On My Stomach Using A Condom (Challenge #4) free porn video

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In 2002 and 2003 when I was 23-24 years old, I decided to do a series of interesting masturbation challenges and I made detailed notes of the results. Here are the notes from one of those challenges:

Challenge #4 - On my Stomach Using a Condom for 7 Sessions.
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DATES: October 10, 2002 - October 27, 2002 LENGTH: 17 Days, 1 Hour, 35 Minutes

Challenge: To masturbate by rubbing/thrusting against a surface while lying on my stomach and using a condom for seven consecutive sessions.

Expected Difficulty: Moderate (Simple, Moderate, Difficult, Challenging)

Actual Difficulty: Moderate

Requirements / Restrictions:
- Must only rub/thrust my penis against a surface while lying on my stomach.
- May not stimulate my penis with my hands.
- Must use a condom and ejaculate into the condom.

Allowances:
- May touch my penis with my hands only when putting the condom on, taking it off, cleaning up semen, or while positioning my penis for thrusting.

Dates:
Session 1 - Thur. Oct. 10 4:54am - 39 mins - Very Good
Session 2 - Sat. Oct. 12 2:18pm - 32 mins - Very Good
Session 3 - Tues. Oct. 15 3:07am - 39 mins - Excellent
Session 4 - Sat. Oct. 19 1:52pm - 23 mins - Awesome
Session 5 - Tues. Oct. 22 3:05pm - 37 mins - Excellent
Session 6 - Thur. Oct. 24 4:41pm - 35 mins - Awesome
Session 7 - Sun. Oct. 27 4:32am - 57 mins - Excellent

Session Ratings (Highest to Lowest): Awesome, Excellent, Very Good and Good

Total Time of Challenge: Oct. 10 - Oct. 27 - 2.43 Weeks (17 Days, 1 Hour, 35 Minutes)

Observations:
I wasn't exactly looking forward to this challenge, I didn't think it would be very amazing, I knew it would be different and it was. In each of the sessions I put on a condom (as required by the challenge) to protect the surface I thrust against from semen stains and to make for an easier clean-up. I noticed that getting an erection took a few minutes in each session, and wasn't as hard as usual once erect. I also noticed I became very slightly less erect each time I was about to put the condom on. After I put the condom on I would use a tissue to remove most of the condom lubrication as I didn't want it to stain the sheets. In the first few sessions, I was still trying to find a good position and surface for penis thrusting. In the first and second session I was thrusting against my comforter while slightly on my right side/stomach. This felt alright, although I found my penis/condom would stick against the skin of my stomach too often making it uncomfortable. After that, in the same session, I tried thrusting directly on my stomach against the sheets on my bed, but again because of my penis/condom sticking against the skin on my stomach, it was too uncomfortable and I had to stop. I went back on my right side/stomach and thrusted again into the comforter, this time folded around my penis as much as possible. I tried to delay ejaculation for a while by using the start and stop method. Whenever the pleasure got so intense that I thought I would ejaculate, I would either stop or thrust very, very slowly. This is why the sessions were around 30 mins long.

In the middle of the second session, I heard a pop and felt a pressure change on my penis. The condom had broke and it exposed the head of my penis. I removed the broken condom, and put on a new one and went back to my session. I figure it was from the extensive friction and heat from rubbing it against my comforter/sheets for so long that lead to breakage.

In the third session I thought of a suggestion I read online of wrapping a T-shirt around your penis and thrusting into it, and I also thought of getting the spare soft fluffy pillow out of the closet and putting it under me, then taking a spare empty pillowcase (Instead of a T-Shirt) and wrapping it around my penis with the condom on. This would end the problem of my penis/condom sticking to the skin on my stomach. This worked extremely well, and I used it for the remaining sessions so for the third session onward, the rating of each session went from "Very Good" to "Excellent" or "Awesome".

In the fourth session, I got out the hand-restraint loop of fabric I keep in my drawer and I put my hands behind my back on top of my butt and put my wrists through the loop and pretended to be restrained there, as I thrusted my penis into the pillowcase and soft pillow. Sometimes the sensations I was feeling in the condom felt similar to how it feels to get a blow job. Especially when some of my pre-cum oozed inside the condom, making it slip and slide a bit when I thrusted into it. Other times I thought of the idea of having sex with someone, thrusting into their vagina or butt. I would often grip the pillows tightly and with each thrust, I imagined the expressions on my face as the pleasure increased. Expressions of desperation and ecstasy. I would often get sweaty. My face, arms, chest, legs and shins were sweaty. Sometimes I would have my face lying on the pillow facing to my left, other times I would have my head facing upward with my chin lying on the edge of the top of the pillow.

Sometimes the end of the condom would ride up a bit on my penis and the reservoir tip would even point in another direction and I would reposition it back to the proper place. For each of the sessions, I noticed that in the first 10-20 thrusts, there wasn't much pleasure, but as I continued, the pleasure increased greatly. I found that when the pleasure increased, my breathing became very quick wispy breaths and I felt close to ejaculation, so I tried breathing deeply instead and I noticed that the feeling of impending ejaculation was less, though the pleasure of the thrusts continued. When I ejaculated it felt different than hand stimulation because of the sensation of the condom tip area filling with semen and I could feel the warmth of my semen against the opening of my penis. I could also feel the veins in my penis pulsating around the base of the condom and sometimes it felt like the semen might be leaking out, but it wasn't. Also, the head of my penis became very sensitive after the first spurt of semen and so continued thrusting after that became so intense that I wanted to stop or slow my thrusting.

In the last session, I figured this would be the last time I would do this for a long time so I might as well try to make it the best one yet. I started by lying on my bed with my socks, underwear and shirt on. I did this by the light of the TV set to video mode where it shows only a blue screen, this provided just enough light. Starting like I do with my usual hand-stimulation sessions by pretending someone was dominating me. I took off one piece of clothing, then the next. I thought this would also help me gain an erection a bit faster. I whipped my underwear down a bit quickly as if someone else was whipping them down. I took off my underwear and it still took a few minutes to get a full erection. Then I put the condom on, and started the thrusting into the pillowcase wrapped around my penis on top of the fluffy pillow under me. I turned the fan so that it was blowing over my body, this caused a different sensation and it kept me cool. I started with speed setting 1 then I increased it to speed setting 2 half way through the session as I was sweating more. I got out the hand-restraint loop of fabric and had that on for a while, then I got the idea of trying anal stimulation. I got out one of the surgical gloves in my drawer, put it on my left hand and gently inserted my left gloved index finger into my anus. I tried feeling for my prostate, and I think I was able to glide my fingernail across it a few times because as I was thrusting and doing this at the same time, I felt like I was about to ejaculate, so I slowed my thrusting, sometimes stopping and continued a bit longer with the anal stimulation. I didn't use lubrication as it would have been messier and not easy to get to the bottle from this position. I pretended like my finger was a penis thrusting in and out of me. After a while, I was eager to get back to regular thrusting, so I took my finger out and took the glove off. As I was thrusting, there were times when it was uncomfortable and even slightly painful and I had to reposition my penis. Later in the session, I was nearing ejaculation, so very, very near and I actually had just started ejaculating when at that moment, I felt that the condom probably broke. I didn't want to stain the pillowcase with my semen, so I stopped all thrusting and tightened my PC muscles to try and stop the ejaculation in mid-stream. I was partially successful, though when I pulled my penis out of the rolled up pillowcase, I noticed that I did get a good amount of semen on the pillowcase. I wiped it off with a tissue, took off the broken condom and put on a new condom. I still had my erection and was still horny to continue with my session. I started thrusting again for a bit longer, then I thought that this had lasted long enough, I was happy, so I allowed myself to ejaculate again and it was pretty intense. I basically got two ejaculations for the price of one which is extremely rare for me. The orgasm of the first ejaculation wasn't as intense as the second one.

I have to note that there were a couple of times when I broke the rule of "No touching my penis for stimulation", but they weren't during an actual session. Once I played with my erect penis briefly in bed when I woke up, and another time I took my erect penis out of my pants while sitting in my computer chair and mostly stared at it or touched it briefly.

Conclusions:
I found that at first, in the first few sessions, I couldn't really get into it until I found a method that worked well for thrusting pleasure - the fluffy pillow under me with an empty pillowcase wrapped around my penis (with a condom on). From then on, I was able to get into it more. From the third session onward, with the discovery of this optimal position, the ratings went from "Very Good" to "Excellent" or "Awesome". I noticed that I longed for hand-stimulation and that at times, I just wished I could get this challenge over with so I could go back to hand-stimulation and my standard fantasies which I found difficult to use in this kind of thrusting-type masturbation. I found that with extended thrusting onto fabric, the friction and heat sometimes causes the condom to break. An experience I would not want to happen during actual intercourse. I now have a better idea of how fragile a condom can be. I found that using the stop and go method I learned in hand-stimulation worked well with thrusting too. It really prolonged the sessions and at times the pleasure was very intense.

Being in the position of lying on my stomach and thrusting like this added a new dimension to masturbating. It didn't feel like masturbation as I knew it, it felt closer to what having sex would feel like. I felt different emotions. I felt vulnerable, I felt "close" to the pillows I was thrusting against, as though I were part of them, inside them. Feeling the air across the back of my legs and butt and with each thrust, feeling them rub against the sheets, it felt very sensual. This type of masturbation is probably the closest technique I have ever used to what intercourse would feel like. That said, I noticed I longed for hand-based stimulation and wanted this challenge to be over with, though from time to time, I might like to masturbate this way.

Would you do it again? Recommendations:
I don't think I'd care to do this challenge again.

I would recommend that the optimal position/technique I found could be improved upon by adding lubrication somehow, although this would be more messy, it would also probably reduce the chance of condom breakage and increase pleasure.

Challenge Status: COMPLETED, MET CHALLENGE REQUIREMENTS
MAY HAVE BROKEN A RULE - Read last paragraph under 'Observations'


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There was a time when my wife's gynecologist advised her to stop taking the pill for three months. My wife asked her about sex and the doctor said that there would be no problem if we (myself and my wife) used a condom!! Problem!! 1) My wife hates condoms, and 2) My wife was fucking this black stud every two or three weeks, for about 2 years and had not seen him in a few weeks. He would be out of town for another two months and we were scheduled to spend a three day weekend at his place when...

2 years ago
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No Pill No Problem Condom Breaks Blacken

There was a time when my wife's gynecologist advised her to stop taking the pill for three months. My wife asked her about sex and the doctor said that there would be no problem if we (myself and my wife) used a condom!! Problem!! 1) My wife hates condoms, and 2) My wife was fucking this black stud every two or three weeks, for about 2 years and had not seen him in a few weeks. He would be out of town for another two months and we were scheduled to spend a three day weekend at his place when he...

1 year ago
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Sex with China lady Sex with condom becomes great sex without condom

i had the wonderful opportunity very similar to my earlier story in wuhan. i was in dongguan, china and visited a massage parlour. i like young masseaus, especially inexperienced ones. a young lady in early twenties served me. it was only her first week of work in this industry. i offered to tutored her how to give sensual/sexual massage. she obliged and i started to work my hands on her body freely. she was faced down and my hands worked on her back, buttocks. soon, i moved into the inner...

Erotic
3 years ago
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Her Last Time Asking for a Condom

The first days fucking Ashlynn I wore a condom every time. The sex was great. We would fuck for hours. She orgasmed again and again. I did not cum. This is something that I had grown to accept as part of my sexual experience. Sex without a condom would take hours for me to climax. Sex with a condom certainly meant I was not cumming. Ashlynn was a typical type-A neurotic overachiever. She did not like giving up control. Not on birth control, she certainly would not risk having unprotected...

True
3 years ago
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The Slut Challenge

It's been 6+ years since I've been to a swingers club. Finally, I set up a date when I want to go. Saturday was a special day for me and I wanted to celebrate this way. My Owner allowed me to go, but for a price of a Slut Challenge. I was to invite home a record number of tinder dicks in one day. During that time my Owner would be hidden in a house, hearing me moan and scream of pleasure. He would fuck me in between the fuckers too. The idea sounded amazing, I was so excited to do this!I...

1 year ago
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Black Bull Challenge

…and welcome one and all one of the best website reviews you will ever read!As I recall, it was around the middle of the aughts when I noticed that a few categories and presentations of porn became super popular. The most obvious was gonzo porn, but as time wore on, a lot of other people and I noticed that interracial erotica blew up in popularity.In hindsight, I cannot say that I am super surprised – especially the way this trending type of erotica was presented. Plenty of scenes would and do...

Premium Cuckold Porn Sites
3 years ago
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Twelve CondomsCondom 3 Nancy The Hurry Burger

It was a common practice for Sam to drive down to the Hurry Burger on his lunch breaks. The food was cheap, the service fast, and the cashiers cute and flirty. This time however Sam didn’t turn into the Hurry Burger’s parking lot, but instead parked in the empty bank lot next to the fast food joint. In his head Sam had a mental list of all the women he wanted to fuck and top on that list was a lesbian tease by the name of Nancy Gibson. Unlike the other women on his list bagging Nancy would...

1 year ago
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Twelve CondomsCondom 5 Bridget Taboo Lust

At his age family outings were a rare event for Sam. But the Landing Family still did get together for the occasional weekend excursion. Which is how Sam found himself on a nature hike with his cousin Bridget. Her hot body leading him up and down the narrow pathways of a forest reserve. Watching Bridget’s ass sway back and forth in her tight jean shorts was giving Sam some very naughty thoughts indeed. And from time to time Sam found himself fingering his billfold as he considered the magic...

3 years ago
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Condom Karl

Radvany Carl graduated high school top of her class at age 17 and was picked by the state university on a cheerleading scholarship. The campus was two hours from home so her folks found her a dorm room. Her 18th birthday would come two days before Halloween which meant that her first 6 weeks as a college student she was still 17. Her grey eyes and raven hair and petite athletic build with breasts that were ample for her figure but had no sag that needed support and rump that made the...

2 years ago
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ST Broken Condom Part 1

Broken CondomBy Tom Stone ~ [email protected] is only a story. I encourage you to ALWAYS engage in safer sex; wear acondom; wrap your willy, etc etc."Choosing safer sex for you and your partner greatly reduces the risk ofcontracting STDs including HIV -- you can get answers to your safer sexquestions, courtesy of staff members at the SF city clinic"Do not read this if you are u******e or it is i*****l to do so in the areain which...

3 years ago
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the white boy pussy challenge

''apparently she caught him in panty ....can you imagine how weird it is''''just a challenge he said he lost , but how weird is that...a boy wearing girl panty''''I really dont know Marie but its weird indeed''i was back from school and mum was with her friend Marie, trying to avoid them, as they talk about my friend Brian''hey Alex how are you, had a good day?''''yes....im tired tho''i went up and changed , removing my cloth i was quick to remove my little panty , i was one of them....it went...

1 year ago
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Master PC The ProtectorChapter 41 First Challenge

I froze. The white napkin was still clutched in my hand and I hadn't so much as drawn away from the sight before me. I was expecting many different things. What I saw was so far removed from what my poor brain had tried to prepare me for. There was no way to hide my expression. Some of my girls were looking, but none of them were saying anything. I didn't blame them. They had let me do all the talking because Vikkor, Law and Chaos seemed to be more interested in me as a Master PC user, but...

1 year ago
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Magnum XL Condom Girl

Neither of us planned it that way, but my most beautiful friend got fucked by two different guys with enormous dicks, once when she was just 18 and once seven years later — and I got to watch both times! It all started when Becky and I were freshman and decided to join the same sorority. We were each assigned a different “initiation project.” The girls concocted a rather interesting assignment for Rebecca, because she seemed so innocent, even for a freshman. They demanded that she try to seduce...

3 years ago
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The Challenge

The Challenge Author's Note: I know it has been a long time since I've published anything but I have been stuck for ideas. I started on it, let it slip aside for a while, then saw some new comments on some old stories and it inspired me to get back to it. I hope this one is worth the wait. Joe reached down the side of the recliner and pressed the button that would drop the footrest and return the back to the vertical position. "What do you think, Babe," he asked as the chair...

3 years ago
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My Single Greatest Challenge

Copyright© 2001-2003 There once was a gaucho named Bruno, Who said, "About sex, well, I do know, Sheep are just fine, Chickens, divine, But iguanas are Numero Uno." It was a simple question but I felt my heart pounding in my chest and froze with a stupid open-mouthed gaze. Mom looked from grandmother, her mom, to me and back again. My frozen stupidity only lasted a mere couple of seconds but it was long enough for me to realize that mom knew something was wrong. For two...

3 years ago
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Stranger Sabotaged the Condom

A few years ago I was being intimate with a man we had met at a party. My husband was there watching and things were going pretty good except for a few snide remarks the man-made once we were both naked and on the bed. This guy had the wrong impression that my husband wanted to be humiliated by him since he was allowing him to "fuck his wife." He let things slide and didn't say anything but just watched silently. The man must have taken this as approval of what he was doing because he then got...

1 year ago
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Stranger Sabotaged the Condom

A few years ago I was being intimate with a man we had met at a party. My husband was there watching and things were going pretty good except for a few snide remarks the man made once we were both naked and on the bed. This guy had the wrong impression that my husband wanted to be humiliated by him since he was allowing him to "fuck his wife." He let things slide and didn't say anything but just watched silently. The man must have taken this as approval of what he was doing because he then got...

4 years ago
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Condom Fata Bhabi Chudi

Hii.. Mera name vaasu ha.. Meri age 20 ha.Mera luund 8inch lamba ha. Agar aap ko meri help chahiye to Email Aap ko pura maja mile gaa..Kisi bhi woman,girl,aunty, sab ko sukh du gaa paka … Aapko apne pahle sex ki story batane jar aha hun jo ki maine apni bhabhi ke sath kiya or yakinan ye aapko pasand aayegi . Meri umra abhi 20 saal ki hai or main pahle apni family ke sath bhopal mai rahta tha or mere mama ji ke bade bete or bhabhi bhi hamare paas mai hi rahte the. Hamare paas 2 bhk ka flat tha...

3 years ago
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The Emperors New Condom

I couldn't keep doing the Sears catalog, not if I wanted to be somebody someday, or something. I had to keep moving up, that's what my agent kept saying. Since he was also my dad, I pretty much listened to him, but this seemed kind of weird. "A condom commercial?" I giggled because condom struck me as a funny word. I'd never actually seen one in my life. "Commercial," he agreed. "That's the key word. It's a big step, Wendy." "I'm only fifteen," I reminded him, whispering...

1 year ago
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The Challenges

The Challenges by AtomicWriter Everything in this story is fictional, do not read if you are under the legal age for reading adult fiction in your place of residence. "I don't know, that seems kind of unfair," Kyle said skeptically. "You don't think you can win, do you?" his sister, Jessica asked back. She smiled that annoying smug smile, the same one she always had when she teased him. "I didn't say that, it just seems like the bet makes it very easy for you to get what...

3 years ago
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Condom Failed Another Black Baby

Hi my name is Tami, I grew up in an all white town. My father was a hateful man who did nothing but rant racist bullshit whenever a person of non white origin stopped in for repairs at his garage. My father was two faced, he was nice as could be to everyone face to face but the minute the repairs were done and they were gone the shit poured out, Why don't those spics, niggers, asians all go back to their own countries." I could never understand why my father was so hateful after all the white...

3 years ago
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Male Virgin Condom Breaks

She jumped on after me, those moist lips hovering over my crotch as she pulled my trousers and boxers down around my ankles. She kissed my cock and as her lips touched me, I knew that I was about to get my first blowjob, I was sure of it. Her lips were so soft, I daren't imagine what the inside of her mouth would feel like.'What's it to be big boy?' She said, pulling a condom out from somewhere. 'You want to feel everything or feel safe?''Won't the condom taste bad?' I asked, it didn't look...

3 years ago
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Dottod condom

Hi friends yeh meri pehli story hai aur yeh meri real story hai jo me aap logo ko batana chahta hu. Ek din me barbar ke waha baal katane ke liye gaya tha , dopaher ke 3 baj rahe the, barbar shop band karne jaraha tha ,usi samay me pahuch gaya , usne mujhe under liya aur shop under se band kardiya aur kaha ke tumhare baal kantke khana khane jaunga Undar sirf hum dono hi the ek dum sannata tha , woh mere baal katne laga. Baal kat te samay uska lund mere hath par lag raha tha aur erect ho chukka...

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