I met Paul in school. We were both social misfits and outsiders. We loved to be in this status even if it meant occasionally being the target of some jock bully. I felt that I had met a kindred spirit.
There was something vaguely feminine about Paul that stirred feelings in me. He had chestnut brown hair that fell down to his shoulders, a round face, and a pair big brown eyes. He was quite slight and pale, but possessed an exceptionally large penis, which I stole quick , nervous glimpses at during gymn class as we showered. He was teased abot this particular attribute, but he dismissed it as jealousy.
Paul's cock became a primary focus point of my sexual fantasies.
I was at that time in a strange grey area sexually speaking as my fantasies shift wildly between male and female---sometimes in the masturbatorial frenzy. I had many crushes but too paralyzed with fear to ever act on them.
One day Paul invited me over to his house and introduced me to his s****r Alyssa. Alyssa went to a Catholic girl's school and the first time I saw her she was dressed in her uniform--white collar shirt, plaid skirt, white knee-high socks. This sight neary made me collapse, especially the skirt which descended about mid thigh. I shook her hand. I must have had some expression on my face that I was u*********s of and she asked if I was all right. I just nodded like the horny mute that I had devolved into at that moment.
She resembled Paul but her hair was shorter in an appealingly tom boyish fashion. Her breasts were smallish but the white shirt that molded round them made them appear bigger. I stole quick glimpses at them, but I was caught and I went cold. It was the impressions of her nipples underneath the fabric that made me take so many stupid chances. She just smiled at me.
They told me that they were born as conjoined twins, but were seperated shortly afterwards. Paul pushed his pants down round his knees and displayed the the four-inch long scar on his left thigh. Alyssa follwed her b*****r's lead and showed off her corresponding scar on her smooth pale right thigh. I think they knew what they were doing to me. She held up her skirt enough for me to see a great quantity of her white panties. The scar disappeared under the elastic leg band.
Even in my naive condition at the time I felt that there was something very strange about Paul and Alyssa that went beyond the fact that they were fused at the hip at birth. I had no frame of reference to consult so I was left with my suspicions for the time being. I had two main stars in my fantasies now with various teachers and students who made occasional apearances
When school recessed for summer the three of us could now spend more time together. Within those intervening months I had fallen deeply in love with both of them, but they were both very mysterious. I wanted to be whatever they shared.
Slowly I was winning Paul's trust and he began sharing secrets with me which I sat and listened to in rapt silence. The biggest revelation came when he told me that he was bi sexual. Coming from a suburban life that never mentioned such things regarding sex I was unfamiliar with the word and had to ask him to explain it. Paul never made fun of lack of sexual knowledge.
A couple years ago his parents sent him to a psychiatrist with whom he began a relationship. He got a perverse enjoyment that while his mother was out in the waiting room Paul was in the doctor's office getting sweetly fucked on a big soft leather couch. To compound the thrill was the framed photos of the doctor's f****y watching the two of them ponding and writhing. Paul looked over at the dull faces and it made him come. The doctor eagerly licked every drolet of sperm of his lover's body like a mother cat cleaning it's kitten. Paul never felt any deeper feeling and when the therapy stopped the doctor made a couple attempts to continue to see him but Paul showed no interest. He enjoyed the experience and never told a soul until sharing this all with me.
When he finished his story he opened my jeans and extracted me swolled cock. I lay there passively as Paul took my cock into his mouth. One hand gently caressed the shaft as the other kneaded my balls. I glaned down and saw his head bobbing slowly up and down. The warm wet pressure on my cock made my head spin. It was not long before I had an orgasm and flooded my come into his mouth. He gulped down every drop.
For a long while neither one of us spoke. Paul was looked up at me with his hair tousled and partially obscuring his face. He was smiling.
All the while I was very conscious of his finger caressing my asshole. The sensation it provoked was a mixture of pleasure and discomfort. Paul's face remainded an impassive mask.
He managed to push off his pants without much disruption of his current activity. I craned my head to see his cock. Until this moment I had only see it in a flaccid (albeit impressive) state, however now it jutted out from a cloud of soft brown hair, curving slightly upward, the tip partially sheathed beneath a forskin. Paul rubbed it in a slow and gentle motion of his free hand.
I was also fascinated by his scar. I took the bold action and traced my index finger it's length. His eyes lit up when I did this.
"She feels it too," Paul said, shattering the long silence.
"What? Feels what?" I asked very startled by the comment.
"Alyssa feels whatever I feel. Her scar tingles whenever someone touches mine. Conjoined twins share a very special bond that can never be severed."
He must have sensed my nervousness and quietly apologized. He reached into a bedside table drw and produced of lube. He unscrewed the cap and squeezed out a generous portion onto the tips of his fingers, rubbing some on his engorged cock and then some on my asshole.
"Relax, " Paul whispered.
I lay there passively as he knelt on the bed, lifting my legs up and forward toward my chest until I felt the muscles begin to ache. My breathing was becoming more and more labored as panic crept into my mind. Paul repeated his request for me to relax. The word became as chant as I felt the tip of his now insinuating itself into my virginal rectum. As gentle as he attempted to be there was no avoiding the pain that accompanies one's first encounter with anal sex. I silently (or as much as possible) to this situation because I knew it would be my way into Paul's world.
He entered me with calculated motions, pausing periodically while those muscles opened and accepted his cock. He resumed this for a while. His face was turned down at me, smiling sweetly.
I caressed his thigh scar which was by this time quite slick with perspiartion, but provoked a strange and beautiful response from Paul who continued pumping his hips in an ever quickening rhythm.
Once I felt his his pubic hair bristling againt my ass cheeks I knew he was completely in. The ache in my legs faded and became accostomed to the position.
Paul now began to truly fuck me. I loved watching the myriad of expressions that twisted his face. The apelike barking sound coming from my lover grew steadily in pitch as he rapidly approached his own orgasm.
I felt his cock hastily torn from my anal cavity and watched as he frantically pumped the thick shaft until at least a half dozen strong jets of sperm erupted from the tip and splashed over my chest and stomach.
This was my baptizism.
The summer vacation wore on.
One afternoon Paul, Alyssa, and I snuck a city resivoir to go swimming. I was shocked when they both started stripping off their clothes and stood naked at the edge of the water. It was the first time I had ever seen Alyssa nude. I could help staring at her slim, pale body or the dark triangulation of hair between her legs. Neither seemed at all uncomfortable with the other's nudity. I could never be naked in front of my own s****r. They seemed to actually enjoy it and laughed loudly as they splashed about in the water.
I was somewhat more shy about showing my body in a pubic area and could not relinquish my swimming trunks until they were torn down my legs by Paul and Alyssa swimming just below the surface and refused to return them. I gradually became slightly more comfortable but was still timid about walking about as casually as they did.
Paul and Alyssa took turns climbing up a tree and slowly inching out onto a limb that stretched over the water before leaping in. From my angle I got an eyefull of what was hitherto hidden at the apex of that dark triangle. I swam with a very self conscious erection that could be discovered at any moment. I loved looking at their slim lovely bodies and wanted them both.
After a while we were beginning to tire and sat in a small clearing. Alyssa brought some snacks which we ate on a blanket stretched out on the ground. I was still very conscious of my nakedness, but was never teased about this. I could see that they were very close---closer than me and my own s****r. I envied them they ease of their lifestyle.
"So," Alyssa suddenly said, "Paul tells me you two fucked."
My whole body stiffened. I felt somewhat betrayed that he would share this with his s****r. We had had several moments since that first one over the subsequent weeks, growing steadily in pleaure.
I looked over at Paul sitting nearby.
"Don't worry," Alyssa said, leaning close to me in an attempt to deflate my initial amger. "We have no secrets here. Right, Paul?"
"Well, there is one," said Paul, his smile never fading from his face. I briefly hated him.
"Do you think he's ready to know?" she asked her b*****r.
I looked even harder at Paul. Did he tell her about the weird fantasies I blurted out in moments of uncharacteristic confidence that I was confiding them to someone who was as weird as myself.
"I think he is," Paul said follwing a brief silence.
I sat on the edge of the blaanket and watched Alyssa crawl over to Paul and then take his cock into her mouth. Her head bobbed slowly and his cock gradually stiffened.
Paul smiled over at me and beckoned me to join them.
Alyssa was on all fours, her ass poised up high aand her beautiful pink pussy fully exposed. I was still froze by the scene playing out in front of me. Paul's cock was disappearing into his s****r's mouth. How could she take that entire monster. Her jaws was open to it's fullest and her nose was just touching his pubic curls.
Alyssa began to wiggle her ass side to side in her own gesture to join them. I had never seen the vagina of a live female let alone performed oral sex upon one.
I damned my own timidity, but in a sudden great effort I launched myself forward and buring my face into that sweet pussy. I acted on pure instinct as to what I was supposed to be doing. I kissed and licked her passionately and inhaled the scent that increased as I my loving assault. I became bolder with each passing moment and inserted a finger in and enjoyed the sensation of the muscles clenching it. I inserted another finger, another, until I had the majority of my hand lodged in her cunt. I was still flying blind in a manner of speaking. If she moaned I knew that I was doing right. I swirled my fingers and felt her entire body convulse.
My fingers came into contact with something hard at the apex of her pussy. I began pinching it gently between my thumb and forfinger. When I noticed the response it provoked all my attention remained on this tiny bean. Only later would I be told what I had happily blundered upon.
I have no idea how long this all went on for when Paul turned his gaze up from his s****r and now looked at me with a strange glow on his face.
"You have to fuck her now," he said.
I was in no state of mind of question or fear anything.
I resumed fondling Alyssa's pussy as I took a kneeling position behind her. My free hand held my cock and poised it towards that pink slit. As Paul did when he first fucked me I entered Alyssa slowly, savoring the sensation of my cock being consumed. I watched it gradually sink into her.
Our perspiring bodies slapped loudly as I began pounding her with an increasing sense of confidence. All the while Paul watched this, but would not remain a passive observer for long. He stood and walked behind me, fingering my asshole, using his s****r's vaginal fluids to lube it.
Our combined smacking bodies was deafening.
Paul was barking in his usual manner.
Alyssa was just chanting "fuck...fuck..oh, fuck" over and over.
I was more subdued in my own response and enjoyed listening to my two companions.
When was about to ejaculate and pulled my cock out and watched as my sperm glowed very white in contast to Alyssa's summer tanned back. I milked out very last droplet.
Paul gave a long deep grunt and discharged his own load without withdrawing himself from my rectum. I felt a warm stream of sperm dribble down my inner thigh.
After a much needed rest we jumped into the water and swam until the sun began to sink behind the trees. We dressed and walked home.
Alyssa walked between Paul and I, our hands held warmly in her own.
100% (18/0)
Categories: AnalFirst TimeTaboo
Posted by slappywag64
3 years ago    Views: 886
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2 years ago
that was hot
2 years ago
extremely hot story! Will wait for parts 2 and more.
3 years ago
That was great. I hope you write some more.
3 years ago
That was so very HOT. I hope you continue this story.
3 years ago
wish it was longer
3 years ago
3 years ago
cool story