Landlady & Friend

It was the summer of 2018, I was 21 and had just finished a gruelling 3 year University degree. I had passed with flying colours and obtained my degree in business studies. After 3 long years studying without a break, I decided to look for a short holiday, a week or two away to unwind.

I looked on the Internet and fancied somewhere on the South Coast of England. I filtered out some options and decided on Dorset.

One place really stood out, it was a 2 bedroomed house about 5 minutes from the coast. The room looked really nice, it had a double bed and satellite TV too with a nice en suite. I decided to book in so I called the number.

"Hello, Sandy Lodge, how can I help?"

"Oh hi, I'm interested in the room, probably looking to book for a week, what's the availability?"

"It's free for the next 3 weeks as it's out of season, it's very comfy. There is a king sized bed, TV and en suite. How many are coming, one or two?"

"Oh it's just for me, I've just finished Uni and fancy a break for a week or so"

"Oh, a nice young man, OK. Its usually £95 a night but if you want to book a full week then I can do it for £70 a night. What do you think?"

"OK, sounds great, I'll pay now and do the week"

"Lovely, let me just get my bank details and I'll email you a receipt"

I made the payment and received the email confirmation.

"That's lovely, it's all gone through. My names Helen by the way"

"Hi Helen, I'm Steve, what time is good to arrive?"

"Oh anytime, the room is ready so just come when you fancy

" Lovely, I'll set off around 9 so should be there for around 2pm"

"Great, I'll see you then, safe travels"

I could've gone away with some friends, they were going to Ibiza but nightclubs aren't really my thing. I had plenty of time to do all of that, I just fancied a quiet week away. I packed a bag, had a beer and went to bed, ready for the early start and long drive.

I slept well and was looking forward to a week away. Nothing heavy, just a few nice walks along some of the trails, perhaps check out the local scenery and pubs.

I finally arrived so I parked up, luckily the house had enough space for 3 cars, there was only one on the drive so I parked next to it. I grabbed my bag and knocked on the door.

"Hi, you must be Steve, please come in and I'll make you a tea, you must be parched"

"Hi, you must be Helen, I'd love a tea, thanks"

She showed me the room which was great and we made our way into the kitchen.

"So Steve, what's the purpose of the trip then?"

"I just fancied a break after Uni really, nothing heavy, just a bit of time for me. I'm going to have to look for work in the next few months so just want to see some sights before I start working"

"Oh I see, and do you have a girlfriend?"

"Haha, no, I've not really had time due to such a heavy study workload. I suppose there's plenty of time to find someone and settle down"

"Of course there is dear, don't rush into it. Take my word for it, I got married far too young and just ended up resenting my husband. We got divorced 10 years ago as I couldn't put up with his boring ways any more. He was a good man and worked hard but he took me for granted. He barely looked at me, he just worked and played golf. So yes, you have plenty of time, just enjoy yourself and do things for you"

I must admit, I did fancy her. She was around 55 to 60 and was in really good shape. She was around 5' 6" to my 6' 2".

Helen had explained that she was retired but used to work as a teacher at the local comprehensive school. Her look was extremely tailored and she clearly had an eye for detail. Her dress sense was very understated but very classy. She was wearing a short brown skirt, tights and a black roll neck jumper and a belt with a gold buckle. The look was finished off with a gold pendant which hung between her breasts and a pair of leather ankle boots which had a slight, 2 inch heel. She looked fantastic and I couldn't take my eyes off her although I was trying desperately not to make it look obvious.

"OK Steve, I have to go out shopping. I may pop into town after to look for some clothes. Any requests food wise?, I thought I'd make some pasta later"

"Ooh lovely, if it's not too much trouble then pasta will be fine"

"It's no trouble, please make yourself at home, whilst you are staying here, my house is your house"

Helen made her way out so I decided to look around the local area. I had a walk for a couple of hours and returned to the lodgings. Helens car wasn't there so I let myself in and went upstairs for a lie down. As I made my way up, I noticed her bedroom door was open, I knew I shouldn't but I couldn't resist having a look. She had a large bedroom which was immaculate, there was even space for a 2 seater settee which gave fabulous views of the scenery outside. There was a door in her bedroom which led to an en suite, I opened the door and looked in. In the corner was a wicker laundry basket, I don't know why but I took the lid off and looked inside. A pair of her worn, black, scrunched up lace panties greeted me. My heart started to beat a bit faster as I took them out. I turned them inside out and saw a lovely white residue on them. My cock started to grow as I put them to my nose and imagined I was sniffing her pussy. I unbuttoned my jeans, took out my cock and started to slowly stroke myself. Just at that moment, I heard the door shut as Helen returned.

"Hi Steve, you there?"

"Just in my room, I'll be down in a minute" I was frantic with panic as I quickly buttoned up. To my horror she was on the landing and saw me coming out of her room.

"What are you doing in there Steve?, that's my room"

"I know, I'm really sorry, I was just looking around your house, it's so nice and you have great taste" I said, hoping she'd believe my rushed excuse.

"Oh, that's fine, thank you for the compliment. Dinner will be ready in 30 minutes, I'll give you a shout when it's out"

"Thanks Helen, looking forward to it"

She went to the loo in her room and I went to my room to watch a bit of TV. My mind was racing and wondered what she thought, here I was, a stranger, looking around her private room.

"It's ready Steve"

"Coming" I responded.

"Be a love Steve and grab the wine and a couple of glasses, white OK?"

"perfect"

I poured the wine and we ate, exchanging small talk about my afternoon and her shopping trip. Everything seemed to have passed regarding being in her room when she asked,

"Earlier Steve, when you were in my room, did you go into my bathroom? I only ask as the lid on the basket was off and I never leave it off. It was on before I left as I put some dirty clothes in ready for a wash"

Shit, she clearly knew I was looking.

"Err, I had a look at your en suite but when I heard you come in I think I knocked it off in a panic"

What a lame excuse I thought to myself. What she said next really surprised me.

"Come on Steve, you were looking at my knickers weren't you?, admit it, I don't mind, in fact it turns me on"

I gulped and went red, my cock started to grow.

"No honest, I just knocked it over, I wouldn't do that, honestly"

"Steve, we're all adults, you're not the first single guy to stay here and I doubt you'll be the last. If you like, we could have some fun while you stay, you're a handsome guy and I have needs. No pressure, just have a think about it. I won't be offended and I'm sorry to put you in this position. It could be fun though."

What followed was an uneasy silence, I was shocked by her words but still really turned on. She was super attractive and I fancied her, I just needed some time to think about it. I had only known her for about 5 hours but being a man, I was hugely tempted.

I helped her clear up and went to my room. Her words and the way she spoke was super confident, probably down to her teaching years. I heard her come upstairs and she went into her room, she left the door open so I went in. She wasn't there so I looked in her bathroom, she was sitting on the toilet having a pee as I walked in. She looked up, smiled, sat back and opened her legs so I could see.

Her piss was cascading down as she directed the jet down.

"Like what you see Steve?" she asked as her tongue rested on the corner of her mouth.

"Yes" I said coyly.

"Kneel down and I'll show you more"

I knelt down in front of her and she shuffled forward. Her skirt and tights were around her ankles.

"Take off my boots, skirt and tights" she said seductively."

My cock was on fire as she spoke, she was clearly experienced and that nice Landlady persona she had turned into a raging horny nymph before my eyes.

" Good boy, now let me show you what I have"

Her legs were wide open after I removed her skirt and tights. She expertly held her cunt open with two fingers whilst her index finger on the other hand was slowly running up and down her slit. Her lips were really big and they stretched really wide. She opened up her hole and and stuck two fingers deep inside herself.

"See, I told you it would be fun didn't I?

You've clearly smelt my dirty panties, now I want you to smell the real thing, stick your nose in my cunt" she ordered.

I didn't need to be asked twice and I pushed my nose deep in her cunt as she held herself wide open for me. I guided my nose up the crease of her cunt and felt her huge, swollen clit.

"Yes, lick my clit, I need it badly, suck on it and don't stop until I tell you. I've been imagining you doing this all afternoon, don't stop you naughty boy"

Her encouragement and confidence was a massive turn on. She was writhing and bucking on the toilet seat as she let out a huge cry.

"Yes Steve, yes, I'm going to cum, don't stop, don't stop, don't stop!"

She squirted all over me, I had never experienced it before and I was shocked, but hugely turned on.

She rocked back on the seat and was breathing really heavily.

"I knew you'd be good at licking my pussy. Fancy making me squirt like that, now go into my room and take your clothes off."

I did as I was told and lay on the bed. My cock was the hardest it had ever been and was oozing pre cum.

"Right then, your turn now"

She sat on the bed and stroked my cock. She rubbed her index finger on my tip and tasted my dribbling pre cum.

"Someone is excited, let me help you with that"

She cupped and squeezed my balls with one hand and wanked me with the other. She could evidently suck a cock as she greedily slurped and sucked away. My cock is around 7" fully erect but she made light work of it as she devoured it and took the full length easily.

"Stevie, you're not going to cum tonight, I know you want to but you're not. I have a plan for you you naughty boy. You won't regret it, just promise you won't wank yourself tonight. I want you to explode tomorrow night. Just trust me, I know you're very horny at the minute but this is nothing. Just trust me, you trust me don't you?"

I was disappointed as I was on the verge but I reluctantly agreed.

"OK, I promise, I'm intrigued though, what do you have planned?"

"All in good time sweetie, all in good time"

It was the morning after, I was still in a bit of shock as I went downstairs for some breakfast.

"Morning Steve, how was the bed, did you sleep well?"

"Yeah, great, I slept like a log, really comfy thanks"

"Oh good, want some breakfast?"

"Err, just some toast thanks, if it's not too much trouble"

"No trouble at all, sit down and I'll make you a tea too"

She had so much confidence about her, it was as though nothing had happened. I must say though, even in the morning she looked great. She had an oversized shirt on with the sleeves rolled up and just a pair of knickers. She was barefoot and just oozed confidence.

"Any plans today Steve?" she enquired.

"Yes, I'm going to go into Bournemouth for a look around, perhaps go for walk somewhere, nothing really concrete"

"Ooh, lovely, I love Bournemouth"

"What about you?"

"Well, I'm going to hop in the bath and then I'm going to lunch with a friend of mine and then we might go shopping In fact, we might come back here but we haven't decided yet"

"OK, sounds fun"

"I was thinking of introducing you to my friend, will you be in later, about 7ish?"

"Yes, I'll probably be back for around 4 so will definitely be here at 7, I've no other plans"

"Great stuff, right, enjoy your breakfast, I'm going for a soak"

This was probably what she had in mind, I now knew that she had planned a night with her friend and myself. My mind began to wander, what did she look like, younger, older? I bet she looked the same as Helen, glamorous and stylish with a horny undercurrent. Who was I to complain though? if they wanted to play then I was more than ready, I was beginning to get really excited at the prospect of two hot milfs to play with and them to play with me.

Helen came downstairs looking glamorous as ever.

"Right young man, I'm off out now, make sure you have a nice time. I should be back about 5 and I'll probably have another bath before my friend comes so make sure there is enough hot water"

"Will do, have a great time, see you later"

She came up to me, put her arms around my neck and gave me a slow French kiss. Her tongue was darting in and out of my mouth. She finished off by sucking on my bottom lip. She looked at me and said,

"Hopefully there will be a lot more later, have fun"

With that, she turned around and walked out of the door. It left me feeling so horny and that was probably her intention, if so, it definitely worked. It was about midday now so I decided to go out for a walk, I was on cloud 9 and the anticipation I felt was incredible. My stomach had butterflies, not through nerves but pure excitement. I wandered for a couple of hours, visited the local pub, had 2 pints and made my way back. I ran myself a bath in readiness. I grabbed my razor and made sure I was completely clean shaven down there.

I jumped out of the bath and dried myself off. I heard the door go, "Hi Stevie, only me, gosh I'm shattered. Do me a favour love, run me a bath and bring me a large glass of wine up"

"How was your shopping trip?"

"Oh it was OK, I bought a couple of things for later. My friend will be here in about an hour. Do me a favour, open the door when you hear the doorbell, I'll be down soon after"

"Sure, no problem"

I took the wine up and went downstairs and waited. Time seemed to really drag, it's funny how the more excited you are, the slower time goes.

It was now 7 o clock, Helen was still upstairs getting ready when the doorbell chimed. I jumped up and saw the silhouette of a man through the frosted glass. I opened the door.

"Hello there, you must be Steve, really nice to meet you, I'm Brian"

We shook hands and I followed him into the front room. I was really surprised but not altogether shocked as Helen was full of surprises.

Brian was around 65 I gauged, he was as tall as me, around 6' 2" and was immaculately dressed. He had a full head of grey hair which was side parted and brushed back. He was wearing a nice crisply ironed white shirt which was neatly tucked into a formal pair of navy trousers. His attire was completed with a lovely pair of tan loafers. He was clearly a stylish guy and even at his age, probably still turned a few heads.

"Helen still getting ready Steve?

"Yes, she's been upstairs for an hour so"

"How long have you known Helen for then Brian?"

"Get me a glass of Wine and I'll tell you Steve"

I returned with 2 glasses and he told me how they met.

"I was the Head at the school where Helen worked, I've since retired but Helen immediately caught my eye when she began working there about 20 years ago. We began chatting and I took her out a few times. She is great fun and we quickly became close friends. We have a sort of mutual relationship, you know, friends with benefits if you like. I'm married and my wife knows about Helen, they've even gone out socially. She's not the jealous type though which is really lucky for me, I'm not jealous either and she too has male friends. So there you go, that's my story, not much to it really, just two friends who like a good time. As for tonight, Helen told me all about you and thought I would like to meet you for one of her special evenings, as she calls them"

I felt really at ease with him, he was friendly and asked me about University. He encouraged me to get into teaching as rewarding career. We continued our chat and he told me about Helen and himself, what they got up to and what to expect from the meeting.

"What kind of things turn you on then Steve?, Helen and myself are very open about sex, anything goes and anything can be tried. We are all friends but we do respect limits too. If you're not comfortable with anything then we won't push you. The things I've seen Helen do, well, you wouldn't believe it. She's like a porn star but better because she doesn't do it for money, just pure enjoyment."

"She's such a dirty, kinky thing you know Steve, she told me how wet you made her when she knew you were sniffing her soiled, used knickers. As she was telling me I just knew we had to all get together. Helen said she'd try to arrange it and was confident you'd agree. Sounds like we are all kindred spirits, you just don't know it yet though. Just trust us and you'll have a great time"

She clearly told him everything, I did feel a bit embarrassed but figured that I didn't know him and after a few days, I wouldn't see him again. I vowed to myself that I was just going to enjoy whatever happened.

As we were talking, I could hear Helen coming downstairs, she went straight into the kitchen from the hallway before coming in to us. I heard the pop from a bottle and she entered the room. I couldn't believe my eyes, she was naked except for a pair of black leather high heeled T bar sandals. Her make up was amazing, thick heavy green eye shadow and deep red lipstick. Her hair was perfectly styled, it was in a parting to one side with the other side tucked behind her ear. She looked every inch the perfect porn star. She popped the bottle of champagne on the side table and said,

"How do I look boys?"

"Fantastic as always Helen" replied Brian.

"Absolutely stunning" I said.

My cock was so hard, I knew this was going to happen but this was now reality and I was fully in their hands.

Helen stood in front of, us turned around and bent over, playing with a buckle on her shoe. She gave us a perfect view of her fabulous shapely arse.

"Do you like my shoes boys?, they're new and I thought I'd try them out for my men"

"So sexy Helen, great choice" said Brian.

"But then you do have fabulous taste you little cock tease" said Brian confidently.

Her hands moved slowly up the back of her legs, she stopped at her backside to give us a glorious view of her arse hole as she spread her cheeks wide open.

She sat in the middle of us on the large settee, my heart was racing.

"OK boys, you've seen what I've got, now your turn. Take of those clothes for me"

We both stood up and removed everything. My 7" cock felt the biggest it had ever been. I looked over to Brian and my eyes nearly popped out. He had literally the biggest cock I have ever seen, I'm not joking, it was all of 10" long and I immediately felt a bit intimidated, but strangely enough, it turned me on even more. Helen had seen it all before though though, her tongue was seductively flicking from left to right on her top lip. She was in her element.

"Big isn't it Stevie, why don't you touch it? Brian won't mind, he loves to play with men as well as women, don't you Brian?"

I had obviously never touched another man's cock before and Brian sensed my ever so slight unease.

"H, leave him alone, he might not want to" he said sympathetically.

"Stevie, I promise you that you are in the right environment to try anything. Any sexual desires or fantasies can be lived out and explored with us. We are completely non judgemental and nothing goes any further than these four walls, what do you think? I tell you what, let me start him off for you. Watch me suck him, I want your cock in your hand whilst you watch"