A gay sex stories: Into the Woods Ch. 03 I rushed home intrigued as to what the box contained, in the safety of my bedroom I pulled the ribbon loose
I took out a pink tissue package unwrapped it and found a pair of red lacy knickers, he wants me to wear these? I held them up and studied the shape of them, the fabric was silky and to my surprise I started to get aroused, undressing I stepped into the panties, pulling them up over my semi erect cock I turned and admired my firm young arse encased in the delicate red lace fabric, the front was sheer showing my full now erect cock running at an angle up my thigh.
I stroked and pulled the panties tight into my butt cheeks, I felt hot, I felt wanted, I felt so fucking horny, I wanted him now naked in my bed so he could see, I wanted his hot seed soiling them.
I pulled my now steel hard cock from the side of the knickers watching myself in the bathroom mirror, taking my shaft in my hand I began a slow wank imagining Tony was with me his hands caressing my plump arse cheeks, my cock spewed its second load that day.
Picking up the box an envelope dropped to the floor. Collecting it up I opened it and read,
“D,
I have to go away for a few weeks but I won’t forget you and I hope to meet up on my return.
I hope you don’t mind the small gift, it’s a fetish of mine and I hope you’re not offended.
T x”
Oh well I thought it’s only a few weeks, I’ll have to find some new playmates while he is away.
That night I slept wearing the red lacy knickers, my cock throbbing inside the sheer fabric. I had to decide wether I wanted Tony to fuck me, dreaming of his cock I drifted off to sleep.
The rest of the week was frankly weird, for some reason every day that I dressed I chose the red panties to wear instead of my normal underwear, it felt wrong but exciting.
Riding the bus I wondered what people would think if they knew, the fabric felt lovely on my skin especially when the lace back rode up my crack. It felt very naughty and very sexy.
That weekend I was alone in the house and of course horny, I lay on my bed wearing the knickers lazily stroking my cock, my other hand drifted lower between my cheeks and I used a finger to rub my sensitive hole, a bolt of electricity shot through me as I buried my middle finger up to the knuckle.
I ran to the bathroom and rummaging about found a jar of Vaseline. Returning to my bed I unscrewed the jar and put a glob of the gel on my finger and began to tease my ring. In went the finger again and I began to moan with pleasure, getting some more gloop from the jar I tried two fingers, it was painful at first but after a while my warm channel accepted the intrusion and it became pleasant.
My mind now was in overdrive, rushing downstairs I started to look for something bigger, something shaped like Tony’s magnificent cock.
I searched frantically aware that I had limited time, picking up a screwdriver I studied the handle, mmm maybe. Standing in the kitchen just in my knickers suddenly I had it, pulling open the fridge door I selected a curved courgette (zucchini for my oversea readers).
Rushing back upstairs I positioned a mirror by my bed and lay on my side, one hand pulled my cheeks open while the other pushed the cold vegetable against my hole. It felt very big but I persevered determined to get the damn thing inside me.
After ten minutes or so and some more lubricant suddenly an inch slipped in, and it hurt like hell. How can this be pleasant I thought to myself, I let it rest there for a while getting used to the intrusion, I pushed again and it broached my muscle and disappeared into my boy pussy, I cried out in pain biting the duvet in distress. I lay there for a while and a warmth started to radiate in my bowel, tentatively I began to work it in and out and the tip rubbed against something inside, I didn’t know what it was and I didn’t care, the feeling was incredible and my cock began to seep copious amounts of fluid in response.
Shit if my family and friends could see me now fucking myself wearing ladies knickers, I had become a slut for this man. Increasing the pace my cock erupted without any contact from me and I lay there totally spent.
After a few minutes I removed my new toy realising that if this was going to happen I needed to learn how to clean myself properly, I hobbled to the shower in some discomfort but happy with what I had achieved.
Monday came around quickly and I got ready to go to my job in town working in a menswear shop, it was boring but it paid well. The owner was a kind older guy and I started to suspect his motives for hiring me. I caught him watching me furtively on several occasions and wondered if I should flirt with him for fun.
That evening while we were locking up he informed me that he was going to retire but my job was safe, the new owner had agreed to keep me on and in addition I was to receive a pay rise. I thanked him and held out my hand, he took it softly, as we shook I looked him in the eye. “You have been very kind to me Mr Cooke, I wish I had a way of repaying you”, he was blushing which was very cute. “No, no not at all” he stammered, “you’re a good lad and its been a pleasure having you….er I mean being with you..uuum no working with you”.
I smiled at him and he looked flustered as he realised we were still holding hands. I actually felt sorry for the guy, knowing his buttoned up church going wife I reckoned he never had anyone go down on him, ever.
“Anyway must be…..umm.. must get going I suppose”, his voice was a bit croaky and his eyes glazed. I sensed sadness and suppressed desire behind them.
Placing a finger on his lips to shush him and still holding hands led him to the back of the shop to the changing booths. Looking at him with the best innocent face I could muster I said in a husky voice “Mr Cooke, can I ask your advice?”. “Yes of course” he shakily replied. “Well…uum…my mum has always bought my underwear which is a bit boring if you get my drift so I decided to get my own but I think I accidentally bought a…..uum…..ladies pair”.
He audibly gulped. “Ah, easily done I suppose if your not used to buying your own, perhaps you could…..um…..show me and I’ll be able to tell you” his voice was strained and his face scarlet.
“Oh Mr Cooke that would be soooo helpful” I replied surprised at the girly pitch in my voice. I grabbed his tie and pulled him into the nearest cubicle, looking at him I removed my shirt then swiftly pulled off my trousers, his eyes nearly shot from his sockets as he looked at my panty clad semi erection neatly packaged beneath my sheer knickers.
He was shaking as I drew the curtain, there was no need as the shop was locked up, but I thought he may feel more relaxed, I took one of his hands and let him caress my young smooth body, his hand went lower and brushed my erection, soon both of his hands were all over me gently caressing my body, I placed his hand inside my panties and let him touch my hard cock, his breath was coming in short gasps.
“Is this ok?” I whispered, he nodded.
“And this?” as I unbuttoned his shirt and caressed his hairy body, he nodded again.
Noticing the tent in his trousers I placed my hand on his crotch and sweetly whispered “can I help you with that?” He nodded dumbly as I sat on the bench and reaching around him pulled his body closer. Not breaking eye contact I slowly unbuckled his belt and let his trousers drop to the floor. “Ok?” I asked, he just nodded. I touched the outline of his rapidly inflating cock and he shuddered. I traced his length to its flared tip and dabbed my tongue on a wet patch that was growing. I kissed the patch tasting him then began to kiss his now fully engorged cock through his briefs before slowly and seductively pulling them down revealing his black pubic bush.
Nuzzling into them I revealed a little more until his cock sprang out, not huge but a nice five inch specimen with a very suckable swollen head. My lips made contact and I started with small kisses on his helmet then kissing and licking the underside of his shaft tracing a pronounced vein to the base, burying my nose into his groin I cupped his balls then ran my ringer under and towards his warm hole.
The noises he was making convinced me no one had ever pleasured him like this before and boy was I going to make it something he would always remember.
I felt his body convulse as I probed his anus and sensed he wasn’t going to last long so I engulfed him in my wet mouth taking as much as I could manage, he placed his hands on my head as I sucked on his solid shaft running my tongue around his cock head, my slurping sounds increased as his hips buckled and flooded my mouth with his semen.
Cleaning him up the best I could I pulled up his underwear, then his trousers and kissed him on the lips. “Thank you” he said hoarsely I dressed quickly, kissed him again and let myself out.
Smiling to myself I sauntered home, a strong cool breeze whipped down the Main Street so I dug my hands into my pockets for warmth. Feeling a small crumpled card I pulled it out and read with interest.
Henry Walters Solicitor, and the address of his chamber’s location in the town.
A wicked grin appeared on my face as I formulated a plan.
On Wednesday my new boss told me I was to be the sole employee in the store as he had commitments in another a few miles away in the next town.
” So you will be the sole key holder responsible for unlocking the shop and closing each night, is that ok?”, Too fucking right I thought, it couldn’t be better.
That night I wrote a note to Henry Walters Esq signing off as Bob which made me laugh as it stood for “boy on the bus”. A small detour in the morning led me to his offices and I popped the letter in the polished brass box, turned and set off whistling to work.
It was a dull day without much trade which as just as well as I had invited Henry to the shop at five concerning some “urgent matters” that needed addressing and my mind was frankly elsewhere.
My heart was beating faster at four thirty and hammering in my chest as it neared the hour.
Would he come? I wondered and if so what would he expect.
The door swung open and there he was, my heart skipped a beat as that day on the bus I didn’t take too much notice of him, just his hard throbbing cock in his hand, he was a very handsome guy, I guessed early sixties and in great shape.
He smiled showing his perfect teeth. ” Hello Bob, I wondered if I would ever see you again”.
I walked behind him, dropped the shutters and locked up, then turned to face him. Smiling I approached took his hands in mine and kissed his mouth.
He took a step back. “Wow, what happened to the shy boy on the bus?”, “He grew up” I replied.
I took his hand and let him to the rear of the store. “So Mr Walters what do you like to do in your spare time?” I asked coyly. “When I can get away from the family beautiful boys like you” he replied.
Needing no further answers I undressed slowly in front of him, tossing my shirt aside I kicked off my shoes then lowered my trousers, they were in turn kicked and I stood in front of him semi hard in my briefs. “Your turn” I whispered.
I had never seen a man undress so quickly, not that I had seen many, and in Ninja speed he had fully undressed, his expensive tailored clothes unceremoniously dumped in a heap. His cock was standing fully erect, I reckoned six inches quite slender and perfect for my needs, his body was a beautiful sight dusted with salt and pepper hair with well defined muscles for a man of his age.
Taking off my briefs my hard cock sprang up and I asked him hoarsely “Will I do?”, covering the ground between us at warp speed our bodies and cocks pressed together, he was moaning and in between kisses telling me what a beautiful boy I was and how hot and young I made him feel. I pulled away from his mouth and began my descent stopping via his nipples as I lapped and sucked on each one in turn, he moaned and threw his head back as I grasped his cock following the trail hat led me to his hot solid member.
His cock head was now at my wet wanting mouth and on my knees looked up and a began my oral assault. He tasted wonderful a mixture of man musk and cologne, my hands gripped his buttocks and he began to slowly face fuck me, by the sounds he was making I reckoned I was getting quite good at this.
Kissing the length of his shaft I cupped his ample balls and gently felt their weight. “Be careful, they haven’t had a decent release for a while and I want my seed elsewhere” he said in between moans and pants.
He lay down and beckoned me to him, pressing my body on his we went for another round of kissing until he instructed me to reverse my position so by head was between his muscular thighs again. I soon realised in this position my stiff cock was on his face and he wasted no time in engulfing my head and shaft into his warm mouth, fuck the man could deep throat and it was driving me wild.
I began to worship his cock again as he repaid the favour, I lost track of time as we both enjoying each other’s bodies. He stopped and pushed my body down slightly and I felt the warm sensation of his tongue lapping at my boy pussy.
I rolled off him thinking it’s now or never and reaching into my trouser pocket removed my tube of lube. I straddled him once more and handed it to him. “For you or me?” he asked. “It’s for me but go slow you’ll be taking my virginity”.
“Oh you beautifulu boy it will be me privilege and pleasure”.
As we kissed I felt the cool lube on my rosebud as he slowly worked his fingers inside then liberally smeared his cock head.
“You ready?” As much as I’ll ever be I thought.
I lowered myself onto him and felt his cock head probe at my entrance, then slowly took his mushroom head into my warm channel. It stung like crazy but my previous home study had served me well and soon I had his head past my muscle and after a while had the whole length inside me. I sat and marvelled at the sensations his cock was creating inside me as I gently rose and fell back onto his hard cock.
He twisted my body around and we both lay on our sides as he tenderly fucked me from behind, his arms were around me as he kissed my neck and cheek, I was in heaven as my orgasm began to build, he sensed it and began to piston faster into my willing hole. His thrusts became more urgent and as he grabbed my cock his creamy load entered me as I simultaneously shot over the floor, it was incredible.
We lay there for a while regaining composure, chatting and kissing until it was time to go.
He asked if I would like to see him again “Definitely” was the reply.
Five o’clock and I walked towards the door ready to lock up but it swung open. Shit, just what I need, I walked to the front of the store and began my sales patter, “Hi I’m Dave if you need….any…..help” my voice dried up, it was Tony.
I could have run up to him and thrown my arms around him but felt shy.
“Yes I think I need some help, I need some new underwear please, especially today its so warm and I’m a bit sweaty downstairs if you get my drift”.
“Uum yes” I stammered “I think I could find you something suitable.”
I turned the key in the door and shut the security blind.
He played with the fabric of a pair of briefs saying these were nice.
“Can I try them on” he said smiling.
I ushered him to the changing room and said yes but you have to buy them.
As the shop was shut there was no need to pull the curtain. He looked me in the eye as he unbuttoned his suit pants and dropped them to the floor. He reached out and took the pants from me.
“Can you help me try them on young man, I’m not as young as you and I may lose my balance”. He was obviously enjoying our little role playing so I decided to go with it.
“Yes of course sir”. I knelt before him and unlaced his shoes, taking each one off I pulled the trousers off, folded them neatly and returned to my “client”.
He had obviously just left work and his man scent was even stronger than before, his stiffening shaft lay to one side his flared cock head clearly visible inside his tight briefs.
I wanted to reach out and stroke him, to kiss his warm musky length but I resisted.
Still kneeling I pulled his briefs down and helped him out of them. His glorious cock sprang up fully erect and was again inches from my mouth.
Looking him in the eye I brought his still warm briefs to my nose and sniffed the gusset, his sweet man musk odour was slightly piss sweat sweet, I wanted to bottle it for my personal arousal.
I took the new briefs and placed each of his feet inside and began to pull them up his body, his now rock hard cock was refusing to fit inside.
“I think I need a little help there son”. I took his large warm erect cock in my hand and tucked it inside the fabric.
He turned around and I admired his firm muscular arse, I wanted to run my hands over him and fuck him hard in the changing room.
“Hmmmm..I’m really not sure if they suit me, what type of underwear to you wear young man”. I unbuttoned my trousers and slowly slid them down, his eyes grew wide as the red lacy fabric came into view, kicking off my trousers I stood before him my erect cock clearly visible in the sheer panties.
He approached me and a saw pure lust in his eyes, he nibbled my ear and whispered “you can keep my briefs and I’ll see you later, don’t you dare play with yourself”.
Then he dressed and was gone via the rear fire exit.
I sat slumped on the floor, picking up his used briefs I brought them to my face again.
My hardon was killing me. I gathered my things and went home.
Wednesday evening seemed to be the bedroom pacing day, should I go? I knew what he wanted but I wasn’t sure, his cock was big, very big and I doubted it would fit inside me, I had to admit up to now it had been the best sex of my short life so far, but this next step seemed a huge one, I was basically scared shitless.
And to my shame I had fallen for Tony and this ripped me to bits. In my head my life was mapped out, married, possibly a couple of kids, mow the grass on Sunday but he had blown this scenario clean out of the water.
I had started to find bigger “toys” and pushing them inside me slowly brought waves of pleasure sometimes ending with a prostate orgasm, which were intense and very different to my normal wank routine.
I undressed and lay on my bed, reaching under the mattress I pulled out his soiled briefs and inhaled the man scent, “fuck it ” I thought I’m going.
I cleaned myself and dressed, pulling back the curtains I saw that dusk had fallen, time to go to the woods.
Walking down the familiar track my legs felt like jelly, nearing my secret spot my heart was hammering in my chest. With a deep breath I ducked and entered.
Tony was there leaning against the tree, he quickly approached and put his arms around me. “You Ok?” he asked. “Think so” I replied hoarsely.
He sat and patted the space next to him, with shaking legs I sat.
Tony’s attitude seemed different tonight, he was very attentive asking me about my day, he laughed recounting his visit to the shop, we were almost like a couple sitting and chatting in the woods, he held my hand as we talked which felt comforting.
He kissed me.
“You sure you’re ok?”
I nodded and with a deep breath took off my tee shirt, pulled off my shoes and wriggled out of my jeans. I stood before him naked apart from my red lace knickers.
I sat back down next to him, I took his hand and placed it on my groin, he touched me lightly as he stared at my boyish frame dressed for him. I kissed his neck and began to unbutton his shirt. Running my hands over his chest I grazed his nipples, pulling the shirt from his shorts my hands roamed over his body kissing patches of his flesh. I suckled on one of his nipples as my hand went lower to unfasten his shorts.
Tony sat back and sighed, he stood and undressed before me. Stepping out of his briefs we stood looking at each other, this was so different than before, it was calm and sensual. Our cocks were excited but not yet erect, I went to him and wrapped my arms around his waist. I was aroused but afraid.
I began to play with his cock, holding it and rubbing the head until he was at full mast, dropping to my knees I kissed and caressed the object of my desire, he was panting enjoying my oral assault, little did he know what was to come. Standing again I pushed my crotch onto his and slipped his big rigid cock under the leg band of my panties, I watched with an open mouth as his mature shaft grazed against mine.
He lay down on his side pulling me down with him, facing him I ran my hand through his chest hair, I reached down to hold him. as I did he slipped his hand inside my panties. We rubbed each other and kissed on the forest floor.
“Fuck me” I whispered as I nuzzled his neck. Tony’s head span around quickly as though he had been slapped. “What? Really, are you being serious?”. “Yes don’t treat me like a child”.
He lay down and I straddled him, bending down I kissed him he pulled the lacy fabric to one side as he lined his cockhead with my hole.
“Are you…um ready down there”, I nodded. “Please don’t hurt me” I whispered between kisses. “Never” he replied.
He began.
Holding his hard shaft he rubbed his engorged head around my knot, he probed until he started to enter me, I gasped and tensed as his head broached my entrance. I sat and got used to this new feeling, a real live cock inside me. And it felt good.
I began to sit down on him and managed another inch, it was painful but not unbearable. “Talk to me Tony, tell me what a slut I am and what you’re going to do to me” I begged. His eyes were full of lust. “Im going to get my whole length into your boy pussy and fuck ever drop of cum from your balls”. God, hearing this made me hornier and more determined than ever, I went down again, then again I lost any sense of time until I felt his pubes tickling my arse cheeks, I was so proud, I had Tony’s cock fully in me and it was ecstasy.
I felt every ridge and vein of his hard cock as I began to ride him, the pleasure built and built as my rigid cock leaked pre cum over his hairy belly.
My palms were flat on his chest as I threw back my head and rode his magnificent cock, I felt so full, so sexy and wanted.
“Oh fuck David you’re so tight” he gasped as his cock rammed into me again and again, but I wanted more, I wanted to be truly fucked by my mature lover. I pulled off from him and felt his cock slide from me, he looked momentarily confused but as I got on all fours he grinned. “Oh yes Baby Boy I’m going to fuck you so hard you’ll never forget it” I loved the dirty erotic talk. I raised me arse into the air and suddenly and unexpectedly he pulled the knickers tight up my crack, with a rip they were discarded and replaced with his wet warm tongue, I squirmed in delight begging him to fuck me hard.
He knelt behind me and lined himself up with my gaping hole. “Do it” I begged him and boy did he. The niceties were over now discarded along with the knickers, he slammed all seven inches into me and fucked me with wild abandon, we were both groaning and the sound of his body slapping on mine was all I could here or care about.
Wave after wave of pleasure flooded through me as he fucked me naked on the forest floor, his hands gripped my shoulders as he fucked me without mercy, I felt my orgasm building and wailed “Fuck, fuck, fuck I’m cuuuuuuuming”. Hot ropes of cum shot from my cock, never had I cum so hard, I felt Tony tense, his grip became vice like and he moaned as his seed shot deep into my bowels, he had bred me and made me his.
We both collapsed into a heap, our sweat soaked bodies pressed together. As our breathing calmed down he looked at me. “Fuck, that was the best ever thank you”.
I rolled over onto him my back covered with cum soaked Autumn leaves and kissed him hard and deep. “Lets do it again” I whispered, he laughed and slapped my arse, hard.
“Tony?”, “Yes baby” “Have you ever had an all male threesome?”…