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cityboy1969 46 M
1  Article
First time threesome with 2 Hot Italians   5/1/2006

Summer of 1990, I was 21 then and not out of the closet yet. For the summer holidays I was traveling with 3 of my mates through Italy by car. My mates were all straight, so it was going to be a long, lonely holiday.
We decided to stop at Lake Garda for a few days and put our tents up on a nearby camping site. We went out a lot in the evenings and were hammered during the days. ...


0 Comments, 1034 Views, 33 Votes ,7.83 Score
tvdonna 47 T
1  Article
First date as Donna   4/27/2006

I have been cross-dressing for a number of years. Recently, I have been joining various chat rooms devoted to cross-dressing. One night I started chatting online with another CD, and she told me she was into "masking" - using latex female masks while dressed up. I had heard of this before, and was curious about it. We agreed to meet the following weekend so I could try the masks out for ...


1 Comments, 1107 Views, 34 Votes ,4.77 Score
hotplaymate4u 64 M
3  Articles
Very True Encounter   4/27/2006

I am so happy, I want to share this with all of you... Yesterday was a beautiful warm day, so I decided to take the day off at my private fishing spot... I was there fishing for an hour and heard something coming through the bushes and it was another fisherman about the same built and age as me, average and 50's of age... He sat up his gear and sat a few yards away from me... after 30 ...


6 Comments, 2178 Views, 76 Votes ,8.14 Score
Bebeji 69 M
2  Articles
First Black Cock   4/14/2006

I have been on Outpersonals for a while. I met this HOT Black man on here. He invited me to see his cam on Yahoo. WOW!! He looked huge. We finally got together one day and I was NOT disappointed. I am 7" cut but him...wow...he is at least 9" and fat and soooo hard. we took each other in our mouths but I could only get about 2-3" in my mouth. I NEVER thought I would be able to take suck a ...


7 Comments, 2134 Views, 43 Votes ,4.52 Score
2curious47 70 M
2  Articles
First Anal   3/19/2006

I am not sure if this should be here or under "Success Stories", but after many years of fantasizing about it and watching videos, I have finally had the pleasure of anal sex. After being an OP member for a while, I met someone who was willing to accommodate me and show me what it is really like to have a man inside of me. I was fully prepared, thanks to much advice found on OP. ...


2 Comments, 1578 Views, 27 Votes ,2.71 Score
mikee469 36 M
2  Articles
Firsttime jitters   3/13/2006

I met Joe on Outpersonals a couple years ago. I had no experience at 27 but was very curious and online seemed the way to go. He was 62 and retired! I love em older!! We chatted online a few times and then talked a few times on the phone. He knew I was a virgin and he didn't push anything. I really wanted my first taste and we set a date. As I pulled into his driveway, I was so ...


1 Comments, 1587 Views, 45 Votes ,8.12 Score
pleaseu1948 68 M
2  Articles
becoming a slut   3/13/2006

it had been a long drive and as i neared the state line i saw the sign for a rest area. it was about midnight and i was tired, so i pulled in to get a few hours sleep. i parked the pick-up and just leaned back, when a car pulled in next to me. as i sat there i saw a young black man, in his 20s, start to play with himself. he opened his pants and pulled his cock out and started to stroke it. ...


0 Comments, 1728 Views, 41 Votes ,6.45 Score
funnt200555 54 M
2  Articles
Virganity Lost 2   3/5/2006

First we lick the body of each other under shower.Our hard cocks were playing love game by fighting each other.Then my friend started licking my bottock.It was quite new for me and extreemly full of lust.Meanwhile he started fingering.Oh it was flying me up in the air high and high.Also he performed a very new thinge he put some oil on his cock and asked me to bend in front of him. He ...


0 Comments, 593 Views, 10 Votes ,2.99 Score
lovemybutt 59 M
3  Articles
My First Time with a Guy   3/5/2006

I met the first guy I did it with through some voice personals as I didn’t have a computer at the time. Chris was an Asian guy a few years younger than me, a rookie like me and luckily for me, he was interested. He said he’d only been with two other guys. He was wearing jeans and a tee-shirt. I found him quite attractive and he had lovely smooth round Asian arms which is a particular ...


1 Comments, 1376 Views, 23 Votes ,5.93 Score
funnt200555 54 M
2  Articles
Virganity Lost   3/4/2006

I and my partner were class fellow too.We were lover of each other.It were the days when we were of 13 to 14 years.When ever we got chance, we made love with each other.That was consist of kissing , licking the whole body.Fucking was consist only putting the head of cock on asshole and forced it for penitration.But we were unaware about the use of lube. So penitation in such a tite ass ws ...


0 Comments, 775 Views, 11 Votes ,3.17 Score
ohboy192 29 M
4  Articles
your first time   2/28/2006

i have never had anal.. how bad does it hurt? anyone have interesting experiences with there first time let me know.. and maybe you can be mine...


5 Comments, 1080 Views, 8 Votes ,3.25 Score
ohboy192 29 M
4  Articles
first date sex   2/28/2006

is having sex on the first date wrong? hit me up with your answer


0 Comments, 299 Views, 0 Votes
lovinglife4 43 M
1  Article
First Time   2/23/2006

Well I have only been with one guy before. He was my best friend when I lived up in New York. I have always been attracted to guys and have always had to hide it do to my career. Well me and my best friend went to a house warming party one day and boy was it a party. People getting drunk and doing all kind of crazy things drunk people do. Well the party started dying down and people were ...


2 Comments, 1410 Views, 33 Votes ,5.81 Score
Twiggy1968 54 M
2  Articles
Hot Sex on the First Date   2/19/2006

I'm 37, married and have never been with a man until recently. I met him online and went over to his house. We had so much in common. We sat talking on the couch for a while. He made several comments that led me to believe he was ready, so I told him if he wanted to have sex, just say so. <br> He'd had a bonner for sometime, was his answer. We undressed slowly, admiring each ...


0 Comments, 1491 Views, 28 Votes ,3.55 Score
bookmage 55 M
1  Article
My First Male Massage!   2/18/2006

The only truly bi-sexual experience I've ever had was with a male massage technician in Houston. He professionally gave massages during the day, but by evening, he offered a "complete male massage." I called him several time, corresponded by e-mail a few times and finally convinced myself that he wasn't going to murder me or me. When I got to his place, he had the massage table set ...


4 Comments, 1487 Views, 29 Votes ,5.25 Score
sexonly112 48 BC
21  Articles
Bottom Looking for Top   2/16/2006

I am a bi-curious virgin looking for first time. For years my wife has a strap-on and a large assortment of dildos that she uses on me. My favorite sex and position is when she has the strap-on and gets on top of me, the feeling is unbelievable. She has literally fucked my ass for hours at a time and I just can’t get enough of it. I am looking for a top guy with lots of stamina and ...


3 Comments, 593 Views, 9 Votes ,3.43 Score
TitianLover 36 M
1  Article
All I know...   2/14/2006

All i know is that when im on a date, a first date that is, and then offer to pay the entire thing, then i expect the other person to offer to pay atleast half if no the whole thing. that way, if hes lucky, ill have money to buy desert later.....


1 Comments, 495 Views, 10 Votes
BlackRussian 63 M
34  Articles
Here's A Great Idea For That Romantic Date   2/13/2006

O.K. Some of you who have written to me in the past may have already heard this so I'll warn you. <br> Several years ago I took a trip to Cancun, Mexico. I love Mexico and I'd been to the West coast of Mexico many times before this; Puerto Vallarta is my favorite and I've been there at least 6 times, but I also love Cabo San Lucas and mazatlan. <br> Anyway, Cancun was ...


0 Comments, 278 Views, 4 Votes ,0.92 Score
BlackRussian 63 M
34  Articles
Some Great Tips For First Dates   2/10/2006

Some people have written in frustration recently to ask why it is that often they do not get past a first date with new guys. <br> It makes one wonder, is it the men today? Is there something wrong with me? Is my approach wrong? Why is it that I never seem to get past the first date with guys? <br> The first thing to remember is that you cannot please all of the people. ...


0 Comments, 430 Views, 10 Votes ,6.17 Score
tundra1956 63 M
1  Article
First 69   2/7/2006

I had had a few blow jobs from men before in XXX shops but had never sucked a cock. I met a guy on-line and we chatted several times. He had seen me on cam and wanted to suck me. We decided to meet at my place early one Sunday morning. He was new to bi sex and I had never really "been" with a man either. After he got to my place we talked for a couple of minutes, then he asked me where ...


1 Comments, 1202 Views, 34 Votes ,5.31 Score
surpriseme1 62 M
1  Article
I wonder what Walters doing now   1/26/2006

I can't remember how it started. We were what, fourteen, fifteen, whatever; the age when sex invades your head and everywhere else. We travelled to school on the train, a steam train, one of the last in England, that shows how long ago. We'd pray for the type of carriage with separate compartments with no corridor in between, absolute privacy. Morning and evening we'd be together alone ...


1 Comments, 1076 Views, 24 Votes ,5.29 Score
Crazy4It2 60 M
1  Article
First Blow   1/21/2006

As I was working on my car out in front of the house I noticed a car pull up and heard you say, are you Crazy4It2? I look up and say, yes...why are you too? You nod your head and I walk over and get into your car. As you start to drive away, I reach over and unzip your pants and pull your stiffening cock out and bend over and stuff it into my mouth. I keep it in my mouth and feel it ...


1 Comments, 1340 Views, 34 Votes ,3.78 Score
LisaNJcd 68 T
17  Articles
the funeral   1/18/2006

This next story occured after my uncle passed away. My Uncle Paul, who I was very close to (no, not sexually) had died and I had every intention to attend the viewing and funeral, which was 120 miles away and in another state from my home. I had been chatting with a man online that lived about 30 miles from where the funeral was to be, and I emailed him with my phone #, telling him that I ...


2 Comments, 1364 Views, 22 Votes ,4.21 Score
LisaNJcd 68 T
17  Articles
after my date   1/18/2006

This is frustrating....I had the next chapter almost ready to post and then we had a power outage, so I called a friend and asked him to come over today for some one on one fun. I will do my best to complete this and get it posted as I wait for him. After my accountant left, I got re-dressed in my tight mini and low cut top, freshened up my makeup, and went back to the gay bar where I ...


1 Comments, 834 Views, 25 Votes ,6.78 Score
Lance20005 72 M
2  Articles
Unrequited (almost) love   1/17/2006

This is a true story. <br> When I graduated from college and moved to Chicago I ended up rooming with a fellow recent graduate. He was fairly attractive physically but extremely attractive emotionally. We had our share of good times but never anything sexual. <br> A few years later, I got married. We ended up travelling somewhat together with our jobs. During this time, ...


1 Comments, 1004 Views, 23 Votes ,5.58 Score
LisaNJcd 68 T
17  Articles
next   1/17/2006

The party at the VFW was actually the day before the actual holiday, and since my wife didnt like seeing me this way, we didnt have sex that night, not that I wanted to anyway, I had too much fun with my friend in the car. But I did stay dressed for the next day and stayed home to pass out candy to the trick or treaters. Surprisingly, I didnt receive any negative comments from parents or ...


4 Comments, 923 Views, 30 Votes ,5.59 Score
LisaNJcd 68 T
17  Articles
Halloween Party   1/17/2006

Halloween...1991 My wife and I were asked to attend a Halloween party with some friends at the local VFW, the same one we attended the year before and won first place for most original costume, which I had chosen. We were the Pope and she was the devil. She asked me to pick this years theme, and since I had gotten more into my crossdressing, I wanted to go as a woman....naturally. My wife ...


1 Comments, 1044 Views, 27 Votes ,6.19 Score
LisaNJcd 68 T
17  Articles
gloryhole adventure   1/17/2006

As my marriage became progressively worse, my crossdressing became progressively more advanced. I began to wear at least panties under my male clothes almost every day, but was reluctant to do so at work in case I were to become injured and had to go to the clinic or thinking they may be seen if I bended over the wrong way. Sex at home with the wife became less frequent and less enjoyable ...


4 Comments, 1472 Views, 40 Votes ,6.19 Score
LisaNJcd 68 T
17  Articles
where to begin??? hmmm   1/17/2006

My first m2m experience occured when I was 15 with a neighbor who was in his late 40s. It was just a mutual JO session, but I enjoyed it and went back to him several times for more of the same. Became interested im girls a year after that and married at age 19, but still thought of men, and wanted to explore further and learn to perform oral.Had many opportunities thru-out 2 marriages, but ...


0 Comments, 1057 Views, 18 Votes ,4.63 Score
mhuntu 65 M
1  Article
Old friend gets a surprise.   1/14/2006

I have always felt since I was 13 years old that I was attracted to man to man sex. When the neighbor boy talked me into showing him my cock with the old line of "I'll show you mine if you'll show me yours." Well I did and he did but then he touched me and I grew rock hard in an instant. He noted that I had a large cock as his was only about two thirds the size of mine, he wanted to ...


2 Comments, 1906 Views, 42 Votes ,5.93 Score