My GF Got A Strapon Pegged PT4 free porn video

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This is the fourth in a series of stories of Cindy introducing her boyfriend to anal strapon play and fisting.

Who could have imagined that it could have all began with a single finger.

Cindy playfully stuck a finger up my ass and I moaned with pleasure. That was where it began. Soon we moved on to her fucking me with a strap-on, something I never imagined that I would enjoy. And then a larger strap-on and then ultimately her fist. My sweet and wonderful Cindy fucking me madly in the ass with her fist. And amazingly, I loved it all. Really loved it.

And little did I know, but we were just beginning.

Fisting. To say that I was addicted to fisting would be to use the wrong word. It wasn't a physical need exactly. I didn't need to be fisted, but I definitely wanted it. Not every night, but often. The intense stretching that wasn't quite pleasure nor pain, the overwhelming feeling of fullness, the complete surrender of having Cindy's hand and part of her forearm pounding relentlessly inside of me. It all felt so amazingly good.

But the most wondrous part of it all was the intimacy. The literal and figurative deep connection between two people, connected by lust and desire, but also by flesh, blood and bone. I cannot image any way to be closer to Cindy than having her hand and part of her forearm buried in my ass.

And Cindy wanted more.

One night, when I was on my back and Cindy was inside me with her hand and arm as deep as she usually could go, I could feel her hand moving around, probing, in a way she normally hadn't. The feeling was very intense. It didn't feel right. Suddenly, I felt almost frightened. I wasn't sure what was happening or what I was feeling. My breathing quickened.

"You OK?" Cindy asked. Her fingers pulled back slightly. The entire sensation charged and I felt calm again. Part of the intimacy of fisting is that it is also a partnership.

"Not sure," I replied. "Might be too much. I may need to take a break."

"Sure thing, love." She slowly and smoothly pulled her hand and arm back until her hand slid out with one last final stretch.

I rolled on my side and she laid down beside me.

"That was wild," I said.

"Did it hurt?" she asked.

"Not exactly, but the sensations were so strong that I felt kinda scared. What were you doing?"

"I had my hand part way in the opening of your second sphincter, the big bend where the rectum turns off toward the colon."

I laughed. "I just love it when you talk dirty."

She grinned, reached over and gave me a hard swat on my ass cheek.

She looked into my eyes. "Seriously, we should talk."

"OK," replied.

"I want to go deeper. I want to reach up and grab your soul."

"Speaking metaphorically, I'm sure."

"Yes," she smiled. "I have never gotten much further than halfway up my forearm. I want to feel my elbow slide inside your ass. I want to feel your ass lips on my bicep." She paused.

"How does this sound to you? We'll go slow and carefully. Would you being willing to give it a try?"

I have to admit, the idea of being impaled on Cindy's arm to her bicep was both exhilarating and scary as hell. Part of me wanted to say, "no, but thanks for asking" while another voice in my head was screaming, "yes, yes, yes." My rock-hard cock cast its own vote.

She was staring intently at me. I leaned over and kissed her then said, "Yes. Open me up. Let's go as deep as you can."

She reached over and grabbed the back of my head and pulled my mouth to hers, giving me a long and wildly passionate kiss. Then she whispered in my ear, "Let's give your ass a day's rest. Then we will get serious."

I had no idea what to expect. I only knew that I should get thoroughly cleaned out for whatever Cindy had in mind. As I gave myself several enemas, my bowels filling with a rush of hot soapy water, I tried to image what Cindy's entire arm would feel like deep inside me.

Later that evening, I waited naked for Cindy in the bedroom. She came in with a large bag.

"I've been shopping," she said with a grin. With that she pulled out a black silicone loop that uncoiled to become a slender but very long probe with a slight bulb at one end and a handle on the other.

"It is called a colon snake. Not very big around but 20" long."

"Well, OK," I replied. "Do you think I can take it."

Cindy smiled wickedly. "We are going to find out."

Cindy undressed. She reached for the lube and began to spread it on the snake and on my eager ass. I was on my back with my legs raised. She started to ease the snake in.

"Let's do this together," she said. "You'll know what you are feeling as we start going deeper."

I reached down and grabbed the slender flexible shaft and began easing it in. It felt good if very small compared to Cindy's fist.

Soon the head of the snake reached the top of my rectum and stopped. I pushed gently and felt pressure but it would go no farther. I tried pulling and pushing the snake in and out, and pulling to one side and then the other, but could get no deeper.

"Try rolling on your side with your knee bent," she suggested. "I've read that that may help."

On my side with one knee bent up to my chest, I started working the snake in and out and around again, maintaining a gentle but constant pressure until amazingly, I got the curve of the snake just right and it popped through the opening. The sensation was intense and I gasped.

"Are you OK?" Cindy asked.

"I'm fine. We are through the bend. Wow. What an amazing feeling."

I reached down and continued gently feeding the snake into my ass.

"This is so hot," Cindy said with a gleam in her eye. "You are into the descending colon."

She reached over and gently pressed on my abdomen.

"Feel this," she said. "You can feel the snake inside you."

With my free hand I pressed on my stomach and damn, there it was. The snake moving inside my intestine. I worked it in deeper and felt the head move closer up toward my rib cage.

I pushed deeper until I felt resistance. I had almost all of the snake inside me.

"You are probably at the next big bend, into the transverse colon," Cindy said. "We've done enough for our first attempt."

With that her right hand reached for her crotch. She starting rubbing her clitoris, slowly then faster. With her left hand she reached for the handle on the end of the snake and started gently pumping in and out of me.

I lay back, my cock newly hard, and started jerking as well. The combination of feelings was overwhelming, if slightly distracting. I came shortly after Cindy, our moans blending as we each caught our breath.

After letting my insides rest for a day, we played with the snake again. This time it was easier getting past the second sphincter. We tried it several times more and each time it was easier; my rectum seemed to be relaxing and getting use to the invader.

The next week, Cindy bought a longer, thicker snake. It almost felt as if we were starting all over again. It took considerable working and wiggling to get my second sphincter to open up for the thicker snake dildo. Nevertheless after a bit of probing and twisting, it made it through.

This time I didn't need to put a hand on my abdomen to feel the snake. I could see the bulge made by the larger toy as it slid up my large intestine. Watching the bulge move as I pressed deeper was both exciting and frightening. Cindy ran her hand gently over the bulge while twisting one of my nipples with the other. It was wild.

Just as with the other skinny snake, each time we played with the thicker snake, I opened up more easily. We managed to navigate the thicker snake well into my traverse colon. The bulge in my abdomen rose almost to my solar plexus.

Then, one night when I expected her to pull out the snake from the storage box under the bed, she instead appeared wearing her shoulder length red latex gloves.

I gulped.

"I think that you are ready. What do you think?"

"I don't know," I replied. "Only one way to find out."

Cindy rolled over a full length mirror and positioned it so I could watch her sink her arm into my ass. She then took the lube from the nightstand and started to slather it on one hand and arm, well past the elbow. She took her time, obviously for my benefit. It was beautiful, exciting, and frankly terrifying, all in parts.

She lubed my ass. She slid her hand halfway inside, palm up, and, poured a stream into her cupped hand, funneling the lube inside.

Then she slid her hand deeper. After having played with the snakes for several weeks, her hand felt huge. She pushed a little harder and my sphincter relaxed as if welcoming an old friend. Her hand and half her forearm slipped inside.

I was both participant and voyeur, watching the wild look in Cindy's eyes as she leaned into me while also seeing the image in the mirror her hand and half her forearm disappeared, as I savored every sensation.

I had expected her to immediately dive in deep. Instead, she took her time, playfully twisting her hand in my ass and running her knuckles over my prostate. If felt so good and I had not realized how much I had missed this as we worked on going deep.

Then after a few more minutes of play, the expression changed on her face. The devilish smile was replaced by a look of concentration. I could feel her hand groping for my second sphincter.

"One finger, She said as she ran a finger around the opening. "Now two." "And three."

I felt a fullness and an increased intensity that was both glorious and frightening.

"Four," she said quietly. "Now to tuck the thumb."

"Oh." I let out a deep gasp. It was overwhelming, a wave of sensation, almost too much to handle, that peaked and then passed. I caught my breath. My breathing slowed again and I lay very still.

"And we are in," Cindy said at little more than a whisper.

For a minute or two, she held completely still and then she pulled back slightly before pushing deeper. And deeper.

I felt an amazing stretch as her forearm disappeared into my ass. I was mesmerized watching the mirror as her forearm sank deeper, seeing and feeling every inch. She was getting close to her elbow now. She rocked her hand inside my intestine and I saw and felt the bulge in my stomach.

"How are you doing?" she asked.

"I'm wonderful," I said, amazed and exhilarated.

She pushed deeper. I watched her elbow disappear inside me. The stretch felt strangely pleasant.

She began to twist her hand and arm. "I am at the next bend, at the transverse colon. Tell me if anything feels bad." I nodded my head.

I felt pressure, not much. Mostly it was the strangeness of having another person so deeply inside me.

She took her time, turning and twisting slowly and gently. Finally she said, "Oh yes."

I looked at the mirror and she was well up on her bicep.

"Oh my god. Where is your hand now?"

"I can feel your rib cage, from the inside. Incredible."

She slowly drew her arm back, pulling back to just past her elbow. With her free hand she grabbed the lube and rubbed more on her upper arm, then pushed back bicep deep.

"Oh, yes. Fuck me," I murmured, overwhelmed and ecstatic.

I am not sure how many times she drew her arm out and plunged back in again. Her arm had become a part of me, a heavenly piston driving ever deeper. One thrust built upon the other until I was riding the crest of an otherworldly wave. It seemed to go on and on.

And then, in an instant, she pulled back and kept withdrawing her hand and arm. I felt her elbow slip free, the length of her forearm gliding out and then the final stretch as her hand slid free from my ass.

I felt exhilarated, exhausted and empty. I lay back looking up at the ceiling. Cindy get off the bed. I heard her removing her gloves. A moment later she was straddling me, holding my face with both hands, kissing me passionately.

She sat up. "That was amazing. How was it for you?"

"Beyond words. Fantastic. You said you wanted to reach up and grab my soul. I think you succeeded."

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WOW WHAT I DISCOVERED PT3 PT4

WOW WHAT I DISCOVERED – PT3I have been thinking I should do a character studY on each of these guys This guy's name is Peter known as PeteSince Chris shared his story to the group, we have had others of the group tell their story after an intense session or to fill in time.The next guy is Pete. Pete's cock is like a Boerewor sausage when deflated and 10-12 inches long when stiff and needs 2 hands to work it, and leaks precum like a dripping faucet Pete is 21 has been doing similar classes as...

3 years ago
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The house of Empress Toya pt4

The House of Empress Toya pt4   Myself & Belle have been receiving special attention since our last meeting with our Mistress. Extra fruit, wine (not normally given to slaves), extra food portions we of course shared this with everyone else. Although I am a slave my life has improved, I no longer have to work many hours a day on the land in all weathers. I sleep comfortable, I eat very well, I am always clean even my finger nails, and so...

Spanking
2 years ago
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A true strapon tale Part 2

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex, chastity play, and mild cuckolding.As mentioned in our last story Alex (29) and I (36) are both switches, and enjoy taking turns dominating each other. We had been dating for about a year now. Yet while we met other people here and there we'd usually spend the weekends together, enjoying each other's company and diving deeper into our passion for...

3 years ago
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My Wifes Strapon Surprise

It was another birthday about to have come and gone with little fanfare from either my wife or myself. It didn't really bother me all that much; I mean, thirteen years of marriage plus two kids tends to put a damper on your personal life events. I figured it would be pretty much the same as the last few, Melissa would give me a heartfelt card that I would appreciate followed by a hug and a kiss. Kids would be wrangled into bed, then I would download a new PC game as my gift and spend the night...

Anal
2 years ago
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My first strapon experience

I was a 20 year old college student who had broken up with my girlfriend of a couple years. We started talking and I had decided it was time to finally come clean bout my love for fetish. I told her I have had a dream that she was wearing a strapon and was fucking me and we both loved it. As time went on she got really into it and I told her my love for feet and my own cum. A week later and she was sending me pictures of herself wearing the strapon and playing with all the new toys she...

2 years ago
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The strapon experiment

(Contains F/M + Strapon!)The night was a night just like any other, a warm bed, snuggled up amongst the pillows, and that tingling that accompanied my fingers. I had been watching more and more videos as of late, and found myself yearning to try something that I hadn't done before. It seemed appealing, the men enjoyed it, the women did to, and it seemed just so...Fun. It took me nearly two weeks to build up the courage to go out and do everything I needed to do beforehand. I purchased a...

3 years ago
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Three Mature Ladies and Me strapon sex

hmmm a few months ago i was at a party of a friend and some older ladies were there too (family of his and acquaintances (around 30-45). Most of his friends were long gone after a couple of hours, but i was having a good time and having fun with the ladies.After a while the party was running towards it's end and some of the ladies invited me to go out with them and show them where i went out most of the time in amsterdam nowadays.Ofcourse alcohol was being consumed heavily on this night and...

1 year ago
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Brittanys Strapon Hell Week 5

I am currently working on #s 2, 3, and 4, but the idea for this one struck me, and I had to write it down, and I couldn't wait to post it! Please leave feedback, no matter how small. Enjoy! Brittany's Strapon Hell Week 5 By humbleslave I awoke on Friday morning to the sound of Mistress Brittany on the phone. "Yes, we'll be there to pick up the car at noon, thank you," she said. "Well slave, I decided to wrap up the conference early, so we can take a side trip. It's a surprise...

3 years ago
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Strapon escort

I broke down and finally called the number of an escort service I got online. I was very nervous having never done anything like that before. I had a very particular fantasy I wanted to indulge and thought this was the best way. A sexy sounding lady answered the phone. “As you might already know we specialize in making fantasies come true, so what are your fantasies?” She asked in a sultry sounding voice. “I … well … one of my favorite videos is ‘babes balling boys’ and I well …” I stammered...

4 years ago
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New Years Eve with the strapon milf next door

So I hadn't been over to the woman next door in awhile because about a month after our first fuck session she got a live in boyfriend who's there all the time. She and I would share glances every now and then but I figured that was it for our sexual relationship. But 3 days after Christmas I hear shouting from next door and they have a prolonged argument and finally he leaves and I see him with a suitcase and he screeches away. 3 days go by and I notice he hasn't come back so I go next door and...

2 years ago
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The first time crossdressed and strapon

The first Time Croasdressed and Strapon It has been 9 years since the first time being made in to a sissy for my then girlfriend. Her whole family was going away for the weekend so she said she want to stay home, here parents where ok with her stay home for the weekend and even told her to uave me over to keep her company when they where gone and enjoy the weekend together. Friday morning she came to pick me up telling me she had a very exciting weekend planed out for the two of us. So when...

2 years ago
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The Tea Shop Strapon themed

My first attempt at writing a story.I had answered an ad on-line for a local tea shop that was hiring. "Upscale Tea Shop Needs Milk Server - discretion is a must" read the add. Why would a tea shop need discretion? - I thought... I had not really intended to work at the tea shop. I just went in to apply for the job so, I could keep receiving my unemployment that I had been getting for the last 4 months. Really, I was lucky to get unemployment at all since I had been fired after being caught...

2 years ago
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strapon guy part 2

part 2this one is a little shorter but i'm trying to build a story here :)Still being a little lightheaded from the great sex we just had, I was reading a magazine on the kitchen counter. I was standing but I had to bend over a little because the counter was a little bit to low. I heard Linda (that's here name) walking towards me. I didn't pay to much attention to here because the articles where really interesting. Suddenly I felt something looking for my asshole. I looked behind me and saw her...

4 years ago
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strapon

. Here comes the story; I was meeting this woman through a internetsite. She was a lesbian, she claimed, but has always wanted to dominate a man with spanking and straponfucking she said that she wanted the man cry like a baby when she was finished with him.Well she took off my clothes and inspected me, pinch my ass and said wow what a nice little ass I am going to treat today. Eventually she went to the floor and laid me over her legs and then she began to spank me with her hand and she spank...

3 years ago
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Saturday strapon date night for my sissy

Every Saturday night I bend hubby over,lube up his ass/pussy,insert a butt plug,and start out with his punishment.The slapper is used 1st,It makes such a nice sound,slowly marking his white ass.I push on his plug,pulling it out,and back in until he is moaning.Next I use a crop to highlight the red in his rosy cheeks,Swat swat swat,Ohhh the sound of the crop swishing through the air hitting his crimson ass,I am In heaven.Finally,a ol fashioned thick wood paddle is used until the cheeks start to...

2 years ago
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A Shave and a Strapon

This story is a continuation of my previous story "A Buzzcut and a Strapon". Unlike the previous story which  was TRUE, this story is just a fantasy. My deal with Linda was more than a success: every week I would give  her a buzzcut and she would fuck me with her strapon. We were both very happy with it and had great sex. One Sunday, Linda woke up in the morning and she looked worried. "Ed, I have something to tell you. Listen to me." "What happened ?", I asked. "well, yesterday night I got...

Fetish
3 years ago
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Brittanys Strapon Hell Week 3 Fear with Jenna and Vanessa

Brittany's Strapon Hell Week 3: "Fear with Jenna and Vanessa" By humbleslave I am attempting to make these stories stand-alone as well as make sense in a series. If you like this, make sure to read my other stories. Think of your votes and comments as your contribution to my stories! Thanks! It had been a long week for me, and I had a feeling there was still a long way to go. After my humiliation at the hotel, the mall, and the college campus, I didn't figure it could get much...

2 years ago
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Sarahs Submission Ch 12 Conner Gets Pegged

Jenny talked to Amanda at school on Friday and invited her to join her and Sarah on Saturday afternoon to go shopping at the mall. Mr. Michaels, up to his normal tricks, got Jenny first and then later Sarah with their vibrators while they were shopping. At one point, Jenny had to lean on Sarah when it went on high for three minutes straight. Amanda noticed and asked if everything was all right. Sarah brushed it off as Jenny still being a little hung over from the party the night before. ...

2 years ago
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Did you like your Christmas Present Pegged

It was Christmas Eve.I was giddy with excitement; I was nervous as hell.I'd tried on the strap-on cock a few times and felt a rush at just seeing a cock poking out in front of me. I tried each cock, from the small, thin beginner weenie to the super cock and took selfies. I also put batteries in the vibrator one and tried it out, actually getting myself off with it. I had to agree with the saleswoman, this was definitely not something for a first time pegging! I would never be able to focus on...

3 years ago
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A Shave and a Strapon

This story is a continuation of my previous story ‘A Buzzcut and a Strapon’. Unlike the previous story which  was TRUE, this story is just a fantasy. My deal with Linda was more than a success: every week I would give  her a buzzcut and she would fuck me with her strapon. We were both very happy with it and had great sex. One Sunday, Linda woke up in the morning and she looked worried. ‘Ed, I have something to tell you. Listen to me.’ ‘What happened ?’, I asked. ‘well, yesterday night I got...

2 years ago
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Strapon Sally

Pete was a scientist in a Lab. He was on top of his field. He had taking in a helper name Sally who was a cute flirt. It turn out bad when Sally turn out to have a dominant personality. She would push him around He was now paying this woman for doing nothing. She was 18 years old and dressed in skimpy clothing. She would use his house and push him around. She also was a total tease. She had a tattoo of barbwire on her eyes. She had small dragon tattoo on her ass. She walked up behind him and...

BDSM
2 years ago
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Strapon Birthday PT2

After that wonderful birthday night, one that will never be topped for the rest of my life, our sex life and our overall life was better than ever. Both my wife Kim and I became happier than ever. We would constantly be walking around with smiles. Each of us was striving to be better, to look better, and feel better. We immensely loved my birthday night and our sex lives were changed forever.Over the next couple of months, regular traditional sex was slowly fading away. We had sex everyone...

4 years ago
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Strapon Lesbians

They had met in the bar of the hotel. A brief kiss on the cheek and a glass each of dry white wine before lunch. They ate sparingly, pasta and salads, but befitting the reason for them meeting, they drank nearly two bottles of a full bodied Rioja. Ignoring the glances of the other diners they wandered out of the dining room and over to the lifts smiling and nodding to each other. In the empty lift they kissed fully for the first time for nearly six weeks. Holding hands they walked down the...

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