The MILF Chronicles – The Bagboy

The MILF Chronicles

The Bagboy

With summer gone, things returned to their normal rhythm. Days went by with my regular routine of work and exercise. I will admit that I found myself masturbating more often. The sexual power that I had experienced over the summer still reverberated in me and I found myself wanting more.

Unfortunately, with the weather growing colder, the opportunity to find hardbodied, willing young men declined as well. I was getting rather desperate and giving my fingers a good daily workout when I saw him.

It was just an average day, shopping for groceries, but when I got to the check-out, there was a new bag boy working. He was obviously older, not one of the acned teenagers that I was used to seeing working at the store. If you will pardon the cliché, he was tall, dark and very handsome! I was so intent on watching him work, his muscled arms lifting and bagging the groceries, that I totally missed when the checker gave me my total.

“I’m sorry, what?” I asked.

“It’s ok”, she said. “He has that effect on everyone, me included!” she said, casting a longing look over his way as he finished placing the bags in the cart.

I paid and with him following closely with the rattling cart, we headed out to the parking lot and my car.

“You’re a bit old to be a bagboy, aren’t you?” I asked.

“Yes, Ma’am”, he responded. “I just got out of the Navy and am attending the local Community College. This job gives me enough spending money and will work around my hours. Win, win I’d say.”

“Navy man, eh?” I said. “So is it true about having a girl in every port?”

He laughed. “Don’t I wish! I don’t even have a girlfriend.”

As he loaded my bags into the car, I stepped back and gave him the once-over top to bottom. He was a fine specimen of a young man. He would definitely do!

“Have a nice day”, he said after closing the hatch of my car, starting to walk back to the store.

“Oh by the way”, I asked, “Does the store do deliveries?”

“Yes Ma’am”, he said. “I am the delivery boy too!”

“I bet you are too” I thought as naughty thoughts spread through my mind and warmth spread between my legs. “I bet you are”.

As the weeks went by, I laid my trap slowly but steadily. Each week when I visited the grocery story, I made sure that I chose the line where he was working. Chatting with him, getting to know more about him. His name was Matt. Secretly I got to know the days he worked in the store and the days he delivered groceries. Now to bait the trap.

I waited until a Wednesday when I knew that he was working, I called in an order for some groceries. They told me it would be about an hour before they were delivered. I put on one of my sports bras and a pair of skin tight yoga shorts and sat my mat out in the living room. I began to go through my regular yoga routine, stretching and relaxing each area of my body, thinking about Matt and when he would arrive.

The doorbell rang and my heart skipped a beat.

Opening the door slowly, I could see a fleeting look of surprise and lust cross Matt’s face before it became neutral again. He was definitely getting an eyeful, as the bra and shorts didn’t hide much of anything.

“Come in”, I invited. “It’s too cold out there.”

Matt came inside with the bags and I led him to the kitchen, making sure that I swayed my ass as I walked.

“Yeah, but it’s really hot in here”, he said. I looked back over my shoulder and gave him what I hoped was a wicked smile.

“I’ll take that as a compliment:, ” I replied.

He placed the bags on the counter and took a long look at me. I could tell that he was checking out every curve and fold that was obvious in my tight clothes.

“Well, I better be getting back”, he said as he turned towards the front door.

I figured now was the time to go for it. I wanted him, if not now, then soon.

“Matt”, I said. “I hate to be so forward, but I was wondering if you would like to make a more personal delivery after you get off work.”

He froze in his steps and turned a quizzical look at me.

“Ma’am?” he stuttered.

“Well I know that we are both single, and I’m sure you have needs that aren’t being fulfilled. I just thought maybe we could help each other out.”

I was surprised at myself for being so brazen. Just a few months ago, I would have never dreamed of speaking to a man like this. It felt a bit scary and yet empowering.

He stared, his mouth open as if trying to find words.

“You do find me attractive?”I asked coyly with a big smile.

“Oh yes Ma’am”, he blurted.

“8 o’clock then?” I asked.

“Oh yes Ma’am!” he exclaimed as we walked towards the door.

I watched him go, but I noticed that he kept looking back as he drove away. I chuckled a bit to myself. It was so easy, and now I had him hooked. Not only that, but I was really looking forward to fucking his brains out.

I put away the groceries and finished my yoga, all the while thinking about how I would approach tonight’s encounter.

Was seduction needed? Flimsy lingerie, wine and candles?

Should I go full “Mrs. Robinson” on him and basically just have my way with him?

I spent a while in my bath, pondering my approach. I can’t be blamed if my fingers soon found themselves stroking my clit and sliding into my pussy. The anticipation of what was coming had me excited. One or two little orgasms wouldn’t hurt.

When I finally got out of the bath, the water was cold and I had lost count of my orgsams, but I had come up with a plan. In a bit of a compromise, I decided to wear my red silk kimono dressing gown that fell to just above my knees with a pair of red marabou pumps that I had bought on a whim. I hoped that this would be a winning combination of demure and slutty that would soon have us fucking like rabbits.

I put some wine in the refrigerator to chill, got out the glasses, and curled up on the couch waiting.

At precisely 8 o’clock, the doorbell chimed. I do love punctual men.

As I opened the door, Matt’s eyes traveled over my body and I could almost sense the hunger in him. It excited me to see that kind of desire in a man and I fully intended to take advantage of that.

I got us each a glass of wine and we sat quietly on the couch for a few minutes not saying much.

“Matt”, I said. “I want to see you naked!”

He almost choked on his wine at the frankness of my request, but a big grin spread across his face.

“Yes Ma’am”, he said, rising from the couch.

Matt made no pretense of a strip tease, just a methodological process of removing his clothes. Shoes, socks, then his shirt were soon a little pile on the floor. He stopped for a moment to look at me. I knew that he could see the same desire in my eyes that he had for me, I parted my legs slightly as a tease and encouragement, and leaned forward on the couch. The good stuff was about to be revealed.

He smiled, and his hands went to the buckle of his belt and the zipper of his jeans. Soon they too were on the little pile. There he stood in an old fashioned pair of boxers, which surprised me a bit. I guess I somehow thought that all young men liked underwear that framed their cock for presentation.

As he stood there looking at me and I at him, he said “Everything?”.

“Everything”, I responded.

His hands went to the waistband of his boxers and in one fluid motion, he dropped them to his ankles, stepping out of them.

Involuntarily, I heard myself gasp “Oh my!”.

Dangling between his legs was the longest cock I had ever seen in person. 9 inches at least and not yet hard. I could imagine what it would look like fully erect.

“Bring that here!”, I commanded.

As he stepped forward, I reached out a hand, encircling his penis, feeling the weight and thickness of it. It twitched in my hand and I could feel it beginning to stiffen as I held it.

“I can’t believe you don’t have a girlfriend with this beautiful cock”, I said.

He laughed. “Well it’s not like I can walk around with it hanging out as an advertisement”, he said.

I added my second hand to his rapidly swelling cock.

“That’s true I guess”, I responded. “But I must say that I am impressed”.

By now his cock was fully erect and I began to slide my hands up and down the shaft. His head, like a fat mushroom, was growing redder as I stroked him and I was overcome by a need to have it in my mouth.

Without warning, I sucked his big head into my mouth, my lips encircling it. He thrust his hips towards me in response, but I held on only to the head as I heard a gasp escape from him.

Sucking gently, I teased his head with my tongue. I swear it grew even larger under my attention. His cock now fully filled both my hands, even with the head in my mouth.

I slowly began moving my head down his shaft, removing one of my hands as I slid his cock deeper in my mouth. As I reached the fingers of my other hand encircling the base of his cock, his head bumped into the back of my mouth.

I had never sucked a cock so long before. Hell, I had barely sucked any cock at all, but I was determined to have all of this one!

As I drew back, I slathered my saliva all along the shaft, hoping the natural lubrication would help me to swallow this monster.

Slowly again I slid my lips down his shaft, a little further this time, feeling his cock pressing against the opening to my throat, Back and forth, a little deeper each time, his quiet moaning motivating me to greater depths.

Then as If it were the easiest thing in the world, my lips met the bottom of his shaft and I buried my face in his hair as I felt his cock slide into my throat. I heard an audible groan, and his cock seemed to swell again in me.

I knew he wanted to cum, and I wanted him to cum. I slid my mouth all the way back to his head and then down again all the way. His hands found my head, guiding, encouraging me, but I needed no encouragement.

As I quickened my pace, I knew he could not last much longer, so in one swift move, I buried his cook as deep in my throat as I could. His cock began to twitch and soon I could feel his hot semen spurting down my throat. I drew back, wanting to taste his juices in my mouth as his cock continued to throb, filling my mouth.

I looked up at him, his cock still in my mouth, enjoying the look of total ecstasy on his face. Removing my mouth, I swallowed his tasty semen, and stood up.

“My God,” he said. “That was fantastic!”

I reached out and grabbed his deflating, but still large penis, and led him towards the stairs and my bedroom.

“Oh, we’re not finished yet!”, I promised.

I led him by the cock up the stairs to my bedroom. Even though now soft, his cock was substantial in my hand, almost like holding a rope as I pulled him along. I controlled him with his dick. I liked it.

When we reached the bedroom, I led him to the bed and turned to face him. Without speaking, I unwrapped my kimono and let it fall to the floor. I let him feast his eyes on me. After a moment or two, I sat on the bed and lay back, spreading my legs wide, my marabou pumps furrily framing my slutty pose.

“Me!, I commanded.

Another look of pure lust crossed Matt’s face followed by a smile! He lowered his head between my thighs, gave my pussy an appreciative look and licked me from my asshole to my clit in one long slurp.

The shivers that went up my spine and the heat in my pussy were immediate. Matt began to work my pussy with his lips and tongue using long licks to draw my juices out and circle them around my clit. I could tell that Matt had eaten pussy before, because he was so good!

I was literally dripping as he slid his tongue inside me as far as he could and wiggled it about, curling it upward. My pussy clenched, trying to grab at his tongue as he drew it out, sliding the tip past my pee hole to find my very hard and throbbing clit.

My hands found his head. “Yes”, I said.

With his lips and tongue, he concentrated on my clit, gently sucking it and licking it. Swirling his tongue around my nub as she maintained a gentle suction. Flicking his tongue tip then a swipe with his full tongue. Round and round, up and down, sucking and licking.

My orgasm erupted in me like an explosion! My pussy clenched, my hips thrust upwards as I held his face firmly in my pussy. He continued to lick, more gently now, as my orgasm peaked and then began to recede.

He lay down on the bed beside me and kissed me. I could taste my juices on his lips. He playfully circled the areola of my nipples with his fingers, pinching first one then the other. They were as hard as stone.

My hand wandered down between his thighs and found that my nipples weren’t the only thing that was hard.

Taking my unspoken meaning, Matt moved down the bed, kneeling between my splayed legs, his long cock bobbing with anticipation.

Reaching behind me, he grabbed a pillow and gently lifted my ass, tucked it underneath me, raising my pussy to better accommodate him. Missionary position was pretty vanilla, but I knew that this was not going to be average sex!

My already sopping pussy seemed to leak even more juices in anticipation of Matt’s long cock and when he placed the fat head at my entrance, it was immediately wet.

Pushing into me, I could feel every inch of his cock as he slowly slid his length into me. I wondered if I could take all of him.

Almost at the same time, I felt the head of his cock touch my cervix as his balls touched my ass. I had never had a man so deep in me before. I felt totally filled and fulfilled at the same time.

He held still as if relishing the feeling. I pulled his face down to mine, kissed him and said, “Fuck me, hard!”

Matt needed no further encouragement. Quickly withdrawing his cock to the tip, he began to thrust into me like a piston. His quick strokes soon had me on the edge of orgasm again, but he slowed his rhythm and began long, slow, deep thrusts into my pussy. I could feel his head bottom out against my cervix at the end of each thrust as a heat began to gather in me like I had never felt before.

I was going to cum, but more than that, I knew that I was going to lose control completely. One more thrust pushed me over the top. My body began to shudder. My eyes rolled back into my head. My pussy began clenching and unclenching around his cock. I was a gasping, moaning beast, thrusting my hips up, keeping his cock as deep in me as possible.

Just as my orgasm began to ebb, I felt his cock throb and eject his hot semen into me. The feeling sent me right back into uncontrolled ecstasy, thrashing against the bed, thrusting against Matt, totally out of control.

He kept his cock in place as I came back to earth. His softening cock still filled me and I reveled in the feeling of fullness.

Eventually he withdrew and I rolled on my side so that he could snuggle up behind me. I could feel the heft of his penis pressing against the cheeks of my ass as he spooned me.

“That was nice”, he said.

“Nice? Jesus, that was fantastic!” I exclaimed.

I had begun this seduction with a feeling of power and control, but now I wondered if I were actually in control. Matt had made me lose it completely and I was consumed by the pleasure of his long cock.

I snuggled back against him and could feel that his cock was stiffening.

“Again?” I asked hopefully.

“Oh, yes Ma’am”, he replied.

Source: reddit.com/r/eroticliterature/comments/odkjnk/the_milf_chronicles_the_bagboy