia were open and I could see her pink flesh inside, glistening with moisture. Drops were forming at the base of her slit and dripping onto my chin. I lifted my head and stuck my tongue into her hole, lapping up her juices. Her hips jerked and she made little backward and forward movements.
“Oh Alan,” she said.
I carried on licking, sucking and swallowing as she sawed back and forth, then with a lay upward lick shuffled back up under her until my cock was beneath her cunt.
“Hold my penis. Rub the head against your labia and you’ll feel it gradually begin to move in. Don’t rush. Enjoy the feeling. You are in control.”
She reached down and took hold of my penis then brushed its head back and forth over her slit. It felt wonderful. She was so wet and, together with my precum, it slid easily against her folds.
I looked at her face as she was doing this, her eyes were closed and she had a look of concentration. Then I felt her press down and I felt my glans begin to slip between her labia, moving in slowly until it stopped against something tight.
“Don’t rush, Jill, just relax. We have all the time in the world.”
She leaned forward, adjusting the angle, and bringing her breasts within easy reach. I held one in each hand, feeling their heavy weight, then fondling them.
I felt her press down a bit harder on my cock when suddenly the head popped through her vaginal sphincter and began its journey towards her depths. It felt fantastic. That moment when the muscle relaxes and I break through to feel the walls of a vagina tickling my corona is one of the feelings I enjoy the most.
“Ooof,” she cried, then “Aaah.”
There was a look of both triumph relief on her face followed by a beaming smile.
“We’ve done it. You’re inside me,” she said happily.
I smiled at her. My glans felt warm and cosy and very sensitive. Most of my shaft was still outside, but I knew that before long it would all be inside her.
She sat up again and started to lower herself down very slowly. I saw her labia wrapped tightly around my shaft, getting dragged inwards, and thought that if they had a big cock inside them more often, they would soon enlarge.
After a while she stopped pushing down and leant forward again, resting on her arms. I felt her shuffle her pelvis and my cock sank in a bit further, my glans tingling as it rubbed against the walls of her vagina, forcing them apart.
She pushed down again and I felt her cervix brush my head.
“Aah,” she exclaimed, then pushed some more until I felt the back of her cunt and she stopped pushing.
“Wait a moment,” I said, “give your vagina time to adjust then we can try some more.”
She lifted herself back up and then leaned back with her hands on my thighs. We still had an inch or so to go. I clenched my pelvic muscles, making my cock expand and jerk.
“Oooo,” she cried, “oh please do that again.”
I did, eliciting another ‘ooooo’ and feeling her vagina clench. Then slowly my cock sank further into her until I felt her pubis on mine and our pubic hair enmeshed.
Again I waited while her vagina adjusted, then made my cock jerk. Another cry from her. I put my hands on her waist, feeling her pelvis, as I looked at this gorgeous woman sitting on me, my cock buried deep inside her tight cunt.
“God you look sexy,” I said.
She smiled at me and started to move. Her cunt was feeling a little looser inside now, although her entrance was still tight. I could feel her muscles rippling up and down my cock. My head felt tickled beyond and my nerves were on edge, but I had to control myself. I wanted her to climax first. After that, I was going to fuck her into another world, one where the only thing that mattered to her was my cock.
“Oh Alan,” she said, “this is amazing. My vagina feels so full of you, full of a living, powerful member throbbing inside me. I can feel your pulse inside me.”
I started to thrust up in time to her downward movements, then pull back as she went up, my cock head near her entrance. She was becoming much looser and felt more slippery inside.
“Oh god that feels good,” she cried, “oh my word,” speeding up and pushing harder until suddenly she pressed down hard and stayed still, her cunt pulsing around my cock.
“Aaargh,” she cried, “oh, oh, oh. Oh god.”
I felt her cunt clutching and releasing my cock, desperately trying to make me cum, then slowly relaxing. I watched her face, contorted in concentration, then slowly relaxing into a peaceful smile.
“That was beautiful,” she said breathlessly, “such exquisite feelings. You seemed to be touching me everywhere inside, stimulating nerves I didn’t know existed.”
“I’m pleased you enjoyed it,” I said, “I enjoyed being part of your pleasure.”
“But you didn’t climax,” she said.
“Don’t worry,” I said, “we’re not finished. Now let’s roll over, I want to be on top of you.”
I wanted to take her now. I wanted to dominate her, overpower her, make her mine.
She slowly rolled to her side, my cock still firmly embedded in her, then onto her back. I lay on top of her, her breasts squashed against my chest, and kissed her, my tongue playing with hers. Then I lifted myself up on my arms.
“I’m going to fuck you now, Jill, fuck you until you scream with pleasure. All that will think about is my big cock and how incredible it feels. You will feel like you’re in another world, a world where all that matters is your cunt and the pleasure it gets from my cock.”
She stared up at me wide-eyed, but her cunt gave her away as it twitched around my cock. I had deliberately chosen my words as I was sure that now she’d had a big cock inside her, she was ready to let herself go and enjoy exploring other men.
“Put your legs around me. I want to feel them holding me.”
She lifted her legs up and wrapped them around my waist, her feet on the small of my back.
I started to fuck her with long slow deliberate strokes, my cock deep inside and then almost all of the way out. I could feel her labia wrapped tightly around my shaft, moving in and out and my cockhead rubbing against her walls.
After a few strokes, I felt her move her hips and then felt her cunt tense around me. A few more strokes and she started to fuck me back. I speeded up a little and thrust harder. I could feel my cockhead sliding under her cervix and then banging into the back of her cunt, the anterior fornix.
She was panting now, her breathing heavy and making little noises with each thrust. I could feel her feet banging on my back as my buttocks rose and fell. Then I felt her hands on my forearms, rubbing up and down and then holding them.
“You’re right,” she said, panting, “I do want you to take me.”
I speeded up some more, pounding my cock in and out, my balls banging against her crack. Her cunt was now clamping and relaxing around my shaft as she worked her inner muscles. I could feel its warmth infusing my cock. My corona was on fire from scraping the walls of her vagina and my balls were tight against my shaft. I knew I was almost there.
She moved her hands to pull on my buttocks, trying to get me deeper.
“Cum in me,” she cried, “I want to feel you cum in me.”
I held my breath as I felt a wave of pleasure spread through my groin and the muscle at the base of my cock relaxed then tensed and shot a flood of semen up my cock to shoot out of the end and into her cunt.
“Aaaah,” she cried as my warm semen with its millions of sperm sprayed deep inside her vagina, flooding around my cock.
“Yes. Yes. Oh my God. Oh Alan, Alan,” she screamed loudly as I ejaculated again and again, pumping her cunt full of my DNA.
Her legs kicked against my back, and her fingers dug into my buttocks. Her cunt pulsed and sucked at my cock, holding it like a vice. I could hear the blood pounding in my ears and see flashes of light. It was one of the most intense orgasms I have known.
Then slowly I calmed down and my heartbeat slowed down. I sank down onto her and kissed her gently, brushing her hair off her face. She let go of my buttocks and stroked my cheek then ran a finger over my eyebrows.
“That was incredible,” she said, “feeling you ejaculate inside me was so overwhelming. My mind was full of an image of your penis invading my body and surrounded by flesh with semen spurting out of the end, but I felt your whole persona was in me, not just part of your body.”
“I’m glad you enjoyed it,” I said, “I did too. You are a marvellous lover, a very sexy woman who knows how to use her body to please a man.”
She blushed but looked pleased.
“Would you like to do this again?” I asked.
“You mean now? I don’t think I could.”
“No, not now,” I said, laughing, “another time.”
“Yes,” she said, “I definitely want to do it again, but what am I going to say to my husband?”
“Nothing unless he asks,” I replied, “and if he does you need to tell him that you have needs that he can’t satisfy.”
She looked troubled. I was still quite hard so I gave a little thrust to remind her how it felt having a proper cock inside her.
“Listen, Jill, you deserve to enjoy your femininity. You don’t have to be promiscuous, but it seems to me that you need something more than Dan can provide. For the moment you can get that from me, but when you get home you’re going to have to work out what to do.”
“I guess so,” she said.
“Good,” I said, “let’s see how it works out. Now I’m going to pull out and we’re going to make an awful mess for housekeeping.”
I sat back on my haunches and pulled my cock out slowly. Her labia were still tightly wrapped around my shaft and were dragged out with it, reluctantly allowing it to slip from their grasp.
An absolute flood of semen followed, draining out of her cunt and down her crack onto the bed. I leapt up and went to fetch a towel then returned, picking up my phone on the way.
Her cunt was still wide open, her labia apart and looking and looking loose and ragged. There was semen everywhere, glistening on her.
“You look like you should,” I said, “like you’ve had a really good time. I’m going to take a picture so that you can see.”
I took a couple of shots. I would send them to her husband later so that he could see what his wife’s cunt looked like when she’d had a proper cock inside it. I was sure he would masturbate while looking at it.
“I feel so empty,” said Jill, “like part of me is missing.”
“You can have that part again any time you want,” I said, “just tell me. But what about me? Can I tell you when I want you?”
She thought about that before replying.
“Yes,” she said, “I will be there for you if you want me. It may take some organising, but I’ll be there.”
And that was that, her cunt was mine. What a shame she lived so far away. Still, I had her for the rest of my holiday. She would be available whenever I wanted.
She got off the bed, holding her hand under her cunt.
“I think I should take a shower and then go back to my room. Dan is probably back and will be wondering where I am.”
She went into the bathroom and I heard the shower running. I picked up my phone and sent 3 messages to Dan.
‘Your wife loved my cock. She wants more.’
‘She screamed my name as she orgasmed,’
‘This is what her well-fucked cunt looks like’
Then I sent the two pics.
‘OMG. I’ve never seen her so wide.’
‘I didn’t know you were going to cum in her.’
‘Of course I was going to cum in her.’
‘Did she know?’
‘She begged me to do so.’
‘What now?’
‘She wants me to fuck her again.’
‘Where is she?’
‘In my shower. She’ll be back in your room soon. Make sure you’re not there.’
‘OK. Can we meet?’
‘Yes. In the beach bar in thirty.’
‘Great.
I put down my phone.
Jill emerged after about ten minutes looking fresh and clean. She put on her bra and then her thong which was really like a wet rag, so not much use, before retrieving her blouse and slacks.
“My semen will be running out of you for a few hours,” I said, “so it’s probably worth putting on some more substantial panties.”
“Oh I will,” she said, laughing, “but I’ll also enjoy feeling it in my panties as it will remind me of our time together.”
I pulled her close to me and kissed her. Our mouths locked together passionately, and then she broke it off and held my penis briefly before walking to the door.
“Until next time,” she said and left.
Well, she’d been a magnificent fuck. I’d enjoyed myself immensely as had she. There were no longer any barriers to surmount. She had discovered the joy of a big cock and wanted more. I had another man’s wife as my sexual partner for my holiday and, even better, he knew about it. The next step was to find out whether he could be included.
I went into the shower to get myself cleaned up for meeting him.
