My Freshman Year

 After a brief rest, Josh rolled me over on the couch, saying “Rule 2 – Reciprocation”. Suddenly my reality returned, he was going to stick that piece of his man meat into me, after what I just did to him I wasn’t sure that’s what I really wanted done to me, hell I’ve never even put my own finger in my ass. He began by putting his tongue back in my hole as he held my legs up high, with me on my back, he began lapping at my hole like a thirsty dog in a fresh water dish. His warm tongue was heavenly as he swiped from side to side as if cleansing my inner ass cheeks. Eventually with one hand holding my legs up by my under thighs the other up and over my leg grasping my dick, his tongue found my hole as it played and teased it, gradually pressing on the hole and working it like a pro.

Again I’m feeling all kinds of emotion as his hands are pleasuring me one way and his tongue is pleasuring me in ways I never imagined possible before, I still had reluctant anticipation of penetration, but I knew it was inevitable to come tonight, I had to accept that I was going to be breached tonight whether I liked it or not, but he said we’d go slow, well hell, just the other day I was thinking it was too slow, I don’t dare challenge him or refuse him now. His hands moved to my as cheeks, spreading them, allowing what seemed his entire head squeezing between them, as his tongue pressed firmly on my hole, he stopped, he began to speak, ever so softly, “ Don’t worry Buddy, this will be ok, just relax, let me in”, as he pressed harder with his tongue. His soothing style of speech calmed me, but I could still feel myself clenching shut, I had to get over this fear and release myself to him, after all I wanted to, why was I holding back? He began softly speaking again, almost as if he was talking to the hole before him, then out came the tongue again as it gently pressed inside and began a slight penetration, he spent time encircling the outer ring while gently pushing inward, then I felt a finger come from underneath gently pulling down on the opening and his sideways tongue slid in deeper. Those tongue muscles of his were opening me up slowly but surely, as I now had a finger and a tongue inside my hole, I would swear they were all the way in but later as I found out there was a lot more to go.

He began to insert his finger, and then fingers as he backed his face away, and he relaxingly lay on his side continuing to ease my mind with a soft tone voice, assuring me I’d be ok, as his fingers played inside me. I felt both pleasure and pain but which was which, I was so uncomfortable with him touching me there, but I didn’t dare show it. As if he knew, he kept asking if I wanted to go further and I hesitantly said yes simply because I was afraid to stop. He reached for the lube and squirted a ton out, as he rubbed it between his hands, seemingly to possibly warm it up but it was still cold as he rubbed it around the entire area, adding squirts that messily were dripping from my crack onto my lower back and sheets. He pushed the fingers in again this time with much less resistance as the cool liquid touched my burning insides forcing a slight constricting around his digits.

He got up pulling my ass to the edge of the bed had me grabbing my shins with my knees still near my face and he began to slide his dick up and down my crack, fingers still working my hole. Soon he replaced his fingers with his seemingly huge dick head as he pressed ever so gently while still calmly assuring me, it was still ok.

He continued to tease me with dick to ass crack sliding back and forth, each time slowing at my hole and my bitter anticipation of is this the time he stops and he just shoves it in?  all the while his hands began to play with my shrinking dick bringing it back to life again, he looked down on my face only inches from his and all I could see were his reassuring eyes, he didn’t have to tell me a thing, I knew he want going to hurt me, and he sincerely wanted me to have the best time of my life especially as my first. He occasionally reached down with his face giving me the best most satisfying kisses you could imagine.

He began to apply more pressure against my crack spreading my ass cheeks to their maximum as his slippery dick slid up and down, he suddenly stopped and held his dick head at my entrance and then began sliding up and down again, I get the feeling he was enjoying it but my anticipation grew and I think he knew that. I suddenly felt the pain growing as he wasn’t letting up as much anymore and he was holding at my entrance longer and longer and applying more pressure but still not going in, I don’t know if it was that it was me holding him out or if he just couldn’t fit in, either way I felt pain now and I began to panic he said “were going in this time” and his head breached the hole where he stopped and rested, and allowed me to catch my breath, I was breathing like a woman giving birth, and didn’t realize it till he stopped and held still. As soon as I calmed down, he asked “how’s that”? Are you still OK with this? I said “I guess ok, not really sure it’s for me”, he said well were going to try a little further, I blurted out, questioning “You’re not in yet”? He said “No man, I’m sorry but well get there soon, but if you’re still willing, let me go further? I didn’t answer, but my eyes teared up, he brought his face down to mine and licked the tears from my cheek and nose, saying in his soft soothing voice, “were almost there it will be ok again.”.

Not wanting to chicken out I said “Well OK” hesitantly, he then said “Don’t worry it will be worth it I guarantee it”, as he applied more pressure I thought my eyes would pop out of my head and I felt my head was beet red with heat and blood and my eyes were clenched shut. “One last push” he said and in he was in, where we stayed motionless after a tense jerk on my part, for quite a while, as my ass was getting used to him being inside, I began to relax as he let me drop my legs to the side as he rubbed my arms gently and he made me open my eyes. When I did his beautiful face was right there staring right back at me as if he never left that position, he had such a smile on it,  it went from ear to ear and I saw dimples id never seen before, as he looked directly into my soul, and slid his head toward mine for a deep kiss. He said “You did it, I’m fucking all the way into your ass, that beautiful ass I wanted since the first day I met you, now I’m going to start to fuck you, but don’t worry it will be easier and loosen right up pretty darn quick, are you ready”? What the hell at this point I figured, “Sure”. Josh began to slowly pull out only a small amount and then back in, and the strokes gradually got longer and longer, when I found myself rhythm-ing up with him and I grabbed him around his chest as we pumped away feverishly, I raised my legs allowing him in deeper and suddenly that’s all I wanted, was more.

He fucked me every which way to heaven and back, changing the pace and changing it up, he slowed in order to prolong his pleasure and I was feeling every sliding moment inside of me, my dick was rock hard again as the pleasure overtook pain and I was wanting to cum again, I told Josh so, and we rhythmed up again both shooting our loads together simultaneously, me all over myself and the bed sheets, him deep inside me. I have just felt the most amazing feeling of my life. He stayed inside me as his dick shrunk and shriveled away, and as he began to pull out he moaned with sweat and pleasure saying “good god that was so good”, at which point I said Thank you.

He asked how it felt to not be a virgin anymore , and I smiled and acknowledged he was right, I was no longer a virgin and I couldn’t think of a better person to have taken it away from me with strength and class yet so gentle that I was falling in love with this guy, my heart and soul was full of love and my balls and dick were sore, but my ass was more sore than I had ever imagined as josh slid onto the couch laying as he rested his back on the arm and invited me to sit in front of his lap our legs entwined and his limp dick in the small of my back as I rest on his chest and pulled a blanket off the back of the couch and placed it over us. It was about 3 am and it was here we fell asleep.

Oh my gosh what will today bring once we awake,