Warning! The following story is a work of fiction and contains scenes descriptive of sexual encounters and contact between consenting adults. If you are not of legal age to read stories of this nature or you are offended by the subject matter contained herein do not read any further.
Anal Awakening: Friday Wake Up
I awoke early Friday morning feeling the warmth of another body pressing against my backside and the presences of rhythmic breathing. I felt hot breath slowly bathing the area of my left shoulder blade and armpit. There was also something hot and hard prodding below my ass between my legs. As I lazily opened my eyes to a view of Phil's arm draped across my left side. He was tenderly toying with my erect nipple while gently goosing me in the ass with his hard cock, which must've been what woke me up. I gently raised my left leg easing it over Phil's left leg giving his hard cock unfettered access to my asshole. Using my left heal I tried to gently ease him closer to me, all the time pushing my ass back onto his awaiting dick.
Through the fog of first morning light I looked over at the clock radio a few inches away from my face. The digital numbers on the clock face showed a few minutes before six in the morning. If Phil wanted to take me he had at least two hours to complete the job before we were to meet Ian for breakfast. I continued gently grinding my ass back into my best friend's crotch hoping he would get the picture; a picture that I wanted him to fuck me. If he would just whisper the word in my ear the lubricant was only an arms length away.
After a few moments of easy bumping and grinding, without a word Phil easily rolled me over onto my stomach gently resting my backside. As we rolled over he carefully positioned his seven inches of hot hard schlong between the crevice in my buns. He whispered in my ear asking me if his cock felt good in my butt. I cooed back a yes, asking him if he wanted some lube. I heard a faint yes, so I reached into the nightstand drawer retrieving the Astroglide. Phil took the Astroglide as he rose up positioning his knees between my spread legs. He began dribbling some of the lube in my ass crack; the same ass crack he'd been working so vigorously a few minutes earlier. He rubbed the lube up and down the slit, and then dribbled some more lube onto my back too. He then eased forward placing his hard dick into the lubed cleft of my ass.
I felt Phil's well-lubricated seven inches of hard schlong slide into the slit, filling the entire length of the fissure. My ass ached for him to penetrate it as his warm lean muscular body rested gently on my backside; furthermore, I cold feel his thick bush tickling my buns. Finally, I was going to lose my virginity; lose it my best friend who was now also my sister's boyfriend. My mind was a blur and my emotions were running wild thinking about Phil preparing to fuck me; however, I was conflicted, the bad devil on one shoulder told me to do it with a smile while the good devil said no with a frown.
Phil was my sister's boyfriend and my best friend; a friend that I always thought of as a heterosexual who was now dating my sister, how could this be happening? My best friend was getting ready to take my virginity, to fuck me. I could feel Phil moving his body back and forth on my slippery back, letting his hard slick dick slide easily up and down the cleft of my butt cheeks preparing to penetrate my rectal cavity. I hoped he would whisper a warning in my ear before inserting his hard cock into my awaiting asshole; an asshole that quivered with anticipation. Yesterday had been filled with many surprises, but Thursday morning the surprises just kept coming.
I was somewhat surprised that Phil was the aggressor initiating anal sex that morning, but that was the way I truly wanted it. To me, I marked up his early morning behavior to being horny. I listened to him grunt and groan, sighing with pleasure as he slid his seven inches of heaven up and down the slick split in between my buns. He whispered in my ear how smooth and warm my ass felt to him; how he enjoyed the feelings of masturbating in my butt crack. Every once in a while the tip of his dick would graze my super sensitive asshole making me jump, sending shivers of desire throughout my body, to which I responded with pleasurable moans. I quietly asked Phil to warn me before he penetrated my virgin asshole. He replied that he had no intentions of actually penetrating my asshole. He said that we were just engaging in some backdoor frottage, no cornholing.
Backdoor frottage, I'd never heard that term before and had no idea of what it entailed. So, I quietly asked Phil where he'd learned about frottage as he continued sliding his hard dick up and down the crevice in my ass. He told me it was a form of masturbation that he'd heard about during high school. He said that some of the Skater Dudes talked about it and told him that they had done it to sexually satisfy each other. He said that actual anal penetration of another guy's ass was way too gay for him; besides, he didn't want to get any shit on his dick.
Way too gay, did Phil think I was gay? I didn't want Phil leaving for Air Force training thinking his best friend was a gay wad. I humped back in unison with Phil's up and down strokes, trying to make the best of the morning masturbation session we were engaged. I secretly hoped he would miss and stab me in the ass with his sword. Suddenly, I felt Phil's body tense up. He thrust one last powerful push and began shooting blasts of hot cum in my ass crack. He slowed the pace; his movement ceased, and he collapsed totally spent resting on my back. After a few minutes of rest I whispered over my shoulder asking if I could to try it. Phil answered yes, with a tinge of hesitation. We changed positions with each other, but before we lay down again I spread a towel on the bed so as not to get any spooge on the sheets.
I lubed Phil up and began masturbating in his ass crack. I was enjoying the backdoor frottage with Phil, and within a few minutes I exploded in a powerful orgasm, drenching his ass crack with my cum. I lay on top of Phil exhausted and sweating. I looked over at the clock radio, it showed seven-thirty in the morning; that left us about a half hour to shower, get dressed, and meet Ian. I had to remind Phil that we were meeting Ian for breakfast at eight. We got up and both got into the shower together washing each other. Once we dried it was time to shave, brush our teeth, and get dressed. After we dressed and stripped the sheets off the bed I open the windows to air the smell of raw sex from the bedroom. We entered the apartment complex club house a little after eight and found Ian and Lisa already there eating breakfast and chatting.
"Hi guys," I said.
The two responded with greetings. Lisa told Phil she was sorry to hear that he would be leaving next Tuesday. Phil and I went through the buffet getting a couple boxes of cereal each and some fresh fruit. We returned to the table to eat and chat with Ian and Lisa. Once we had all finished eating we got our coffee and sweet rolls and began conversing about plans for the day. I hoped that Ian and Lisa remembered that the party Saturday was a surprise for Phil and not spill the beans. Ian reminded me that he wanted to go by the bike shop down the street. He had decided to purchase the used mountain bike we had looked at the day before. He said that he had checked it out on his uncle's computer online and found it to be a best buy bike.
We finished eating and got ready to leave when Lisa asked if she could join us for the trip to the bike shop. We agreed to include our female friend on the bike buying expedition. We all walked the few blocks to the bike shop arriving as it opened. In a matter of minutes Ian purchased the year old mountain bike for a great deal at $200.00 plus sales tax. The bike had been totally reconditioned ready to ride. We all left the bike shop heading back to my apartment. Ian pushed the bike at first and then got on to ride it. He rode in circles around the three of us walking, beaming proudly about his new purchase. Once we arrived at my apartment he pushed the bike inside and out onto the patio. He locked it to a post and reentered the living room where everyone was sprawled out on the furniture.
In the living room we all were discussing the end of the spring semester and coming events. Lisa was taking one of the same summer school classes as me. I would begin my internship on Tuesday afternoon. Ian was getting English and History out of the way during summer school. And Phil would concentrate his energies on the academic and physical aspects of how to become an airman in the Air Force. There were only a few days before we all started summer school and Phil left for the Air Force, so we decided that those last few days needed to be filled with much partying.
Thus far no one had let the cat out of the bag about the Saturday party that my Mom and sister were throwing for Phil. We decided that Friday night we would have a light party at the apartment complex after we got back from my parent's house. I reminded all that we were going to have KFC for dinner. Suddenly there was a knock at the door. I opened it to find my sister standing there. She looked around as she stepped in, smiled and said, "Did I break up a party or morning ménage a trios?"
"Janie!" I admonished.
"Just kidding," my sister said.
I introduced my sister to Lisa and told her that Lisa would be Ian's date for Saturday, almost letting it slip that we were having a party. Janie looked at me harshly as if to say don't say anything further. No one seemed to catch onto our conversation. Phil made his way over to Janie giving her a kiss on the forehead and saying hello. Janie in return wrapped her arms around Phil's neck pulling him in kissing him full on the lips. I broke the silence asking, "So, what are the plans for the rest of the day?"
Janie responded saying, "I don't know about you guys but I've got a full day planned out for Phil."
My sister pulled Phil towards the door, but before she left I reminded Phil, "Don't forget there's a bachelor party for you here later on tonight after dinner."
Phil and Janie departed leaving the three of us together in the apartment. I asked the burning question, "So, what'll we do for the rest of the day?"
Lisa spoke up and said, "I guess we've been discovered by your sister, so we could just stay here where I'll fuck both you guys for the rest of the day."
Ian and I were caught off guard and in total shock by Lisa's outlandish remark. I'd never heard her talk like that before. She acted completely out of character with that comment.
"Just kidding guys," Lisa said jokingly, "not that I wouldn't enjoy bedding both you handsome hunks."
Of course, everyone chuckled at Lisa's remarks, but I had thought about bedding Lisa a few times since we first met. She was very attractive looking and had a subtle seductiveness about her; however, she was Ian's date for the weekend and I wasn't going to mess with that setup. Lisa asked Ian if he would take her to see Spider Man 3 a local Cineplex. He agreed and the two of them departed the apartment leaving me behind. As the odd man out for the rest of the day I decided to take my mountain bike out for a ride. I needed the exercise as well as some time to think.
As I exited my apartment a little after ten in the morning I was consumed with thoughts about what had transpired earlier between Phil and me. I was oblivious to all pushing my bike towards the street when another of the tenants and fellow students met me in the common area pushing his mountain bike. The tall lean muscular black man interrupted my thoughts asking, "Say Randy, `sup?"
"Just headin out to take a ride."
"Mind if I join?" The young black man asked.
"Naw, in fact, I'd enjoy the company," I said as we gave each other high fives.
Jared had just completed his second year at the university. He was majoring in History. We had never been close friends, just casual acquaintances. We would see each other around campus and the clubhouse occasionally. I didn't remember ever seeing him with a lady hangin on him. He was kind of a loner.
"So, I saw your friend sportin a new mountain bike and saw him with that foxy lookin Lisa in the clubhouse this morning. What gives?"
"Ian is from
"Nice lookin white bread Dude, if he was on the down low I wouldn't eva kick him outa my bed," Jared said.
"What you mean?" I asked my riding partner as we rode along the boulevard.
"You know man; if he wasn't taken by that foxy chick I'd take him home and do him."
"Jared, are you telling me you're gay," I said looking over at Jared a little dismayed by his latest revelation.
"Yeah, been gay since middle school."
I didn't reply to Jared's last comment. I guess I had a lot to learn about people; who was gay and who wasn't. I sure couldn't tell by the way a person appeared externally. The guys that appeared to be gay by external dress and mannerisms many times were straight and vice versus. I sure wouldn't think of Ian or Jared as the gay type, and Phil had always presented as a heterosexual. I secretly wondered how I appeared to those around me. I thought of myself as a straight guy and hopefully I presented that way. But of late I had been questioning my own sexuality.
"So, what's your thing?" Jared asked, "you straight, bi, or gay?"
I looked over at Jared and said, "I really don't know. The only thing I know for sure is I'm a virgin."
"You be kiddin Homey. You ain't never had no sex?" Jared replied with a smile and a laugh.
"Nope, you're probably ridin with the only virgin that goes to our university."
"I doubt that. You let me know if and when you're ever ready to experiment with a very virile African-American," Jared said, "cause you're a dynamite lookin white bread Dude. I'd sure like to get to know better and get into my bed to rock your world."
I looked at Jared and asked, "Do I appear to be gay or straight, Jared?"
"I never thought much about it Randy I don't know you that well, but you looks like a straight Dude to me," Jared replied.
"Thanks," was all I could muster.
"I mean it Randy, if you're confused about your sexuality and want to experiment just lets me knows. It'll be our secret and my pleasure to teach you and no one will ever find out," Jared said seriously.
"Seriously?" I questioned.
"Seriously. We just start off real slow. You know showin off naked in front of each other, maybe jacking each other off a few times. You know, at your pace, whatever," Jared said with a smile, "didn't you ever experiment with your friends when you was younger?"
"Nope never did any of that when I was younger. I guess I'm a late bloomer," I replied, looking at my watch I noticed the time saying, "I think we need to be getting back to the apartment complex."
We turned our bikes around and headed them back towards town. I wasn't lying to Jared. I hadn't started to experiment sexually until a few months ago and it was with Phil. I wanted to go farther with Phil and Ian, but hadn't had the courage to pursue it. I always wanted to do it with Roseanne, but she wanted to remain a virgin until marriage. Today before the bike ride I found myself entertaining thoughts about doing it with Lisa. Now, Jared was propositioning me. I think I just wanted to do it, do it with someone. I wanted to have sex with a person, not my hand. I knew the feelings I'd experienced with Phil and Ian were totally exhilarating, and now Jared was offering to educate me in the ways of gay life. Jared, my fair hued black fellow student and tenant was making an alluringly sexual explicit offer that was almost too good to be true.
That's the end of the story for now, but I leave it open for your interpretations. I need some positive comments to get motivated for future installments. I'll see where things go now with Jared, Randy and Ian. What will become of Phil and Janie's relationship as well as Lisa and Ian? Comments and critics on the story are welcome. If you find any mistakes please feel free to point them out to me. Address all correspondences to Randy at: bn2rumpranger "at" yahoo.com Subject: Anal Awakening
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