After my relaxing trip away with my family I settled down at home and a week later I was sat at home when I received a text message from Nikki. I read it, and she said that she had arranged to meet Tom, the guy that she had been communicating with since our last meeting.
As I read her message, I wondered why she had told me about it, what did she want from me? I replied that I was pleased and wished her well and told her to relax and just enjoy herself.
Her next message said simply, ‘call me?’
I shrugged and called her. It turned out that she was incredibly nervous and was wondering whether to go through with it or not. I assured her that she would enjoy herself if she let herself relax. Her date was in a couple of days, and she had agreed to meet him in a hotel on the edge of the major town nearest to her village.
We talked for a while, I told her about my trip away with the family, and she was surprised that I had told my daughters about her. I assured her that I hadn’t disclosed the website where we had met, nor, the nature of our friendship. I could sense her nerves as we talked and did my best to relax her, and by the time we said goodnight, she seemed to be in a better place.
The next day was Friday, and after a light lunch, at what was my wife’s favourite pub located by one of the locks of the canal that ran through the village I headed home.
I thought about Nikki, and her date with Tom the following evening and I found myself back on the website. I read the messages that had been left for me from a surprising number of women who had responded to my profile. I was genuinely surprised that so many women were interested in me, and by the number who were a lot younger than me.
As I read down I noticed one from a woman called Helen. She had been one of the first to respond to me when I joined, and we had shared a few messages since then. When I read her latest message she said that she felt that she was ready and asked if I was still interested in meeting her. I checked her profile page to remind myself of her. She was sixty, a widow of four years after being married to her husband for thirty years. She was an attractive woman, her silvery-grey hair hung down to her shoulders, and she was around five-foot-four and quite slim.
I thought about it for a moment and then responded. I said that I was still very interested in meeting her and if she wanted to get together, I was free the following evening.
I waited, and waited, she took five minutes to reply, and when she did, it was positive, she had agreed to meet me the next evening. She had sent me her mobile number so I called her and we talked for a while before I focussed things on the matter at hand.
“Okay Helen, about tomorrow? Where do you want to meet? I asked.
She hesitated and asked me how I felt about going to her house. This surprised me, but, she explained that she would feel a lot more comfortable at home. I questioned her and asked her if she was sure. She said that she was, but had one request.
“Could we do it in one of the spare rooms?”
She wasn’t comfortable having sex in the bed that she had shared with her late husband. Of course, I agreed, I understood and told her so. Before we hung up I asked her about condoms. She said that she would leave that decision down to me.
“If you are okay not using one then that is fine with me James, I understand that you might be concerned.” She said.
I assured her that I wasn’t concerned about her, as long as she was happy. She said that she preferred not to use one as she could sometimes be quite dry and she worried about it affecting the experience.
After we had finished talking, I sat back and began to look forward to the following evening. As I did, I thought about Nikki, and for a moment I wondered if my decision to meet Helen had anything to do with the fact that she was meeting Tom that same evening. I convinced myself that I was being silly and reminded myself that it was me who had pushed her to contact Tom in the first place.
The following day I found myself feeling surprisingly nervous as I got myself ready to leave to go to Helen’s. I checked myself in the mirror for one last time and sighed.
“Look at you! You’re going out to have sex, you should be on top of the world!”
I rolled my eyes at myself, the guy in the reflection was right, I should be excited, and, I was, but I knew that something was niggling me at the back of my mind. I looked myself over one last time then turned and walked out of the bedroom.
I pulled up outside of her little cottage and turned off the engine. I looked towards the window that faced out onto the road, there was a light glow emanating from the room and I imagined Helen sat nervously on a sofa waiting for my arrival.
When she opened the door I could see how nervous that she was, and as we hugged and I kissed her cheek I could feel her trembling. I smiled and brushed my fingers across her cheek.
“It’s lovely to finally meet you, Helen. I’m sure that we will have a great time, just try to relax.” I said softly.
She nodded and stepped back to let me in. I walked past her, and as we walked into the lounge, I saw that she was wearing a simple, yet elegant, sleeveless burgundy dress that ended just above her knees. Around her neck, she wore a single strand of cream pearls and I noticed that she still had her wedding and engagement rings on her finger. As she walked ahead of me I looked down at her legs which were covered in sheer stockings or tights, I hoped the former, and I looked forward to finding out which.
She offered me a drink, I took a soft drink and she took a glass of red wine. I noticed that the glass that she used had a trace of wine in the bottom, she had been drinking before I arrived.
We sat and chatted, it was all very friendly, and it was clear that she was nervous and wasn’t sure about how to take it forward. In the end, I took control of the situation. I took her almost empty glass and placed it on the coffee table in front of us and slipped my arm around her back. She faced me and I looked into her eyes.
“I think we should get started, Helen,” I whispered.
She didn’t reply, her eyes blinked and she nodded. I leaned forward and kissed her.
She let out a soft moan which lengthened as I pulled her close to me and slid my hands around her back. I pushed my tongue at her lips and the parted to allow it inside her mouth where I sought hers out and began to toy with it.
She began to respond, her hands slid up my arms and gripped them as I leaned her back into the sofa and let my fingers caress and stroke across her neck. I parted and stared into her eyes and smiled.
“That was nice.” I sighed.
She nodded. “Very.” She replied.
We kissed again, and I let my hand fall and stroke across the back of her dress. I slid it down across her bum and as I did, I felt the unmistakable outline of suspenders. Jackpot! Suspenders are my favourite thing.
I could feel her beginning to relax, and as she responded to me I suggested that we move to the bedroom. Her face was flushed as she looked at me and nodded. “Okay,” She replied. I stood and held out my hand. She took it and I helped her to her feet and into my arms. We kissed and as we broke she looked into my eyes. I traced my finger across her lips.
“I’ll be gentle,” I whispered.
She bit her lip.
“What if I don’t want you to?” She replied.
I must have looked confused, she rolled her eyes.
“To be gentle.” She smiled. I raised my eyebrows, ‘this might get interesting’, I thought.
In the bedroom, she seemed to get more nervous. I took her into my arms and held her close as I kissed her and ran my hands down her back. She slid her hands around my neck and hung onto me as we kissed passionately and when my hands reached her bum, I pulled her onto me and she groaned when she felt my hard cock press into the belly. At nearly nine inches taller than her at six-one she had her head tilted up as we kissed and her arms wrapped around my neck as she started to push back at my tongue which had once again invaded her mouth.
I reached behind and started to slowly slide the zip of her dress down, this seemed to spur her on and she increased the intensity of her kisses. With her dress unzipped, I slid my hands inside and felt the warm, soft flesh of her back. She moved against me when she felt my fingers on her skin and her hands dropped and her fingers started to tug my shirt from my trousers and she began work on the buttons. I smiled to myself, she was coming out of her shell, her instinct was taking over.
With the last button of my shirt undone, she pushed her hands inside and pushed it from my chest, she helped it down over my arms and when it fell to the floor I was stood, bare-chested before her. She stared and let her fingers slide across my chest, I’m not a muscular man, but I try to take care of myself, and I’m happy with the way my body is. And, judging by her response, so was Helen.
As she caressed her fingers over my chest I helped the straps of her dress down and over her shoulders. She lowered her hands to facilitate me in removing the dress, and I stared as it slid down her body to reveal a cream, lace-panelled bra, and a pair of cream, French-style, silk, cami-knickers. I must have stared too much, she asked me if everything was okay.
“Okay? You look fantastic Helen. I love those knickers, and oh god, the suspenders! I’m in heaven.” I said
She grinned as I let my fingers slide across the front of her bra and I felt the hard nipple of her breast. I hadn’t been able to judge her size in any of the photos that she’d sent, but she must have been at least a C-cup, and I could see her dark nipples through the sheer material of her bra.
I smiled, “I feel a little over-dressed.” I whispered.
She grinned and got the message and began to unfasten my belt, and then started on my trousers. Soon they were opened and unzipped and she was pushing them down over my hips. When they got to my knees she was bent over a little and her face was level with my crotch when she freed my boxers and my hard cock poked up and pushed the material out into a tent. She stared at it for a few seconds then pushed my trousers to the floor and I stepped out of them and pulled her to her feet.
We kissed again and she could feel my hard cock pressing into her body. I brushed my fingers across her face.
“Okay, Helen. Here’s the thing. I’m here to help you enjoy yourself, I want you to be relaxed, and, I want you to tell me everything that you want to try tonight. don’t be embarrassed, we are both adults, and, if its too outrageous, I’ll tell you” I said, joking.
She smiled and bit her lip. She had already told me that she wasn’t that experienced, sexually. Although she had loved her husband dearly, sex hadn’t been a huge part of their marriage, not for him anyway, and when they did make love, it was usually straight-forward, with little experimenting or variety.
I held her close and ground myself against her, just to make sure she knew that she had me aroused.
“I remember you telling me that your husband didn’t much like oral sex,” I whispered.
She nodded, her eyes glued to mine. I smiled.
“Well, I love it. So, why don’t we start with that? We can either do it individually or get into a sixty-nine?”
She looked unsure, I stroked her face.
“Tell you what, why don’t you start? We will take it from there.” I whispered.
She nodded and bit her lip, she looked so sexy when she did that.
“As long as you tell me if I do it wrong.” She sighed.
I smiled. “You’ll be fine.” And I led her to the bed.
I lay down on my back, propped up on the pillows against the headboard and she knelt beside me looking nervous. I smiled.
“You’ll need to get rid of my boxers. “I said softly.
She nodded and started to slide them down my thighs. I lifted my bum from the bed to aid her and when she exposed my cock it sprung out, she jumped a little as it flicked up and stood proud, pointing at her, and already leaking pre-cum.
She dropped my shorts on the bed and stared at my cock.
“Hold it. It won’t bite, as long as you don’t.” I said, trying to relax her.
She reached out, her fingers trembled and I moaned when I felt them slide around my cock and gently grip it. She had a lovely soft touch, she may have not done it much, but she knew how to hold it and I stared as she moved her fingers along the shaft and started to stroke it gently.
“Hmmm, of god, Helen, that feels so good. “ I sighed.
She smiled and continued to work her hand up and down, her attention focussed on the thick head which glistened with pre-cum. I stroked my hand over her head and, applied a little gentle pressure to the back.
“Why don’t you try taking it in your mouth?” I whispered.
She licked her lips, and staring at the head she slowly lowered her head and I watched as her hair fell forward, obscuring the view. Then, I moaned when I felt her warm, wet lips slide over the head of my cock and down onto the shaft, then she closed them around it and I felt the head slide further into her mouth until I felt her tongue slide across the tip.
“Oh god!” I moaned, and slid my fingers through her hair and pressed her head down gently.
“Shit! That’s fantastic!” groaned.
Then, she started to move her head up and down, and as she did, her tongue, whether on purpose or not, began to slide along the shaft, licking it and as she pulled back she let the tip of her tongue flick across my head of my cock. My whole body tingled as she worked my cock like an expert. She’d only been at it for less than a minute, but it was turning out to be an awesome blow-job. I laid my head back and enjoyed the experience, my hand rested on the back of her head but I didn’t need to guide her, she was doing great, and she seemed to be enjoying herself.
I watched as her head bobbed up and down, her silver hair had flopped forward and I could feel it brushing against my skin, which only enhanced the experience for me. I wondered whether she had done it like this for her husband, if she had, I couldn’t possibly see how he wouldn’t have enjoyed it, or wanted it more often.
As she got into it I started to push back at her, and occasionally I pushed too far and she’d gag, but, after taking a moment to compose herself, and getting her breath back, she’d resume and get straight back into it.
I felt the familiar feelings, I was going to cum and I pressed my fingers gently into the back of her head.
“Helen, I’m going to come soon. You don’t have to take it if you want you can finish me by hand.” I whispered. Without lifting her head from my cock, she shook her head and mumbled something which I took as, “it’s okay”, and she continued to suck me.
When I came I came hard. It came from deep within, and I grabbed her head and thrust up and cried out as I felt my cock erupt in her mouth and the first hot, sticky jet of cum flew from the tip of my cock and splashed into her mouth. I heard her moan and felt her throat muscle clench as she swallowed and then, as my cock continued to spasm and twitch inside her mouth, she increased her suction and almost sucked my cum from me. It was intense, and every time she sucked and drew more cum from me I felt my whole body tingle and shiver, it was a fantastic orgasm.
When I had finished, I was drained and my head fell back onto the pillow as she slowly pulled her head from my cock, licking and cleaning me as she did. She finished with a final lick around the tip of my cock and then licked her lips and looked up at me. I grinned.
“Excuse the language Helen, but fuck! Where did you learn to do that?! I sighed.
She smiled and knelt up.
“It was okay?” She asked.
“Okay? You’ve got to be kidding me, it was fantastic!” I replied.
I sat myself up and she looked at me, she once again turned into the shy, timid woman that I had first met online, and she looked at me to lead. I smiled and ran my fingers over the sheer, black stockings and onto the soft, pale flesh of her thigh. I traced my finger slowly along the length of one of the black suspenders that held up her stockings.
“I have only one request, Helen,” I whispered.
She raised her eyebrows and I looked into her eyes.
“Leave these on.”
She nodded. And I took her in my arms and kissed her, as I did I reached behind her and unclipped her bra. She held her breath as I slid the straps down her arms and let the bra fall onto the bed. Then, I slowly lowered her down onto the bed and as I leaned over her she looked up at me. I brushed a few strands of hair from her eyes that had fallen then kissed her again.
She slid her hands around my back as we kissed and I stroked my fingers across the soft, full mounds and tweaked her nipple. I broke our kiss and lowered my lips onto her other nipple and sucked it gently. She moaned softly as I worked her nipple between my lips, nibbling it and tugging it gently as my fingers did the same to her other nipple.
I felt her fingers slide through my hair as she began to let herself go and she pulled my head tighter to her breasts as I sucked harder on her nipple, flicking my tongue across it as she moaned and panted beneath me.
With my lips clamped to her nipple, my hand slid down her body. I felt her stomach shiver as I caressed my fingers across her soft flesh and slipped them inside her creamy satin knickers.
She sighed as my fingers contacted her soft, downy hair that covered her pussy. She gasped when I slid my fingertip across her clit, she pushed her pussy up against my hand in response. I continued down, and let out a sigh when I felt my finger slide between her lips and her warm, moist pussy. She parted her thighs involuntarily as I slid my finger inside her and she groaned and tugged her fingers around clumps of my hair and cried out.
I worked my finger slowly in and out of her as she moaned and clawed at my head and I could feel her getting wetter and wetter.
I slid down her body, and she let out a sigh of disappointment that I had stopped working on her nipple, and had removed my finger from inside her. I knelt at her feet and reached up, I started to peel down her knickers, and as they slid down her thighs, I stared, as I revealed her pussy, which had a nice full covering of greying brunette hair.
I ran her knickers down her legs and dropped them onto the floor. Then, I pushed her legs apart and knelt between them, and lowered myself down until I was laid between her thighs. I could smell her pussy, and it smelled so good, and I could see beads of moisture clinging to the hairs of her pussy and around her swollen lips.
I inhaled again and stared closely at her clit, then I lowered my mouth and covered her pussy and pushed my tongue between her lips and inside her. She let out a long moan and lifted her knees, her feet crossed behind my back and she gripped my head between her thighs.
I worked my tongue along her lips and inside, she tasted so good, and she was soaked. Then, I turned my attention to her clit and sicked it between my lips before rolling it around and then nibbling on it. She let out a cry and tugged hard at my hair, her thighs gripped my head tighter as she pushed her pussy harder against my mouth.
She began to grind her pussy against my mouth as I worked my lips on and around her clit her moans and cries became louder and more frequent and she began to grind against me even harder. She was moving around and it was tricky to keep my lips clamped to her clit, but I managed it, and as I did I slid a finger inside her pussy which was now dripping wet.
She clawed her fingers at my head and pulled at my hair.
“Oh fuck James! What are you doing to me?” She cried.
I smiled, but couldn’t respond as I had my mouth full, and judging by her actions she didn’t want me to stop, so I kept licking, sucking and nibbling.
When she came, it was a violent experience and I felt it first inside her pussy, I felt the muscles contract around my finger tightly, then, she clamped her thighs around my neck so tightly that I apart from the pain, I found breathing difficult. When her orgasm hit her it seemed as if her whole body was responding, she shook and bucked beneath me, her hips thrust up and down and she almost pulled my hair from my head. She let out a scream as the full force of her orgasm hit, then, she threw her head back onto the pillow and panted and gasped for air as her body spasmed and twitched as her orgasm swept through her.
I stayed between her thighs while her orgasm swept through her and as it started to subside she relaxed the pressure on my head and I was able to move it. I lifted it and looked up at her, she was staring at the ceiling, her mouth wide open as she gasped and gulped in air as the final few spasms of her orgasm left her body. I knelt up and wiped my hand across my lips, they were soaked in her juices. I looked down and I could see her lips glistening with moisture.
I shuffled forward and slid my fingers around my now hard again cock. I brushed the tip between her lips and she looked down at me, I smiled at her.
“Ready?” I asked.
She nodded, her eyes wide, she was ready.
I supported myself on one arm as I guided the head of my cock between her lips and pressed it against her tight opening. She groaned and closed her eyes as I pushed and felt her resist. I knew that I was bigger than her late husband, I paused and pushed harder. She moaned and then let out a soft cry as the head forced it’s way inside and I groaned as I felt her tight tunnel grip my shaft as I slid it slowly into her.
“Hmmm, oh god Helen, you’re tight.” I moaned.
She gripped my arms with her hands as I pushed deeper into her until I had fully penetrated her. I held myself off her body as I lay over her, my cock deep inside her. She opened her eyes and smiled.
“Oh, that feels good” She whispered.
I started to move inside her and she lifted her feet and hooked them behind my thighs and as I lowered myself down onto her body, she wrapped her hands around my back and started to push back as I quickened my pace and fucked her harder.
We got into our rhythm and I was soon slamming into her as her fingers dug into the flesh on my back. Her pussy was tight and I could feel her muscles gripping my shaft as I pounded into her. The room was filled with our cries and moans and the occasional yelp from her and grunt from me as we worked ourselves almost to a frenzy.
I hooked my hands under her back and gripped her shoulders which allowed me to thrust harder into her. Her body rocked with each thrust, a cry from her lips as I slammed into her my only thought was for my orgasm. I felt her nails scratch down my back, the pain was pleasurable and only spurred me on to fuck her harder.
The end came suddenly. I felt my legs tingle and almost cramp as I slammed into her, then I threw my head back as I felt the first spurt of cum shoot into her and I cried out.
“Oh fuck! I’m coming!”
I thrust deep into her and held my cock inside her as it twitched and jerked with each emission as my cum forced it’s way out of my cock and splashed into her pussy. My head dropped and my face pressed into her neck as the final few drops of cum oozed from my cock and slipped inside her.
We lay together, panting and breathing in air as we both began to recover. I don’t know how long we lay there, but I felt her fingers stroke softly across my back and I lifted my head and looked into her eyes.
“That was,” I put my finger on her lips and stopped her.
“Fantastic,” I said and kissed her.
I rolled from her and lay beside her as we both slowly regained our composure, my fingers stroked along her arm as she lay her head on my shoulder.
I held her for a while as we both lay in silence and I listened to her breathing. I turned onto my side and looked into her eyes.
“That was special Helen. I hope that you agree.” I whispered.
She nodded. “I do. It was the best sex that I’ve ever had.” She replied.
I smiled and kissed her.
“Thank you. And, I hope it is not the last. I think you deserve to be happy Helen, and I’m sure that there is a someone out there who can make you happy.”
We lay together for a while longer. She told me that there was, in fact, someone that she was interested in, and he had already made it clear to her that he was interested in her. I asked her why then had she chosen to do this with me. She grinned.
“I wanted to see if I could do it. And, to be honest, I thought that you were sexy, and the thought that someone like you was interested in me was such a turn on.”
I smiled, and blushed, but thanked her.