Training Course

Often, when I was an apprentice, the company I worked for would send you on training courses. If there was not any residential accommodation at the training centre, you would be given a list of approved Bed and Breakfast hotels, and you’d be free to choose one to stay at, and claim back the cost of bed and board for the duration of the course. These establishments were most often run by middle aged ladies, and they would quite often take pity on the younger men and offer them an evening meal for an extra fee. I got the impression that they enjoyed the company, even though it meant extra cooking for them. I found the experience quite liberating, spending time away from my family, with my own room to come back to and no inquisitive family members wondering what I was up to alone in my room. It was wonderful to be able to leave the training establishment, walk back to the place I was staying at, and stop off at a news agents shop to purchase some adult magazines with which to entertain myself in the evenings.   One place I stopped at for two weeks was run by a widowed landlady, Mary. She was in her late 40’s, and as well as being friendly, a good cook, and having a happy, jovial demeanour, she had a lovely sense of humour combined with a very dirty laugh.  I could imagine her and her late husband having a great time together.   The first week of the course went by quite quickly, my routine of getting up, having a shower, dressing for breakfast, going to the training establishment, finishing in the evening, stopping off at a news agents’ for an adult magazine or three on the way back to the boarding house, then having a lovely even meal with Mary before retiring to my room for a long, lazy, languid masturbation session was perfect. Or so I thought until a chance incident at the beginning of the second week. Arriving late evening on the Sunday, ready to start the course good and early on the Monday morning, Mary let me in and said she’d make me some hot chocolate while I unpacked. Not wanting to be without any stimulation for a night time masturbation session, I’d packed some of the adult magazines I’d purchased the week before in my carry case. I was in the middle of hanging my shirts in the wardrobe, when there was a gentle tap on the bedroom door.   “Come in” I said.   The door opened and Mary entered with a mug in each hand.   “Thought I’d join you, if you don’t mind Richie?” she said. “I’ve no other guests for the week, so it’ll be just you and me” Mary continued.   “No, I don’t mind Mary” I said, hoping that she’d not stay too long so that I could get to bed and pleasure myself.       As she sat there on my bed, and I continued unpacking, we chatted about our lives, what I’d done over the weekend, her children who had grown up and flown the nest.   “Richie, do you have a young lady?” she asked me.   Blushing, I admitted that I did not have a girlfriend.   “Oh, don’t worry, one will come along” Mary said, smiling, “and when she does, you’ll not need to use those top shelf magazines” she added, winking at me, “or at least you could share them with her”.   “What magazines do you mean?” I asked, playing the innocent.   Mary chuckled. “The ones you have been buying from the news agent down the road” she said, looking at me.   “How on earth did you know that?” I asked, embarrassed.   “Richie, it’s a small town. The lady that runs the news agent is a gossip. She described you to a tee” Mary explained.   “Oh” was all I could say.   Mary chuckled throatily. “Hey, don’t worry. It’s not as if I was your mother about to tell you off. In fact, my two sons used to buy similar reading material, although I doubt they read much in the magazines, just enjoyed the pictures. I’m sure you know what I mean, don’t you?” she added, raising her eyebrows.   Blushing, I asked, “It didn’t bother you that your sons had similar magazines?”   “Bother me?” Mary said. “Oh, you mean them getting off to pictures of semi naked women posing in the magazines? No, it didn’t. Every young lad does it, masturbate that is” she said, “even women enjoy a little fiddle now and again”, Mary said looking at me with a smile playing on her lips.   “Including you Mary?” I asked, daringly.   Mary burst out laughing. “Me Richie? Of course, yes, I enjoy a good masturbation session, it relaxes me. Have I shocked you, a woman of my age admitting that they enjoy a wank?” she asked me.   “Well, yes, a bit” I admitted blushing.   Mary chuckled. “There’s no need to be shocked. I’m not embarrassed to admit I love to play with myself, and neither should you be Richie. Better to release that pent up tension than get frustrated, I say” she said, grinning at me. “In fact, I think I’ll head off for a little playtime right now, Richie. This chat about masturbating has got me in the mood.”  As Mary stood up, she looked at my crotch and nodded at the bulge there. “Seems you need to crank one out too Richie, by the look of that bulge” she added with a dirty little laugh.     I just nodded, blushing.   Mary chuckled again, then picked up the two empty mugs and left the room. I listened to her footsteps as she walked along the landing, then down the stairs. I stood there for a while, my mind a whirl as I took in what Mary had revealed. Then I finished unpacking and finally undressed and lay down naked on the bed, with my selection of adult magazines. As I flicked through them, I couldn’t help but wonder just what was going on down stairs. I imagined Mary laying on her bed, legs spread wide, caressing herself, her breasts, thighs and, of course, her pussy until she achieved orgasm. I couldn’t help but wonder whether she was shaved down below, or had hair. I flicked to the pages of the magazines that contained photos of the wives, girlfriends and lovers of the male readers, rather than the professional models. Often these women were older, more mature, and I wondered if there were any who looked like Mary. Sadly, there weren’t. I was by now, extremely agitated, with a rock hard penis that needed attention.. Sod it I thought. I got up, pulled on a t-shirt and my pajama bottoms, and carefully, quietly left my room and slowly walked along the corridor then down stairs, my hard on quivering as it poked out of my pj bottoms. As I got to the bottom of the stairs, I saw that Mary’s bedroom door was wide open, but the lights were off. I took a quick peak inside and was disappointed to see her room empty. Then, as I was about to head back upstairs, I saw flickering light coming from the lounge. The door was ajar, and curious, I tip toed to it and looked inside. What I saw caused me to catch my breath. The television was on, but the screen was displaying the feed from the video recorder. The images on screen were of naked men and women, writhing in complete abandon, some having sex with one another, threesomes, moresomes, some just watching and masturbating, or being masturbated by someone they were sat or stood by. Basically, it was a video of an orgy. I couldn’t help but stare as I’d never seen the like before, and of course my hard cock started to throb as I got excited, and I could feel pre-cum oozing from the tip of it. I gripped my stiff cock as it poked out of my PJ flies and began slowly masturbating.   “Are you just going to stand there and stare while you wank off Richie, or are you going to come and join me on the couch?” asked Mary with a throaty, husky voice.    I jumped with shock at hearing her voice.   Mary just chuckled, and said “Come on, come and sit here with me. Don’t be shy. Let’s watch together, and if you want to carry on playing with yourself, then please, feel free to do so. I’ll happily confess to you that I have been masturbating as I’ve watched this video, so I won’t mind you pleasuring yourself if you wish to too. In fact, I’d rather enjoy your company”.   Although shocked, I was excited at Mary’s suggestion. Masturbating while a woman watched me was a long held fantasy of mine. I walked over to the couch, my hard cock wobbling as it poked out of my PJ’s.   “Nice cock” Mary commented as she watched me, a smile playing on her lips. She patted the seat next to her and said, “sit here Richie”.   As I sat down, I couldn’t help but notice that Mary’s dressing gown was only loosely closed, and that a pair of her knickers were on the floor at her feet.      “Never seen a porno video before Richie?” Mary asked me, her eyes on my hard cock.   “No” I muttered, transfixed by what I saw on the screen.   “Well, do you like it so far?” Mary asked me.   “Yes” I managed to mumble, my hand moving to my cock.   Mary watched as I began to masturbate, and chuckled. “Good lad. I told you it was ok to relax and enjoy yourself while staying here. In fact, I suspect that we’ll both have a good time while you’re here this week”. “Feels good, doesn’t it Richie, wanking while sitting by me?” Mary asked after a little while.   I nodded as I continued to watch the action on the screen while stroking my cock. Then I glanced over at Mary and found her watching me closely as I masturbated, rather than watching the on screen porn.   “I hope you don’t mind me looking Richie? It’s nice to see a hard dick in the flesh for a change, rather than watch a porn video” Mary said.   “Mind? No, of course not Mary” I replied, smiling.   “Good lad. Anything on the video got you particularly hot and bothered Richie? If there is, I can always use the remote to replay it for you” offered Mary, as she carried on watching me wanking.   “Well, there was one bit” I confessed.   “Oh?” she queried.   “Yes, a little while back, a woman was on her hands and knees ………..” I began.   “Ah, the older woman who gets fucked doggie style?” Mary asked, chuckling.   “Yes, her” I managed to say, finding it wonderful that this older woman sitting beside me was so openly talking dirty.   “I loved that part myself” Mary said, “especially when the young man fucking her so hard pulled out and shot his load over her rear and back. Very arousing scene” added Mary as she rewound the tape to that scene.   “Yes, very arousing” I agreed, my breathing getting louder with my excitement at being able to view it again.   “I can tell Richie. You certainly seem to be finding it very exciting judging by how you are breathing” whispered Mary, huskily.    I turned my head to look at her again, and found that she had opened her dressing gown, and was massaging her breasts using her free hand. She pinched and pulled at her nipples as I watched, causing them to swell and stick out, erect. Mary noticed me watching, winked at me and said, “Seen real tits before Richie?”   I just shook my head.   Mary chuckled. “Didn’t think so. They are real, no plastic involved. Want to feel them?” she asked me.   I nodded, and she took my free hand and placed it on her left breast.   “Go on, have a feel, don’t be frightened, fondle them, squeeze them, play with them” she ordered me.   So I did. I caressed, fondled, squeezed, kneaded them, then rubbed her nipples with my thumb, all whilst slowly stroking my cock. Mary sighed with pleasure whilst I played with her breasts. She paused the video and dropped the remote control on the floor, leaving both her hands free. She moved one hand down between her thighs, and the other she placed over my hand, the one I was stroking my cock with.   “May I Richie? I want to feel your dick in my hand. Please” Mary almost pleaded, as she used her other hand to play with herself.   I let go of my cock and had my hand replaced by Mary’s. Her grip was firm, although her skin felt soft. Mary gently squeezed my hard cock, before slowly stroking it. I sat back on the sofa and sighed contentedly.   “You like?” Mary asked me.   “Yes, a lot” I managed to say.   “That’s good” Mary said in her husky voice, before she proceeded to stroke me faster.   “Oh shit” I muttered.   “Want me to stop Richie?” Mary asked me, chuckling.   “No, it’s just that I’m not sure how long I’ll be able to last Mary” I replied, panting.   “Silly boy. Why do you think I’ve been encouraging you to wank off? I’ve wanted you to wank that cock of yours in the hope that I’d get to watch you doing it, and maybe even be allowed by you to have me wank you off too. I’m a horny old lady Richie, and I want you to spunk for me. You do want to cum for old Mary, don’t you lad?” she asked me in her husky tone of voice.         “Fuck, yes” I muttered.   “Then do it lad. Don’t be frightened. There’s no shame to be felt in letting yourself go with me here beside you. I really want to see your spunk fly” she urged me as she stroked my cock faster and gripped it harder.   My breathing got faster, I began panting.   “That’s it my Richie, come on now, don’t hold back now, let old Mary see what you can do” Mary urged me, adding “Imagine it’s me on all fours in that video, and that it’s you fucking me from behind, doggie style. Would you like to do that Richie, fuck me from behind, then pull out and spray your spunk over me?”  Mary asked me.   My answer was to spunk as she stroked my hard cock. My spunk erupted from my cock, flying across the room and splattering on the TV.   “Fuck me!” Mary gasped as she continued to pull on my cock, getting more spunk out of me.   “Shit Richie, that’s a lot of spunk you’ve got there” giggled Mary.   “Sorry” I gasped.   “Crikey me lad, don’t be. I love seeing lots of spunk flying, especially when I’ve had a hand in causing it, if you see what I mean” chuckled Mary, still holding my pulsing cock, my spunk now spurting onto the floor in front of us.   “Really?” I managed to ask between panting breaths.   “To be honest with you Richie, I’ve always loved tossing off men ever since I first did it at 14. It’s always made me horny. My hubby loved me doing it to him, and I have to confess, I really love tossing off young lads” she admitted, blushing.   “Oh?” I said.   “Yep. They are so eager to be handled and tossed off by a mature woman. I love their keenness, and the fact that they not only cum heavily, but that they recover quickly and can frequently spunk again and again, with the right encouragement of course” said a smiling Mary. “Can you keep a secret Richie?” Mary asked me.   I nodded.   “Well then, I’ve a confession” said Mary as she began tugging my now flaccid cock. “I’ve actually tossed off my son’s friends when they’ve stayed over. Does that shock you Richie?” Mary asked me.   “A bit I suppose” I said, “but then again, I don’t suppose that they’d have minded getting hand relief from such an attractive woman” I added, feeling my cock to begin to get hard again in Mary’s hand.   Mary giggled. “No, they didn’t. You think I’m attractive then Richie?” asked Mary as she continued to pull on my swelling cock.   “Very” I admitted.   “That’s kind of you lad. Hmm. Well, your cock seems to be agreeing with you” said Mary as she gently squeezed my now hard again cock. “Do you think you are up to spunking again Richie?” asked Mary.   “I’d like to try Mary” I said, now fully aroused again.   “Fabulous” Mary commented. “Do you want to toss yourself off while I watch, or would you like me to help you along again?” she asked me, gripping my cock tightly.   “Help me. Please” I almost begged.   Mary let out a throaty chuckle.   “Good answer” she purred as she once again firmly gripped my stiff again cock and began to masturbate me.   “That feels so good” I whispered as Mary increased her hand speed.   I looked at Mary as she masturbated me. Her eyes were sparkling, her face flushed. She licked her lips and her breathing was became faster as she sped up her wanking of me.   “Enjoying yourself?” I asked her.   Mary looked me in the eyes and said, in a husky voice, “Too fucking right Richie. Now come on, spunk for me lad, spunk for a poor, lonely, old, horny lady. I want you to show me you can shoot off again”.   “Keep going like that and I will!” I said.   “Do it then!” ordered Mary in a firm, commanding tone. “Come on Richie, cum for Mary” she demanded, as she frantically masturbated me.   “Oh God” I muttered as I could feel myself about to spunk.   Before I could take in her actions, Mary lent over and put her face in front of my cock just as I spunked for the second time in minutes.   “Fuck” I said, as my spunk splashed all over Marys freckled face and hair.   Mary just sighed contentedly as my spunk splashed onto her face, then ran down her neck and onto her breasts.   “That Richie was just what Mary needed” she said with a sigh.   I just sat there, stunned that a woman older than my mother would have not only masturbated me to a climax, twice in minutes, but let me cum over her lovely face.   “Lost for words Richie?” giggled a spunk covered Mary.   “Yes” I managed to croak out.   Laughing loudly, Mary said, “Well, actions speak louder than words, wouldn’t you agree?”   I just nodded.   Mary chuckled. “Right lad. I think that’s enough for tonight. You need to get to bed if you’re to be up bright and early for that course of yours tomorrow”.   I nodded again, and stood up, my cum covered cock hanging limp out of my PJ bottoms. I looked at Mary, her face sticky with my spunk, globules still trickling down her neck to her fulsome breasts.   Noticing me looking, Mary asked, “Perhaps tomorrow you’d like to wank off and spunk over my breasts Richie?”   “Would you let me?” I asked in turn.   “Richie, you can wank off and cum on any part of my body you want to” Mary replied. “Deal?” she asked me.   “Deal” I agreed. Then I headed off to my room, tired, yet excited at what would happen for the rest of my time lodging with Mary.