I cannot get over how my life has changed in the last three months. My best friends and I have all had girlfriends on and off through high school; we each lost our boy-girl virginity early. My name is Evan, and my best friend buddy, and bro is Matt. We have been inseparable since kindergarten. Matt & I have done everything together for about 15 years except sex…well, then again…maybe sort of! Ha ha ha.
My " bestie bros” (Matt mainly) and I practically lived in my teen-boy-basement pad (TBP). It was a super cool teen hangout. Seeing as my parents were high-profile doctors, Mom a psychologist, and Dad a Cardiologist, we were blessed with a more comfortable family income and gorgeous home. I worked part-time for about 15 hours a week over three short shifts on weeknights, Tuesday to Thursday, in a local grocery store, stocking shelves and hopping from department to department wherever I was needed.
The (TBP) basement teen boy pad was built for me as a birthday present from Mom and Dad. I am an only child, so I have no siblings, and none are planned. Mom and Dad never said why. I do not care because I had many awesome guy friends. Matt was the best. My first girlfriend was Lisa. She was beautiful. We both finally had sex on the leather couch in this very basement a few years ago. Yes, we all used condoms all the time for all our girl fucks. She had trouble sucking my cock and complained in every position of sex that my huge penis struck the cervix.
I always wanted it even bigger, but at 18, it clocks out at a very happy 8.5” long and about 6.5” around at the base. Lisa would not swallow my cum either; I kept begging her to, but she never would. I ate it sometimes in front of her, and I thought it really tasted good. She thought it was gross.
All my friends and I are circumcised, as were most of the boys in our high school; this was evident in post-gym and sports showers. It is so much fun showering all naked with other teen boys, all of us half hard or even full erection, whatever state of arousal no one cared. We were all being taught and inundated with the open sexual orientation and human sexuality that said the law and society saw it as acceptable and usual to fuck anyone of any gender and identity; there was no real bullying of any sort related to one’s perceived or actual sexuality. Deep down inside my head and soul, I was longing to try sex with a boy.
During doggie-style fucking with Lisa a year or so ago, I took a chance and porked her up her asshole without any notice or consent. It was wrong of me, and I apologized! She did experience some pain and a bit of pink, but the tightness and eroticism of it had me overflow the condom with, at that time, one of the largest cums I had ever had. There was a bit of shit, but it turned me on even more. She broke up with me a week later and started dating a nerdy twink named Billy, who we all saw in the showers had a below-average cock of 5.5” and was always fully hard. Lisa just wanted a more comfortable penis. I moved on to Rachel, then to Stephanie, and had the same issue with my size and wanting anal sex with them. They all broke up with me, and I reverted to jerking off in the basement.
God, I loved this basement. The large rec room had two leather pullout sofa beds and four comfy big leather chairs and hassocks. There was a galley mini-kitchen with a mini-double sink, mini-stove/over microwave ½ dishwasher, and medium-sized fridge-freezer.
The bath-shower and toilet were the best! For some reason, Mom and Dad put in dual shower heads, so maybe they thought I would soon be showering after sex with a partner or something or someone. It was wall-to-wall and floor-to-ceiling black tiles with intermixed navy blue and deep grey sections. It is masculine and cozy, open in the 8ft X 10 ft room. The two shower heads on the sides pointed to the inside along the end of each 10 ft wall, so 8ft apart with a multi-head panel sprayer and waterfalls. Four feet beside it was the open modern toilet, dual 3-foot vanities, and sinks on each side of the middle door, with a counter-to-ceiling mirror above each sink. Across from the toilet (beside the other vanity/sink) was a large composite water-resistant storage locker for towels, toiletries, and whatever I wanted.
Out of the short hallway were closets with most of my clothes as I sleep nude on the pullouts often—another door to the furnace and HVAC room and a walkout basement door to the backyard and pool. Yes, we had a fantastic 20ft X 40ft oval pool. Besides, there is a sauna, shower, and hot-tub cabana outside with a heavily shrubbed and treed private fenced yard, and our house is on a large lot at the end of a very private lane. It was impossible for us to see any neighbors and for them to see us. The pool and cabana were four seasons as Mom and Dad would contract out to erect a winter-rated plexiglass removable sunroom over the entire massive space. It was fantastic to swim all year long. All my male friends and a few girlfriends enjoyed it with me for 12 months of the year.
Back to the basement. Mom and Dad would never come down without calling my cell first; it would have been a dire emergency, so there were no real worries about interruption. I knew from chats with them that they were both also very sexually open and accepting of any of my choices or activities. Currently, they knew I was privately experimenting with anal penetration on myself.
It was an embarrassing talk when they wanted to make sure I knew all about masturbation, love, sex, and reproduction; they even reviewed toys, dildos, and other self-pleasuring aides and ensured I understood male and female anatomy; anal, vaginal, and penial pleasure. They even gave me one of their medical anatomy books to study. They also wanted me to be a doctor, but I was still undecided. Mom even assured me that if there was any pleasure item that I ever wanted before I was 18, to let her know, and she would buy it for me.
After my anal sex with Lisa, I told Mom what had happened. She explained it takes time and patience for anyone’s anus and rectum to relax and open. I asked her to buy me a large dildo bigger than my penis and that I wanted to experiment with anal penetration on myself. Mom brought me up to speed and said I was just like her and Dad. They had many toys that they used on each other anally, and that I should enjoy and embrace the pleasure and orgasm ejaculations from anal.
A few days later, Mom bought me a beautiful Jock 11” colossal dildo with a suction cup base I could plug onto the bath wall and also a metal douching nozzle; she handed me a case of almond oil (0 Cholesterol) lube, not to be used in the vagina or deep in one's penis but was excellent for silicone toys and anal penetration. Mom re-iterated there was no such thing as too much lube when penetrating the anus and to read a link she would email me on safe anal douching and penetration. Talk about the open and accepting parents or fucking what, eh! Yes, we live in Toronto, Canada. So, get the accent right, eh?
Thank God it was a Friday, and I told Matt I was not feeling well. I carefully douched and played with that dildo the entire fucking weekend. It was hours and hours of riding when I finally had my first hands-free ejaculation, finding my prostate at just the right angle. Don’t get me wrong, the dildo was very painful and really fucking hurt going in the first time; I took hours to relax.
By the following day, with no sleep all night, I was pounding down continuously on that fucker for hours, cumming and cumming so beautifully handsfree and powerfully several feet all over. It was a great anal cum fest all weekend long! When I finally came upstairs late Sunday, Mom said I looked relaxed and happy. We all giggled. Dad said to enjoy it carefully and never worry about noise, and if I ever needed help, to call them with 0 embarrassment.
Months later, Matt was over one Friday night for a sleepover. It was about 1 am, and Mom and Dad were well asleep; even if they were up, they were likely fucking themselves up each other's asses with cocks and dildos anyways. As I said, they would never come down unannounced.
I had only seen Matt's penis before in the school shower half hard and was happy that we were both the same size soft, about 5.5 inches, and each of us had a perfect set of big, but not overly big, balls that hung in a well light tan scrotum. It was expected during shower time for all of us to stare and check out each other's equipment. We did so almost with a school group expectation and relaxation that allowed each other to stare and get a look at each other from all angles fully.
Both Matt and I stood at 6 ft 1 inch and weighed within 5 lbs of each other at 165. We were both lean and somewhat sculpted athletic late teen boys. I thought we were both beautiful. I had dark brown hair, green eyes, and a great smile, and I kept my hair in a faded side shave with the wild, cringy mop top. Matt had thick black hair parted in the middle down to his shoulders with the most beautiful blue eyes and teeth. I was very attracted to him but had never made a move. I was still curious, uncertain which way to swing or maybe both. Yes, I jerked off and rode the dildo, often pretending it was him. God, the barrels of cum I blew fantasizing about him – unreal!
Matt and I, girlfriendless at the time, were downloading and watching porn from my laptop connected to the 84” LCD TV in the TBP. Unexpectedly, and by pure accident, the porn turned out to be bi-sexual.
I spoke. “Oh, whoops, I’ll change it.”
Matt replied, “Oh, just leave it. I am cool with it.” So, I did. We watched as I sat in one of the black leather chairs, and he was on the leather couch. I noticed his massive tent in his loose summer board shorts. I, also, was raging, dripping hard and tearing my shorts. He peered over at me, and I grinned back at him as we watched a girl sucking a guy off; that guy was sucking another much younger, scorching Ginger Twinks huge cock, even bigger than ours.
I nervously suggested to Matt, “Hey bro, look at us here. We are both tearing our shorts with boners and wood, so, like, are you cool if we…if we…. Jerk…off together?”
Matt heaved the most enormous sigh, “Oh, Thank God, you suggested it; I am painfully dying here. Yes, I would love to jerk off together, but can we take off all our clothes because I cum a lot, and it tends to go all over the place.”
I replied, “Totally, dude!” We stood up and stripped 100% naked in front of each other and placed our shirts, board shorts, underwear, shoes, and socks on the other sofa bed. As Matt walked past me to do so, his huge raging dripping cock brushed my thigh. I shuddered and squirted a good load of pre-cum as he laughed. He went back down to the couch and me to the chair. Both of us looked at the TV porn and then back to each other's cock as we watched how we stroked. We got into a serious discussion about technique as we stared and giggled, smiled, and looked at each of our cocks that were practically carbon copies at 8.5” long and with excellent thick bases. I had three or four fingers with the thumb on top, and Matt often alternated to a full fist and then back to a few fingers. In a few minutes, we were both about to cum massively. We both pumped and paid no attention to the TV, but only each other staring about 5 ft apart into the eyes of each other and back to our awesome penises.
Matt cried out, “Oh Fuck! I am going to cum, Fuck Evan! Watch me blow, buddy; it is fucking huge! OOOHHHH FFFFFFUUUUCCCKKK YYYYEEEESSSSSS!” Matt did ejaculate tremendously. Several huge, thick white ropes of semen flew almost 3 feet up in the air and landed back down on his chest, thighs, and some on his face and mouth. This was a ridiculous turn-on. It was all I could do not to run over and lick him clean from head to toe.
I yelled, “OH Fuck! Matt! Bro! Watch this, you fucking cum God! I am going to shoot huge and beat you little fucker. OOOOOHHHHHH GGGGGGGOOOODDD FFFFFFFUUUUCCCLKKKKKK I am CCCCCCUUUUMMMMMMIIIINNNNGGGGG!” Thank God my cum ejaculation was even bigger and stronger than Matts. My semen flew up over 4 feet and some over my head and face to the back of the chair, and then several torrents, all over my chest and stomach, landed on my face and open mouth. All I wished was that Matt had his cock deep pounding my ass is all I could fantasize about.
Matt answered, “Holy Fuck, bro! I thought I blew a lot of cum. Holy fucking shit, man. That is like a small ½ cup or some crazy shit, dude! Now what a fucking wet mess we have to clean up.”
I took a chance and said, “I dare you to eat it all up, bro!!”
Matt looked very seriously at me and said, “This is Vegas here, right buddy? We have been besties for 15 years, so we trust each other with our secrets, right?”
I replied, “Matt, buddy, ….I…..I……I slurp and swallow mine up all the time. I enjoy the feeling and taste; it turns me on.” Now, I was nervous about his stone-cold look. Then he laughed and said,
“Fuck Bro! Me too! I think my boy-cum tastes and feels wonderful. I do not know why so many girls gag and almost hurl...so stupid.” We both smiled and watched each other together, at the same time, bringing our tongues to our hands and fingers into our mouths, moaning and slurping our semen up. It was wild as we both watched each other with our fingers and tongues clean the semen off our bodies and the leather furniture. It was so erotic, wild, feral-like; total turn-on surrender among teen boys.
Matt, very nervous and shaking, after 15 minutes of us cum slurping, said, “Ok, I think this is the last of what is eatable; we will have to wipe down the tongue residue with a wet towel or something.”
I replied nervously, shaking, “Yeah, I think this is the last of my loads, too, in my fingers.” Our cocks were still somewhat stiff. We were both staring at each other about 4 feet apart with our final cum on our hands and fingers. The sexual tension was incredible as we were both so scared to say what we wanted next.
Matt said very slowly and nervously, in a quivering voice, “Can we….can we…. Maybe…maybe….ah….you know…like try to….to taste…”
I finished his sentence, “Each other’s cum. Yeah, Matt, I would like that very much. I have always wondered what another boy's semen tastes like.”
Matt answered, “Awesome, bro come give me those sweet cum covered fingers.” We both walked closer to each other. I slowly lifted my fingers to his mouth, and he did the same to my mouth with his lovely cum. We both moaned and groaned in our mutual cum swap, licking our hands and fingers clean. Our cocks were just an inch apart, rock hard like iron, dripping cum again. After we withdrew our fingers from our mouths, we both licked our lips. It was all either of us could do not to suck each other's face right off.
Just when I was going to lock lips with him, he said, “Can we shower together and clean up some of the sticky cum residue.”
I answered, “Yeah, dude, that would be fun!” We walked into the dual shower. I turned on one showerhead, and Matt turned on the other. We both smiled and stared at each other with wonder and lust, mesmerized as we washed our bodies and hard cocks and ass, locking eyes and taking in each other's perfect teen bodies. We were both so nervous that I did not know why. Fuck I learned watching him that I was so in love with him and wanted him so badly I would do anything to make love with him. My mind and soul now reconciled that I was in love with my best friend of over 15 years.
After 20 minutes of each of us watching each other 4 feet apart, Matt spoke.
“Evan, …we are best friends and always will be, no matter what. I am unsure what either of us is thinking right now, but…but… I had a lot of fun doing this with you, and although we have both had girlfriends, I would like us to do more together sometime…like, dude, are you okay with that…like? Do you know what I mean?”
I very shakily responded, “Matt, I know both of us have raging 18-year-old hormones, and I think it would be fun to experiment and explore our sexuality. So, if you mean for us to try full boy-on-boy sex with each other, yes, I would like to experiment with that with you in the coming days, weeks, and months; our little secret for now anyways, ok…is that what you mean?”
Matt beamed from ear to ear, “Yes, Evan! That is precisely what I mean, but not tonight.”
I replied, “No! Not tonight. You know my parents are both doctors, and I will not even get into how open they are about human sexuality, but I promised them that if I started to do anything with boys, I would get on the PREP. Dad said it is just a total fact that when boys begin to experiment with boys, they often will do it with many boys or even in groups, so how about tomorrow we go together down to the sexual health clinic downtown in the gay village at the college and get on the PREP together?”
Matt replied, “Yeah, that is a great idea, even though we both just ate a bit of each other’s cum.” We giggled.
I said, “Well, Lisa, Rachel, and Stephanie said I took their virginity, and as far as I know, they never cheated on me. And I have never fooled around with anyone else, male or female, until with you tonight.”
I have been girlfriendless for about three months now. Over the last few years, Matt had two girlfriends, Jessica and Chloe. I would often let him borrow the basement pad when my mom and dad were at work to also fuck his girlfriends during lunch break or first thing after school. Matt also broke up with them, as he was oversized like me.
Matt smiled and answered, “Jessica and Chloe said the same. I am sure we are both okay. I recall reading that they do blood and urine tests, so yes, let’s go together tomorrow down to the clinic.”
We hugged and held each other with our hard cocks pressed into one another’s stomach dripping a river of semen down our legs. We both wanted to kiss each other wildly but knew once we did that, there was no way we could not have full sex. Sure, we had condoms, but we both wanted to bareback experiment and feel each other's ejaculation up our hot, warm anal tunnels.
Matt said, “I see you have a douching nozzle. Can I hook it up here for this showerhead if I bring mine?”
I responded, “Yes, of course. And if you have any dildoes or toys that you have secretly experimented with, bring those also.”
Matt continued, “Looks like we have been doing the same thing secretly for years, haven’t we?”
I answered, “Mine is the 11” Jock dildo; Mom gifted it to me a while ago after I told her I wanted to experiment with anal penetration. I ride it many times a week to the best cums.”
Matt said, “Oh Fuck, Evan, I can’t believe that you and I have been secretly doing and wanting the same thing with each other for years now. I have the 10” Jock dildo. My older gay brother Jason bought it for me when I was curious years ago, at age 18. He is the only other one who knows I have experimented with anal penetration. I have always had intense attraction feelings for you, Evan; you are so fucking gorgeous!”
I replied, “It has been mutual, Matt, for a decade. We had better try to get some sleep, buddy.” We both nodded with incredible sexual tension; we knew when we finally let loose together that we were going to whitewash this basement with boy-cum.
It was so hard not to suck and fuck the absolute shit out of each other. We both decided it was safest to sleep in different sofa beds as we always had been doing. We both lay there naked, dripping, hard as marble, staring at each other's face and body for hours, not saying a word about 7 feet apart. At the same time, we were fantasizing about each other, and there was no denying it!
Finally, at 3 AM, we both started to pant and moan together, still so far apart. Neither of us touched our penis or anus or each other. Together we moaned and groaned and watched each other’s penis shake, quiver, and dance as we ejaculated and felt our prostates pump deep in our ass in unison. On our sides, facing each other on each of our beds, with our chests, faces, pillows, and mattresses getting covered in our hands-free cum. We giggled and slurped up again what we could of our semen, both staying on our respective sofa beds. Finally, we collapsed, exhausted, and snored away till almost 11 AM.
We got up, threw on our swimsuits, and went to the pool. We could not keep our eyes off each other.
Before getting dressed and leaving, I asked Matt, “Can I hold your hand, and please come with me to my parents' upstairs so I can tell them where we are together? I know I said our secret, but it is their house, and they are super open, supportive, and accepting, so are you cool with that?”
Matt replied, “Yes, dude! Totally! I am sure my parents will want to know also. Don’t forget my older brother is 100% gay, so after we go to the clinic, will you come to my place and do the same for me?
I replied, “Of course, Matt. We both know we can trust our open and supportive families. Our other friends would be fine with it, but I think we will agree until we see where we go and end up with this; for now, let's keep it with family.”
He answered, “Agreed.” We smiled and, in our bulging tight speedos, walked hand in hand into the house to the kitchen, where both Mom and Dad had that post-morning fuck look as they sipped their coffee at our kitchen island.
Dad spoke first, saying, “Morning, Evan and Matt. What is up boys…other than…?” Dad and Mom smirked as we were both half-hard.
I said, “I always promised to keep you both in the loop with my mental, emotional, physical, and sexual health. You know that Matt and I have been best friends forever. We have decided that we want to explore our sexuality more together and did a little safe, fun stuff last night. We are headed downtown on the subway to the sexual health clinic to get on the PREP and any other therapies they suggest, blood, urine, and whatever else we have to do. We will be engaging in sex together downstairs in the Teen-Boy-Pad. Nobody other than you guys, Matt’s parents, and gay brother are to know at this point. We are unsure where we are going with this and where we will end up…so ….so…OK?
Mom replied, “Oh, For Fuck sake, Evan! Really! You have to ask if we are ok!?! Have you not figured out that your father and I are bi-sexual swingers!?!”
I replied, “What! What are you fucking kidding me!” Matt is giggled away to the point of tears.
Dad answered, “No, we are not! I am very much in Love with your mother; she is with me. However, after giving birth to you when you were around 5 or 6 years old, we both needed to spice things up, so we went to a bisexual swinger’s party. We are both on PREP and all the safe therapies and have been since it came out 12 years ago. So, we both love and have sex in groups with both genders and all orientations. We have been dying to open up to you and ensure you were comfortable with it.
Believe us, we are so happy and proud of you two boys. We want you both to enjoy your maturing sex lives, so there is no embarrassment; we have been dying to go nude around the house and pool ourselves, so boys never feel you need to wear any clothes at any time in the home or backyard, ok?
Matt suddenly giggled and dropped his speedo as his 8” hard dripping penis popped out!
I yelled, “Matt! What the fuck, dude!”
Mom clapped and said, “No, Evan. Now, you, also! Off with it. That is the rule! Here, watch!”
Suddenly, Mom and Dad drop their robes and are naked with us. Two parents in their late 30s are in great shape and very attractive; Dad was getting a woody the same size as me. I was feeling out of place with everybody naked except me. I dropped my speedo, and my hard cock shot a small load onto the kitchen island counter. Matt leaned over and slurped it up.
Mom clapped and said, “See, that is beautiful. So, there's no embarrassment, and you two make as much noise 24/7 365. We do not care; we want you both to have safe, enjoyable fun. Never hesitate to come and ask us for help or answers for anything in either of your lives. Sex out in the yard and pool is OK also, just not so loud that the neighbor hears.
Now, to change the subject. Your Father and I leave in less than a week at the end of June this Thursday for a 6-week bi-sexual swinger’s cruise. You can call, email us, or text, but you two boys and whoever else you might have here can do whatever you want, sexually or other.
Party away, but I want 0 drugs! Weed is fine, but you are both still just 18. We have liquor in the house, and we expect that most of it will still be here when we get back in August. Is that clear!?
Most importantly, we want 0 safety issues, especially concerning the pool. Neither of you has your driver's license, and On-Star will place the 2 Cadillac SUVs in the garage on disable, so no joy-riding is possible. Dad & I will transfer you regular funds weekly, but we plan to give you 20 $250 gift cards, and there will be $10K in cash in the safe hidden. You know where, and you have the combination. So that is it. Your father and I are going to go skinny dip now and then fuck our brains out. You boys get dressed, go to the clinic, and get all Prep and vaccines. Then we want you to come back tonight and fuck your brains out and enjoy each other's body. You are both very hot, gorgeous young men.”
Matt said, “Evan told me you were supportive and open, but I never imagined this! Thanks! You guys are fantastic! I promise we will care for the house and property like we own it ourselves!” Mom and Dad nodded and walked out the patio door nude to the pool and yard.
We just finished our final grade 12 exams two days ago, and school was done for us until we planned college and university in the fall. The only thing on my agenda was my afternoon shifts at the store from Tuesday to Thursday.
Walking back down to the basement, I said, “Do not even fucking say it, ok! Yes, my parents are hot and cool!”
Matt laughed, “Well, you said it first, but your mom’s tits are fantastic. I see now where you get your nice big cock from also!”
I sighed and said, “Shut the fuck up, get dressed, and let's get to the clinic.” That is precisely what we did.
We were both so horny, it was unreal. We got to the College Sexual Health Clinic at 2:30 PM. They had an open-door policy, so you did not need to be enrolled to get services. Seeing as it was the end of the school year, It was not busy. Matt & I got in, presented our Health Cards to a pretty young girl named Amanda, and said we wanted to get Prep and vaccines together. There were just two other boys, evidently under 18 years old, ahead of us. They were both major emo-goth types, tall and skinny with black eyeliner, pale faces, and the famous black spiked hair, lots of wristbands, necklaces, and tattoos.
Thirty minutes later, they ran out, smiling away with a bag of stuff. Matt giggled and said, “They will never reach a bed!” I grinned and chuckled. A lady with a white coat called our names. No one else was in the waiting room, so it was a no-brainer. We walked back hand in hand with her.
She said, “Hello Evan and Matt, I am Dr. Mona. Please make yourselves comfortable on the leather couch here. So, what brings you boys in today? I think the chart here says first-time PREP and Vaccines, yes?”
I replied, “Yes, we have been lifelong best friends since kindergarten and have just now, in the last few days, decided that we would like to explore our sexuality with each other.”
Dr. Mona replied, “That is awesome! I wish all the boys would come down to get safely set up before engaging in sex with each other. So many STI’s would be avoided.”
Matt said, “Well, we did some masturbating together and did eat a bit of each other's semen, but we wanted to do so much more, but safely.”
Dr. Mona said, “Well, I am not too worried; it is tough to get anything from just tasting a bit of boy-cum. Now each of you briefly tell me your health and sexual history, including any penial and anal masturbation, and what sex with what other previous partners; Evan, let's start with you as you are a few weeks younger than Matt and both 18 now.”
I answered, “Ok, I have no health conditions I know of, and I am not on any meds. Ah, I have had 3 girlfriends over the past few years and none for over three months now. We had mutual oral sex, and I did vaginal sex with tried anal with them, always with a condom on for vaginal and anal. As far as I can tell, I got nothing from them and gave them nothing. I masturbate daily, sometimes up to 4 or 6 times, and usually at least two or three times, with a large 11” dildo thrusting in my anus and rectum, stimulating my prostate until I ejaculate hands-free. Sometimes I will anally douche, and other times play dirty.” Matt moaned, and Mona and I chuckled.
Mona asked, “And was the sex enjoyable, and you were happy with your erection and ejaculation with your partner and by yourself?”
I answered, “Yes, the sex was ok, and I did cum, but they complained about my size, and I did not always tell them I was about to insert my penis in their anus, so…. anyways, I love my ejaculation when masturbating and enjoy the anal penetration with my large dildo.”
Mona replied, “Oh dear, I won't say much about that girlfriend anal. It sounds like you know better now. Most importantly, when you and Matt engage in sex, there is communication and feedback as to what you are doing to each other and how it feels. Now Matt, how about you?”
Matt replied, “I have no health conditions and am not on any meds. Ah, I have had two girlfriends, noncurrent; the last one ended a few months ago. We had oral sex and Vaginal with Condom. I wanted to try anal with them, but they never allowed it. As far as I know, I am clear of everything and have never had any issues. It's sort of funny, but I also masturbate about 4-6 times a day, and I have a slightly smaller dildo than Evan. I love my ejaculations and find the anal penetration incredibly enjoyable. That prostate cums are fantastic.”
Mona stated, “Ok, well, we will do mouth swabs, blood work, urine tests, and semen analysis all right here, ok. We will have you out of here in about an hour with all you need to go home with and do it all with each other tonight. Now are both of you ok to fully disrobe so I can visually check your genitals, prostates, and anuses.” We both nodded yes. We were not expecting this, but we were getting turned on.
Mona continued, “Do not be worried about getting erections, as I need to see your penises erect and measure all, and it is best for the visual STI check. As far as the semen sample, you boys can either masturbate, or I can massage the semen out of you when I do the prostate check.” We both nodded fine to the prostate.
In seconds, we were both fully nude, raging hard and lubing like there was no tomorrow. Mona put on some gloves and looked at my penis. She pulled out a measuring tape and measured from my pubic bone to the leaking dripping glans slit tip. Then, around the mid-shaft and base. She lifted my penis, this way, and that way, and squeezed and felt my testicles and penis all up and down. Now my pre-cum was dripping. I could hear Matt's heart beating. He was so excited.
Mona turned and typed some numbers on her computer. She said, “Evan, you have an above-average penis at 8.5” long with 6” at the midshaft in circumference and 6.5” at your base; I see no sign of any abnormalities or STIs, and you’re lubricating beautifully. You can get up on the table on your hands and knees while I check Matt’s genitals. I want you to concentrate on breathing and relaxing your anus and rectum for your prostate check and ejaculation. Matt, you cum over here, and let me check out your penis and testicles.” I nearly ran to the table. I was so turned on. There were semen webs all over me and Matt by now. Mona was lovely, but I thought she had a growing bulge in her pants. So?
She lifted and measured Matt’s penis and massaged his testicles as he moaned a bit. Mona went to her computer and typed again.
“Matt, you also have an above-average penis at 8” long. Your mid-shaft is a little thicker at 6.5”, and you get really wide and thick at your base of 7.5” in circumference; Evan, you should love that when he is balls deep in you. I want you both to realize at 18 that it does not matter if you are straight, gay, bi -trans or anything else. Yes, the penis is pleasurable for a biological male, but your primary source of pleasure is the anus, rectum, prostate, and seminal vesicle. The entire male pelvic floor is so full of nerve endings that it will give you boys such incredible orgasms as you have already found from your anal penetration with your dildos. Apart from oral and anal sex and toys, have you boys thought about trying anal fisting or urethral sounding?”
With my hands and knees on the table, I replied, “Well, we have not thought about it or talked, but I am open to trying anything if Matt wants to. I know I would love to try fisting and sounds I have never thought about, but sure if we can do it safely?”
Matt stated excitedly, “I am turned on about the thought of anal fisting. I can’t believe how you can get your entire hand and arm up a boy's anus and how it seems to feel so good to them in the videos.”
Mona said, “You would be surprised, but your anus and rectums, in time and slow relaxed progress, can expand safely on average for all genders globally to over 9 inches in diameter or 28” in circumference, much bigger than a woman's vagina during childbirth, and that is the minimum, the largest officially ever recorded is almost 16 inches in diameter and 38 inches in circumference. Many videos, even educational websites online, are very professional and accurate; a good one is called Fistfy, so check it out. Matt, do you mind if I call my assistant from the front desk? You both are still the only boys here. She is also a certified prostate massage therapist so that you can get up on the table next to Evan, and we will do your prostate massage and ejaculations together at the same time, ok?”
In a quivering voice, Matt said, “Yeah, sure, she looked stunning.” He grinned as he hopped up on the table next to me. Mona typed an interoffice message to the girl. She walked in behind us, seeing our open gaping assholes and hanging balls with our huge dripping rock cocks.
Mona said, “Boys, this is Amanda. Amanda, this cute little brunette here is Evan, and the black-haired sweet boy is Matt. I will do Evan, and you do Matt, okay?” She nodded as if she was going to dust the room so calmly. It was apparent this was a regular team effort they did. Mona placed a large profile metal plate underneath our dripping cocks. Semen was already pooling on the plate. I looked at Matt in his gorgeous blue eyes, and he looked at my green boys. This was so exciting and erotic. Both Mona and Amanda straddle the table behind us. We heard them glove up and open a fresh tube of lube.
Mona said, “Boys, this is water-based, but when you are home, I advise coconut oil, and even crisco is good for significant fisting. Or you can blow a bundle on any of the expensive fisting lubes online or in the sex shops, but almost all of them is a version of synthetic coconut oil and other vegetable grease or almond oil.”
I answered, “I use almond oil for my dildo.”
Matt answered, “And I use coconut oil for my dildo.”
Amanda said in a sweet voice, “That is funny because when I anal fist my man, I combine Crisco, coconut, and almond oil. The mix is super slick and creamy and lasts for hours.”
Mona answered, “Oh, that is a great recipe; now, boys, just relax, your anus; we will not breach with the knuckles; we will leave that to you for later tonight or this week.” Both Matt and I were moaning and enjoying this immensely. Never in all my days did I dream that we would get our assholes worked and prostates massaged side by side at age 18 by two crazy hot ladies, one that possibly had a cock likely bigger than both of us.
Amanda said, “Oh Matt, that is great; I can feel both your sphincters open and relaxed, so I will go in with four fingers and prostate cum ejaculate you while I hold your large penis pointed to the plate; relax, buddy, here we go.” Matt started to moan and groan as he looked deep into my eyes. Mona said something similar to what Amanda had just said, but I was so interested in Matt that I was oblivious to it. This was almost as exciting as our cum last night. We both started to moan and groan crazily like, and in less than a minute, we both exactly together arched and blew multiple loads all over not just the plate but the table; even with Amanda and Mona pointing our cocks down could not control it.
Mona spoke, “Wow, that is fantastic, guys. Many of you, boys with bigger penises, also have such powerful and huge ejaculations. Excellent job, boys! Thanks, Amanda, wonderful as usual. Amanda took the plates and placed them on the counter near some microscopes and spinning medical, scientific shit. We hopped off the table, and the ladies handed us some paper towels to wipe our assholes. We seated again next to each other naked on the red leather sofa.
Mona said, “Amanda, please stay and help with urine, throat swabs, and blood work.”
She answered, “I'm glad to!” with a big smile. She was in her late twenties and very pretty.
Mona came over and poked my inner elbow, withdrew about four vials of blood, and then covered the puncture with a band-aid. Amanda did, Matt. Mona now took a swab off our throats when the blood was spinning in some medical, scientific thingy. She closed the swabs in their separate vials, shook each one, and then did other tests with it. Amanda came over and handed us each a 1-liter plastic container.
She said, “Time to pee, boys.”
I answered, “I feel like I need to piss, but my prostate is so excited, I am sort of clamped off somewhere.”
Amanda said, “Yes, that is just the swollen prostate, and it is normal. Here you all wanted to find out what urethral sounding is all about, so I will lube up 2-foot ¼ inch black silicone sounds and penetrate your penises through the prostate and into your bladder, which usually opens the pipe, and you will have a great piss.” Matt watched as Amanda lubed the tip of my half-hard cock and the full length of the 2-foot black silicone sound.
Amanda said, “Big breath, Evan, and blow it out slowly.” I watched, holding my liter piss bucket, and suddenly, she grabbed my penis and thrust the sound entirely up my penis in a few seconds. It burned and hurt at first, but then the feeling was a new pleasure, and like I was cumming internally without cum.
I cried out, “OOOHHHHH FFFFFFUUUCCCCCCKKKK MMMMMMEEE, GGGGGGOOOODDDDDD!”
She and Mona laughed as she pulled it out quickly, and my piss hit her right in the mouth. She knew that would happen, so I think it was what she wanted. She laughed and lifted my hand and bucket to cover my flowing piss. She licked her face and lips, swallowing drops of my urine. She smiled and said, “Nice!”
Next was Matt. He was raging erect now at this act. She lubed his sound and stroked his cock. He moaned and sighed and whimpered,
“OOOOHHHHHHHH GGGGGGGOOOOODDDDD HHHHHHHOOOOOLLLLYY SSSSHHHHHIIIITTTT!” She quickly again pulled out the sound and, this time, opened her mouth fully, taking almost a ½ cup of Matt's piss down her mouth before she lifted the liter pail to take the rest of his urine.
Mona laughed and said, “She loves the boy piss so much!”
Amanda giggled, “I hope you boys both try taking each other piss in your throats; it is so excellent and erotic. Sorry, I am addicted.” Amand brought our piss pails over to Mona, where she withdrew the drop and did a bunch of medical, scientific shit. Matt & I sat there smiling away.
Mona said, “Amanda, these two boys are clean as a whistle. Please get their PREP, MPOX, HPV, and HEP Vaccines.” Amanda left the room to get the meds, injections, and scripts.
Mona continued, “Ok, boys, as you heard, all good news and green lights across the board. No STI, and it’s pretty obvious your genitals and prostates are perfect. I encourage you not to fear the anal penetrations and to explore, expand and enjoy your sex and orgasms together. It is such a beautiful age to play and have a blast!” Matt and I beamed. It was all I could do not to suck his face clean off. I have never wanted to kiss him so badly. Mona gave us each our shots, and we took our first PREP Pills. We each had 90 days worth and then would have to come for regular blood and urine every three months. Fuck we could hardly wait if this was the regular service!
She said, “Now you will return in two months and then at six months for the shot boosters. We will send text and email reminders, so do not worry. I know you two are committed to each other, but we all know sometimes people and other boys show up out of the blue. Please take your PREP 1 pill daily, and you are cleared for group play with anyone in a week, so if the opportunity presents itself this Friday or after, enjoy and have fun! You also each have a few dozen pills called Doxy Prep. These are in case the day or so after you are worried you just engaged with someone who might have had any other STIs. Take two at once and are cured. Questions?”
I asked, “How important is it to avoid consuming fecal matter when rimming another boy or douching?”
Mona said, “Oh, Boy! Ok! Here is a complimentary bottle of antibiotics designed just for that. However, it is minimally toxic and does have bacteria and parasites that can be harmful and may make you ill if you consume vast amounts of each other’s or your own shit. Vodka nearby can also help reduce the risk, but you boys are not old enough. (She giggled)
That said, after douching and the water running clear with minimal color, it is relatively safe to have it splash in your mouth and even swallow some. Many people find it incredibly arousing and feral animalistic surrender to take water from another’s rectum. Do not be scared to experiment. But do so safely. When the anus and rectum are empty and even lightly washed and douched, there are far fewer bacteria and less harmful bacteria vs. what is even present in your mouths and throats. Amanda will text you boys the link to my favorite sites that answer all these questions accurately. Anything else?”
Matt asked, “So tonight we are cleared to have oral sex, anal sex, pissing, fisting cum eating and swapping?”
Mona smiled ear to ear, “Yes, Matt! You and Evan do it all night long. Anything between the 2 of you for the first week. After that, you're protected with group play, as well.”
Matt smiled, “Come on, Evan, let's get to my place and get my dildo and douche nozzle. My parents won’t see me for months!” We giggled and left after thanking and shaking Mona and Amanda's hands. We took a few buses and got to Matt’s place, a few blocks from my house. He grabbed my hand this time and walked me beside him into his parent's place. It was supper time, and they had just finished BBQing burgers. His parents were at the table with his older gay brother Jason and his boyfriend.
Matt walked in and said, “Mother, Father, and Jay. Evan and I have been the best of friends our entire life so far. We have decided to begin an experimental sexual relationship. We are not deciding what or where we are going or where we will end up. We just got back from the sexual health clinic and got our PREP, all our vaccines, first shots, and backup meds. Evan's parents are going on a cruise for six weeks, and I will be staying there with him 24/7 for that entire time to house-sit and have sex, lots and lots of boy-on-boy sex.”
His mom replied, “Would you boys like some burgers to go, as I am sure you are anxious and teen boy horny as fuck to get it on.”
Matt yelled, “Mom…Fuck!”
She replied, “Yes, you will! … and we wish you both all the best! Matt, it is time. Your father and I have long sensed your attraction to Evan. Yes, you both experimented with girlfriends…great. We have watched the look you two give each other for many years. You are a lovely couple. Now get your dildo, lube, douche kit, and condoms if you need them anymore, and have a blast!
Matt's brother smiled with his boyfriend, and they said, “Go get'em, tiger!”
Matt's Dad smiled and said, “Get your sweet twink asses upstairs and get you stuff that you need for your two-month sex-cation with Evan. Of course, come back here if you need anything. We will never go over to Evans unless you call us. We will send you off with a supper doggie bag; now go!” We ran like we were escaping the trenches up to Matt's bedroom. He grabbed two knapsacks and his hockey bag. I piled in as much summer clothing as I could from his closet and drawers as he grabbed his dildo, douche, condoms, and lubes.
Matt, puzzled, said, “How the fuck did they know I had a dildo and douche nozzle and this other shit?”
I answered, “Who fucking cares? They likely were secretly checking for drugs in our rooms like all parents do. They never cared about the anal sex toys and shit, so you should not either. Let's get going. I have been working a fantasy with you all the way here on the bus.” We ran downstairs, and Matt’s Mom and Dad, with bro and his beau, were there with two large thermal bags; Matt hugged and kissed all of them and me also! Fuck, it was like we were married or something!
As we bolted out the door, his mom yelled, “Have safe fun, sweeties. We love you both!” We yelled back some shit and ran entirely loaded with all this shit like we were in maneuvers in the fucking Marine Corps with full packs or something.
Ten minutes later, we reached my place at the end of our secluded lane. It was about 7 p.m., and the sun would be up for another few hours. Nearing our side door, I heard thumping and moans inside. Mom and Dad's bedroom was at the front of the house, and so was their ensuite bath. I doubted they would come to the main floor for anything in the next few hours. It was clear they were in a significant fuck and dildo fest again. God, they fucked so much; it gave me the challenge to beat them before they are gone next week.
We ran downstairs and dropped Matt’s stuff in the middle of the room. He grabbed his douche nozzle and went to the bath with it and his coconut oil lube. I stripped naked. He came back in and stripped as well. We woofed down the burgers and a liter of water each as our penises pointed up past the edge of the mini-kitchen island countertop, running like a facet of pre-cum.
Matt asked, “So Evan, what is your fantasy, and how did you want to start this?”
I said, “We promise each other no embarrassment, no laughing, and no saying no to each other for anything and everything we want, no matter how crazy and disgusting, as long as it is somewhat safe.”
Matt peered deep into my eyes, took a fantastic breath, and replied, “Yes, Evan!” Our hearts were racing, and we could see our veins popping. We were both so horny and lusting after each other.
I began, “I want us to douche together and watch each other clean our shit out of our bodies until the water is clear and clean, and we triple-check with a squat, balls deep on our dildos suctioned to the shower tile floor facing each other without touching each other. Then nude, we walk outside, no towel or anything, to the pool and skinny dip, swimming around, displaying our huge, hard cocks to each other. We end after about 10 minutes, and we meet near the water jets in the shallow end. I want us to be close with our backs against the pool jets; our thighs are about 6 inches apart. The rest is a surprise, and I will take the lead, and then we will naturally let it unfold as the two of us become lovers for the first time.”
Matt looked at me intensely and said, “Perfect, I am offering my entire body to you. Anything and everything, nothing is forbidden, ok, deal?”
I answered immediately, “Deal!”
We gulped the last of the water and headed to the showers. We regulated the temperature and pressure of our water panels until we saw light sprinkles gently flow from our metal nozzles. Facing each other, we grabbed our lube and fingered our assholes; and lubed the douche. One always had to be careful as the anti-slip tile on the shower could still get slippery with these oil-based lubes all around it. Slowly we peered into each other eyes as we inserted our douche up our rectums. Both of us gasping, feeling our anus, rectum, and colon fill. In 30 seconds, we both nodded to each other, pulled out our douche, and bore down, squirting out a nice few logs and light brown water. Some of it flowed to the drain, and we repeated it. Our cocks were bursting and purple we were so engorged and horny. Semen was running continuously; our second and third water releases had little feces and were mostly all clear. I was not ready to drink his cunt juice tonight, but I was sure it was something we both wanted and soon. We hosed down all our shit to the drain and threw down some lemon-scented anti-bacterial soap, and washed it all down. We walked over to the bath sink, grabbed our respective dildos, and headed back to the shower.
Matt said, “I have a last-minute request, please. Can we place the dildos close enough that we can hold hands as we lower our assholes to them as they penetrate us together, please?”
I answered, “Oh Fuck, Yes!” We did precisely that. We placed our dongs, lubed them up, and faced each other about three feet apart. We held each other’s hands and lowered our hungry holes to our slick monoliths, never losing our locked eyes. To this point in my life, this was the most erotic, sexually exciting thing I had ever done with anyone. When our large dildo heads popped into our first sphincters, we both let out an incredible gasp and moan. Slowly, our steaming holes devoured them to their bases. Although we both knew we had done this hundreds of times by ourselves, it never felt like this; sharing it with another boy was so wild, feral, and surrendering. We held hands and began to ride and ride. We nodded, knowing that was enough or we were going to cum. We pulled off and showed each other our open holes. Both are crystal clear and nothing but oil lube on our dildos. We were ready.
We walked hand in hand, naked and titanium-hard, out to the pool. We walked down the stairs and swam around close to each other. I had skinny dipped before alone with Mom and Dad not around, but this was my first time nude in the pool with another boy also nude. It was not just another boy, but my lifelong best friend forever. We back stroked and showed our huge 8+ inch cocks to each other. In a minute, we both headed to the shallow end. The sun was setting. It was such a romantic, clear, starry night.
As planned, we ended up with our backs against the water jets, our thighs just 6 inches apart. The only thing we had done so far to each other was fed our cum covered fingers down each other's mouths and throats and hug, pressing our dripping cocks into each other guts.
I said, “Matt, thanks for coming to my graduation sleepover.”
He answered, “I am having the best time ever with you, Evan. Are you scared or nervous?” I saw a tear in Matt’s eyes,
I said, “Yes, but I have never been so excited and happy.” Looking at each other, I pressed my thigh and leg against his. When they touched it, it was more than electricity; it felt like a lightning bolt had passed through us. He reached over and rubbed my inner thigh. I reached over and rubbed his. In seconds, our hands were brushing our floating balls and pubic hair. He grabbed my cock, and I caught his. We stroked for just a few seconds as we moaned, sighed, and gasped loudly.
Together the damn burst immediately. We pulled each other face to face with our cocks banging wildly into each other, our mouths open, we finally locked lips, and we both went utterly fucking crazy with teen boy passion. We opened our mouths, sucked and slobbered wildly, sucking each other mouths and tongues, only to pull off and bite each other necks, faces, and nipples. We held each other tightly, wrapped like pythons, yearning for a decade for this moment. Tears were streaming. We were both weeping, shaking, and breathless.
Matt, sniffled with tears and snot, in full body spasm cried out, “Evan, it is more than just lust. I have been in love with you for 15 fucking years. Why were we so scared and in denial.”
I replied, equally shaking with love and emotion, “Me Too. I am so sorry. I was so stupid, I just …Oh God, I have wanted you so bad. I have blown like oil tankers' worth of cum fantasizing about you! I am so in Love with you, Matt!” We locked our open mouths as we sucked our tongues with wild, violent passion as we held each other tummy fucking our cocks into each other. Decades of love, lust, and yearning gave way between us two teen boys. After 20 minutes, we got our emotions together.
I said, “Matthew, it is time to make love to each other.”
