Summer's Over, College Starts

This is a continuation of "He was My Boss" Chapters 1 & 2. Reading those will provide background as how my life underwent such drastic change.

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Having had a short but intense education in male/male intimacy during the summer following my high school graduation, I was now leaving home for the first time. Thoroughly sexually confused I would now be going to the big city of Austin and starting my college education at THE University of Texas. I had heard all kind of stories about the "hippies", "free love" and "flower power" existing in Austin. I was feeling excited and scared at the same time, not knowing what to expect and hoping I would make it to graduation. Little did I know just how momentous my first year was going to be nor how much my education would entail.

I had to be on campus August 1 to secure my dorm room, confirm my class schedule and buy books. As I was leaving the Co-Op book store on Guadalupe St., I heard what I thought were fire crackers, I thought that maybe the "hippies" were celebrating something. As I started to cross the street, someone yelled to take cover that someone was shooting from the Tower. I believe that was the very first school shooting ever. I ducked back into the doorway of the bookstore and watched as the now historic events played out.

Shaken, confused and trying to absorb all that had just occurred, I made it to my dorm room wondered if I really needed to attend college.

The next day my new "roomie" showed up. He introduced himself as Jack from Alamo Heights in San Antonio. Jack was close to 6 ft. tall, long blond hair tied into a pony tail, and pink sunglasses. Crap, I thought to myself, I had inherited a "hippie" for a roommate, this was going to be an interesting year. Jack was also an engineering major so we did have some commonality, but our friendship would eventually far surpass just having our majors the same. I soon learned that Jack was smart, really smart and he would be a great study partner.

He also came from an affluent family which gave him plenty of spending money. Plus he had a really cool 1961 Impala Coupe, 409, 2x4's, 4 speed, a dream car as compared to my well used '56 Crown Victoria. But strangely, despite our totally different backgrounds and social status we soon became fast friends.

Jack quickly nabbed a girlfriend, a dark haired Latino beauty from Mc Allen named Marisa. I swear to God she looked like Selma Hayek in every way. I often wondered, in my later life, if they could possibly be related?

As Jack was stalking Marisa, I had met a young lady from El Campo named Helen. She was a blonde, blue eyed tomboy that having grown up on a rice farm gave us much in common. Our rural upbringing provided hours of conversations about crops and animals and country life in general.

It didn't take long before the four of us were best friends. We did most things together and developed a strong four-way bond. As the year progressed, we eased into a nonsexual four-way relationship. Sure, both girls would spend hours at our place but up until mid-term semester break I don't think Jack and Marisa were having sex and I know Helen and I weren't. It was a different time back then, a simpler time with perhaps a little more morality. Girls actually believed virginity was something you took to the alter and believe it or not guys wanted the same.

One evening, just before finals, Jack and I were listening to KLBJ rock when Jack asked if I had ever been high. I said, "Sure, I've had a beer or two."

He laughed and said, "No, dumb ass, have you ever smoked pot?"

I said, "Hell no, I'm not going to jail." (as said, it was a different time)

After he admonished me on my lack of cultural knowledge, he pulled out a joint and convinced me to at least try it. We did and I got stoned for the first time. After a few beers and another joint, I was sitting on the couch and Jack was on the floor, he looked at me and said, "Why do you have a boner?"

Surprised, I didn't know what to say, but secretly I had been thinking about my summer fling with Bob. Jack got on his knees and "walked" over to me and stopped between my spread legs. Without saying a word, he reached up and slowly started rubbing my semi-erect cock through my jeans. I had an immediate flash back of last summer and did absolutely nothing to halt what he was doing.

I immediately wished that he would go further, much further. When I didn't object or show any resistance, Jack proceeded to unbutton and undo my zipper. I sat there in a stoned haze and watched as he slowly pulled my now rock hard cock out of my pants and started stroking it. I leaned further back with eyes closed as he fondled my cock and balls, thinking just how good it felt. He stopped, I opened my eyes just in time to watch as he took me into his mouth. His tongue was doing circles around the head of my penis and I was in heaven, he then took me completely into to his mouth proceed to give me a blow job of monumental proportions.

Just as I was about to cum he stopped and said, "Do me too." I kicked off my pants and slid to the floor next to him. I undid his belt buckle, slid down his zipper and yanked his pants to his knees. His cock popped out, sticking straight up. This was the first time I had seen him naked with an erection and it was a grand erection.

I laid down beside him and started stroking his cock, when he started sucking me again I felt that I must return the favor. I took him full into my mouth, my chin resting on his pubic hair. We were on our sides in the classic 69 position, it was now a contest of "one-upmanship". He would do something and I would copy his move but try to do much better. Soon, I was about to explode as I know he was also, so my devious mind wanted to make him cum first.

I reached under him and started rubbing his anus getting just the reaction I expected. I pushed my finger just inside his outer ring and started a slow in and out movement. He stated pushing his ass onto my finger and I got deeper into his ass. He moaned when I found his prostate and I knew I had him. He came so hard and quick that I didn't have time to take his cock out of my mouth.

Shot after shot of cum was filling my mouth and throat. I had no choice but to swallow. I started to cum and I guess he was in the same position as me because he too swallowed all of my cum as well. We both flopped over on our backs, gasping for air. After a little while, having returned to the living world, we looked at at each other and both said "Wow" at the same time. Jack told me that he had never had a finger in his ass before but that he loved it.

We had another beer and half a joint, gave each other a "man" hug and went to bed. I laid awake for a long time thinking about what had just happened. Was it the pot, the beer or my latent homosexual desire. It must have been the pot because Jack had gone gay too.

The fall semester was over and both Jack and I had done quite well with our grades. We were both maintaining a 3.5+ GPA and the girls had done well also. We had a group date before we parted for the mid-term break. Nothing was ever said about our drunken, pot induced mutual cock sucking.

As I was driving home, I was hoping that it wouldn't be a one time thing.

Christmas came and went as did New Year's eve. I talked several times with Helen over the phone and called Jack, but unknown to me, he and his family had gone to Monterrey Mexico for the holidays. Marisa even called wishing me a Merry Christmas. The holidays were over and it was time to go back to school.

SECOND SEMESTER

Returning to campus, I went to my room only to find that Jack and all his belongings were gone. Oh crap, Jack had bailed, now I'd have to deal with a new roomy. I went to the bathroom to pee and found an envelope taped to the mirror. I'm thinking, "Shit, we had a gay sexual experience and he freaked out and left." I removed the note and read; "GRAB ALL YOUR SHIT AND GET OVER TO 4TH & CONGRESS - DAD RENTED US A HOUSE."

I called my parents and got a blessing to move over to Jack's, not a big problem seeing as how I would not be paying any rent. I loaded up and soon found the house. Jack was unloading stuff, lots of stuff into the small house. It was perfect, two bedrooms with 2 attached baths, a common area, kitchen, dinette with a big porch all across the front. Taking my cloths and stuff to my bedroom, I walked in and ran straight into Jack's mother nearly knocking her down.

I dropped everything in a halfhearted attempt to catch her, the result being that we both fell to the floor. I scrambled up, apologizing and helped her get to her feet. I got my first good look at Jack's mother Sherri. My god, the woman was drop dead gorgeous, almost a Natalie Wood look alike. She confirmed that she was quite alright, introducing herself and offering to show me where everything needed to go. I was smitten. She had on a pair of jeans that highlighted the most perfect ass in the world, and she had boobs that were smallish but standing up proudly, showing what I often considered the "perfect boob". (about a C cup, no bra needed) and she wasn't wearing a bra.

I started getting hard and knew I needed to "adjust" quickly. Turning to look at my bathroom, I attempted to re-arrange my cock when Jack came into the room, saw me shoving my cock into a safe place and grinned. Sherri had returned to the common area and Jack seized the opportunity have a laugh at my expense. He jokingly asked, "Did my Mom get you all worked up."

I punched him in the shoulder, "No" I said. I lied.

Jack just laughed and walked back to his Mom. I was organizing my belongings when Jack and Sherri came into my bedroom to say goodbye. She came up and hugged me and said, "Welcome to the family." Pressing those perfect breasts into my chest she hugged me, my cock was growing and trying to burst through my jeans. I swear I felt her pussy rub my cock, and then a coy little smile and a soft kiss on the corner of my lips.

At that moment i would have done just about anything to prolong the moment. Then, she was gone! Waving as she walked away, she said, "Be sure you come home with Jack sometime." We all walked to the door, saying goodbyes and I watched as she got into her car and drove away. The almost perfect woman in the world was gone, but worst of all she was Jack's MOTHER!

The semester dragged on until spring was in the air. Jack and I had a few M2M moments, only mutual sucking and a tiny bit of butt play, and showering together. Helen and I mostly double dated with Jack and Marisa and did almost everything together. We also started getting more and more casual in our group dynamics, we would all often see the others in various stages of undress. We were all fairly comfortable seeing each other in our underwear and some times a few nude flashes as someone made a late night dash to the kitchen.

Spring had sprung in Austin, still cool enough to need a light jacket at night and warm enough to wear cut-offs during the day. It was hard going to class day after day. Spring break was coming and we decided to all go to South Padre Island for 4 days. Jacks mother had reserved us a suite on the beach, so we loaded Jack's car and headed south.

We found the "Island" and our hotel after a 6 1/2 hours ride of constant foreplay, I know that Jack got at least one blowjob en-route, because I thought we would die in Corpus Christi when Jack shot his load into Marisa's mouth and ran off the road. If I hadn't been sucking Helen's nipples, I would have been paying closer attention and alerted Jack to the impending doom. But all in all, no harm done.

It seems surprises never cease. We found out that the hotel "suite" was really a hotel room with 2 Queen beds, oh well, it was spring break. We did all the mandatory spring break activities like beer drinking, sunbathing, swimming, did I say beer drinking?, and SEX.

The first night we were all horny and high, and sex was going to happen. Each couple tried to stay somewhat discreet while fucking under the covers, but pretty much left little to the imagination. This scenario continued through day 2, and by day 3 we were all fucking in full view of the others. On day 4, Jack suggested we all get into one bed and sleep together. As an alternate plan, I suggested we push the two beds together and create a giant bed.

At first, we all just lounged around talking and flirting. Soon the conversation turned sexual with boat loads of innuendos and lots of touching. Helen and I were lightly making out, me playing with her covered tits and looking over at Jack and Marisa I was slightly surprised to see Marisa topless and Jack enthusiastically trying to get as much breast into his mouth as possible.

I motioned for Helen to look over and suggested she remove her top as well. About 2 seconds later she was also topless and I started to kiss and lick her nipples. Jack and Marisa looked over, smiled and gave a "thumbs up" signal. I figured that this might be a once in a lifetime situation and decided to see just how far this sexy little scenario might go. I unbuttoned Helen's pants, lowered the zipper and started rubbing her pussy. Not 3 minutes later I had her cut-off shorts at her ankles. Her panties were moist and her sexual scent was powerful.

Glancing over at Jack, I saw that he was way ahead of me. Both he and Marisa were now naked and making out like they were both "in heat". Without asking I started to pull Helen's panties down, but she stopped me, I motioned for her to look over at our friends. Her eyes went wide and she started smiling. She removed her hand and raised her ass off the bed to make it easier to remove her last garment. I only had my cut-offs on, but was going commando and it only took a couple of seconds until we were all now totally naked and in heavy foreplay. Jack and I were both extremely hard and the girls were wet, sex was in the air and this was promising to be one hell of a night.

Glancing over again at Jack I saw he was now on his knees fucking Marisa like it might be his very last time to have sex. Helen and I were mesmerized, and we just watched as our two very best friends were putting on a sex show. All of a sudden Helen crawled over to the our friends and started rubbing Marisa's tits. Now I was the one spellbound. Where did THIS come from, Helen liked girls??? I never had a clue that that would have ever been possible, but I'm watching MY girlfriend suck my roomy's girlfriend's tits, and being very enthusiastic about it.

With Helen's ass in the air, I had little choice but to crawl over and rub her pussy, I slipped my finger inside her very wet and warm pussy, with my thumb teasing her asshole when she pushed down hard on my hand. In so doing my very lubricated thumb slipped fully inside her tight little anus. I could feel my fingers with my thumb witch seemed to increase Helen's pleasure. As I was trying to absorb all that was going on, I felt a hand cup my balls and another hand start stroking my rock hard cock.

Jack had my balls and Marisa was slowly jerking me off. So here it was: Helen was tasting Marisa's tits while Jack was fucking her, Jack was fucking Marisa while she played with my cock and he was rolling my balls in his fingers while I was finger fucking Helen's pussy with my thumb in her ass. Perhaps I had died and gone to heaven.

Suddenly, Helen needed and wanted more, she detached herself from my fingers and moved over to sit on Marisa's face. Marisa was more than ready to oblige and raised her head up to lick Helen. Now with Helen occupied with Marisa, I needed something. Detaching my gentiles away from the hands of my two best friends, I moved over behind and below Jack's ass and got an up close view of his cock pumping Maria's sweet little pussy. I couldn't resist the temptation to taste Marisa, so sticking out my tongue, I leaned in and got Jack's cock instead. I did taste Marisa but I also tasted Jack!

I think Jack and Helen had an orgasm together, the only common denominator being Marisa servicing two people. Jack and Helen were both puddles on the bed but Marisa was still very much aroused and she reached out and motioned me to come to her. As I moved forward, she reached out and grabbed my cock, pulling it toward her pussy.

My next move would either end up being a disaster OR pure bliss. Without any consideration, I got my cock just inside Marisa's pussy lips and rapidly shoved my cock balls deep into my best friend's girlfriend. I started fucking Marisa with pure abandon. She wrapped her legs around me and tried to pull me inside her, oh my, this girl really liked to fuck. Marisa stopped, spun around and got on her hands and knees, I took the hint and mounted her doggy style, but I was only partially correct. Marisa wanted me in her ass!

Okay, I can do this. She was tight, her anus was not going to give it up easily. I pushed firmly and finally broke through the outer ring, stopping to let her adjust to my size. I was the same length as Jack but considerably thicker. I slowly slid into Marisa's ass until I felt my balls hit her pussy. I started fucking her ass with gusto, the harder I went, the more she moaned and pushed back against me. I was so turned on I only lasted about 15 strokes before I came harder than I can ever remember, I think I went blind for a few minutes. Marisa and I both collapsed in a semi stroke.

When I could see again, I saw Jack fucking Helen with her legs over his shoulders and his balls slapping her ass. Marisa and I were returning back to life and were watching as our respective lovers were fucking like sex crazed teens, wait; we are all sex crazed teens.

Marisa crawled over on her hands and knees and started sucking Jack's balls and licking his asshole. I was getting hard again seeing as how Marisa was tugging my cock. She motioned me over for what I thought would be another fucking, but she had another idea. She lined my cock up with Jack's anus and tried to push me inside him. Jack suddenly stopped screwing and leaned over until he was laying on Helen pushing his ass up in the air. I slid into Jack's ass and started fucking him while he fucked my girlfriend. Marisa was kissing and licking all over Jack and Helen at any place she could reach while rubbing her clit. I was in sensory overload while blowing my load deep inside Jack's rectum and for the second time having a near black out experience.

We were all totally spent and each coupe reunited for afterglow snuggles, but soon maneuvered into a position where the two girls were face to face with the guys spooned behind them. As I was dozing off I saw that the girls were staring at each other and smiling while playing with each other's boobs. Could life get any better??

The next morning we all took a shower together with a fair amount of playing around. It seems there were no longer any boundaries. We all cleaned the place up a bit, moved the beds back where they belonged and checked out of the hotel. As we left the island, Jack said we would be stopping in San Antonio to eat lunch with his parents and hang out at the pool before heading back to Austin.

The thought of seeing Jack's mother Sherri again certainly caught my interest.

More to come...