Giving My Ass to Jacob

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deleted4783311

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Chapter 1

90 miles left to go until we reach Portland! This trip has taken forever. Three of us are in the car on our way to a week long required training for work. Somehow I always get stuck doing the driving. My boss, Howard, is riding shotgun, and my co-worker Jacob is in the back seat. This is one trip that I was not looking forward to. Other than the open bar, and personal time after the training to explore the city, I had better things to do back at home. Oregon is a beautiful state though, so at least the scenery has been nice to look at along the way. It’s only Monday. Damn. Friday can’t come soon enough.

What I didn’t expect while driving, is to receive a text message from Jacob who is sitting directly behind me in the back seat. Keep in mind…I’m driving and our boss is sitting next to me in the passenger seat. At first I just ignored Jacob’s text message when I saw it come in. That is until Jacob continued nudging the back of my seat to get my attention! I look in rear view mirror and see Jacob mouthing the words, “read it!”

Jacob has quite the sense of humor. He is one hell of a prankster so I’m used to being surprised by his wise-ass antics. Oh here we go…I’m going to open this message and somehow it’s going to embarrass the shit out of me or scare the hell out of my boss. Either way it’s going to make me laugh…probably out loud…guaranteed!! Always does.

I click on Jacob’s message to open it, and it reads “How big is your cock???” Immediately I think “wtf?” and start laughing to myself. I look in the rear view mirror and Jacob winks at me and licks his lips seductively. My boss is oblivious to what is going on. Jacob is a 30-ish year old gay man (total top). I’m 32 and straight. Well, let me back up a little. I’ve only been with women but am very curious. Gay porn and a dildo in my ass are a guilty pleasure of mine. My first time penetrating my ass, I came hard! HARD! Jacob loves to flirt with me at work and watch my face turn red. That’s one of his guilty pleasures.

“Ding.” Another text message comes in…
Jacob: Seriously how big?? Is it tiny or huge?
Me: Lol. You’re stupid. Ok I’ll play along..it’s 8”
Jacob: How thick?
Me: wtf Jacob….ok, 8x6 dumbass!

I continue driving and texting, and by now my boss is getting agitated. “Keep your eyes on the road Tyler. We’re in a damn company car.”

“No shit,” I think to myself. “Thanks for the reminder.” All the while, penis-breath Jacob is in the back seat laughing under his breath at me. I just roll my eyes. We are almost to the hotel, where I can finally get a drink and relax. Jacob and I are good friends, but we do push the line quite a bit. Seriously though, I enjoy the flirting. He gives me a boost I need sometimes. He has warned me several times over the years, “I could blow your mind straight guy!” I laugh it off. Typical Jacob.

We finally reach the hotel and I’m exhausted. Actually this place is a high dollar resort. Absolutely gorgeous and complete with gym, sauna, bar, pool…the works. It’s definitely not a place I could ever afford to pay for on my own. The sun is going down and the Oregon air is damp and cool.

Within another 15 minutes or so, I’m finally in my hotel room. Jacob’s room is a few doors down, and Howard’s room is on another floor. Down in the lobby, I had told Jacob that I would meet him later on in the bar, around 7:30pm or so. Right now though, I’m going to turn on the TV and stand in the shower. This shower is so sexy..see through glass, a huge built in tile seat, and it is divided from the rest of the suite only by frosted glass. I could live here!

After getting cleaned up and relaxing a bit in the suite, I met up with Jacob in the bar. Thankfully Howard was yucking it up in the restaurant with a former colleague. Jacob and I had about enough of his shit anyway and it was only day one of the trip.

Jacob and I sat at a table in the corner of the bar and ordered up a couple of beers. We laughed and joked, and before we knew it, a couple of hours had passed. The music was loud, the cigarette smoke was getting thick, and Jacob and I were getting smashed. Jacob leaned over the table and said to me, “Damn Tyler, your cock is 8” huh? Your cock must be gorgeous!”

“We’ll it is Jake! It’s fat and veiny too,” I said. “I shoot big, creamy loads…10 spurts at a time sometimes!” I suddenly realized I had probably said too much. The alcohol sure as shit broke that barrier down.

“Damn bro!” Jacob said excitedly. “I bet I could make you throw 11 spurts though.” This was classic Jacob. He was always joking around, but this time I felt like giving in to him. I have known him for a long time, and I trusted him. I knew he was up for it too. He had been after me for years, and I played hard to get. Actually, playing hard to get was the easy part. I was nervous as hell. Could I really suck his cock? Would I let him suck mine? Would I let him fuck me?

“Let’s go up to my room.” I said. Jacob grinned from ear to ear, and to the elevator we went.
 
D

deleted4783311

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Chapter 2

Jacob and I got into the elevator. Jacob threw his arm over my shoulder and whispered in my ear, “I want to kiss your nipples and rub my hands over your chest.”

I had never heard another guy tell me this, and I admit it was a huge turn on. The thoughts of another man kissing and caressing my body made my head spin and my dick twitch. I was in good hands with Jacob, so I knew I was in for a great ride…literally most likely. The elevator doors opened, and we quickly made our way to my room. My anticipation was building and the walk to my room seemed to take forever. I slid the key into the slot, the lock clicked open, and just like that…the door shut behind us.

Jacob and I faced each other at the foot of the bed. I unbottoned his pants and let them fall to the floor. His blue boxer briefs seemed to barely contain his erection. I looked down and noticed precum was soaking through his underwear. I slipped my fingers beneath his waist band and freed his raging hard cock. His cock sprang out with force. I admired the sight it! His glans was full, round, rosy pink, and glistening. His dark brown pubes framed his cock perfectly. His shaft was thick and curved slightly upward. The skin of his penis was incredibly warm and velvety to the touch. “Is this what mine feels like too?” I wondered.

Jacob leaned over and kissed my neck while caressing my crotch through my pants. I grasped Jacob’s cock and pumped it up and down gently. My fingers massaged his tip and covered my palm in threads of silver precum. Jacob moaned quietly..almost as if it were a whispered moan. I unbottoned his shirt and tossed it onto the floor. His chest was muscled and beautiful with a dark “happy trail” that ran from his cock to his belly button. His arms were well built and strong. My cock wanted out!!

I laid back onto the bed as Jacob removed my pants and shirt. I leaned my back up against the headboard, and parted my legs. Jacob positioned his head between my knees and pulled my boxer briefs to the side. My loose balls fell free, and he redirected my thick cock to his mouth. His warm, wet tongue slid up my shaft and caressed my frenulum. Precum began to seep from me. Jacob spread my slit open with his tongue. “Wow you taste so sweet,” he said, and removed my underwear. Then in one motion, Jacob took my 8” cock down his throat and buried his face into my light, brown pubes. My engorged cock twitched in his throat. Over the years, I have learned to pump precum out at will. I wanted to give him this little surprise. As his tongue slid over my glans, I pumped a large spurt onto his tongue. He moaned, closed his eyes, and took me down his throat again.

Jacob reached down with his right hand and stroked his throbbing cock as he sucked me off. We were so into each other, and I let him know that I wanted to taste his cock.

Jacob preferred to stand while I knelt down on my hands and knees. I trembled with nervousness as I took his cock into my right hand, and then guided his tip to my lips. I licked the underside of his glans, while taking in the manly smell of his loose balls. Jacob then removed my hands from his cock, and placed his hands on the back of my head. He pumped his hips slowly into my face. “Suck my big cock Tyler,” he groaned. I stroked my hard, wet dick with one hand, and massaged my balls with the other hand. I couldn’t take his full length down my throat yet, but he seemed to enjoy how it felt.

Jacob and I repositioned ourselves on my bed and began a sideways 69. “This is mind blowing!” I thought to myself. Sucking and being sucked at the same time. Is this what Jacob meant by blowing my mind?!! Jacob pumped his cock into my mouth, and I pumped mine into his. He then placed his hand beneath my knee, and raised my leg a little higher into the air. I thought maybe I had done something wrong at first, but quickly figured out he was repositioning me to gain access to my asshole.

Yep there it is! I felt his tongue slide between my cheeks and lick my hole. This is what I have been missing! I removed my mouth from his cock and groaned loadly. I felt my body shutter. Jacob licked my hole while stroking my fat meat. I did not know how much longer I could delay blowing my load…
 
D

deleted4783311

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Chapter 3 (Two parts)

I had wondered what it was like to suck another man’s cock. Admittedly, I was enjoying it…a lot. I loved the feel of him sliding in and out of my mouth. I liked the contour of his massive head, and the warm, sweet taste of the precum that seeped from him. I liked that his cock twitched and swelled repeatedly. Jacob was now steadily rimming my asshole. He spread my cheeks open a little wider, and probed his tongue into my asshole. The dripping from my dick increased to a more constant flow.

Jacob removed his head from between my legs, and sat up on the bed. His cock slipped out from between my lips. I knew what he wanted next, and I nervously rolled over onto my stomach. For the first time, I was about to be on the receiving end of a thick cock and I wasn’t sure how I felt about it. Maybe it just wasn’t going to be my thing, but maybe this guy was going to turn me from being straight! Jacob leaned over and said, “I have been wanting you for so long, are you up to it?” I nodded my head and got on my hands and knees.

Jacob quickly moved in behind me and placed his hands on my ass. My legs were a little too close together for his liking, so he nudged them further apart. I was already breathing hard, anticipating what to expect next. Jacob took a bottle of lube from the nightstand and generously lubed his cock. I then felt the lube drizzle down my ass crack and over my asshole. He caressed my hole and slipped his finger inside. I felt myself clench. He worked his finger in and out. Jacob grasped his cock and rested it against my hole. His warmth was so much different than the cold rubber toys I had experimented with. Instinctively, I was leaning too far forward trying to delay the inevitable a little longer. Jacob held his hard cock against my butthole, and said “Come back onto me.” I did as he asked, and he pressed his cock more firmly against my hole. Fuck! I was too tight. I couldn’t relax enough to let him in.
 
D

deleted4783311

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Chapter 3 - Part 2

Jacob picked up a big pillow from the bed and placed it beneath my stomach. “Here you go buddy, lay flat on the pillow,” he said. I lifted my hips up a little higher and he slid the pillow under me. I laid down flat and noticed that my ass was up high in the air. My aching cock was sandwiched between the pillow and my belly. I turned my head to the side and closed my eyes. I grasped the sheets waiting for what was to come next.

Jacob moved in again behind me and pushed my legs further apart. I felt my ass cheeks spread and expose my hole. He grasped his cock and swirled the head around my hole, and up and down my ass crack. The thick round head easily filled the space between my cheeks. Each time he brushed his cock head over my butthole, I felt it contract. “Fuck this felt so good,” I thought to myself. I loved the feeling of not being in control. I knew I wasn’t going to be able to control the depth or speed once he penetrated me. Jacob dipped his cock head into my hole slightly, and pulled back out. He did this repeatedly. I felt my ass relax and start to invite him in.

Jacob leaned slightly forward and pressed against me popping the tip of his dick into me. I moaned and clenched the sheets tightly. “There you go! “ he said gently. He remained still as I got used to the feeling. His cock felt thick..much thicker than I was expecting. I arched my hips up a little to let him know I was ready for more of his cock. He then pushed his remaining length inside me. My butthole clenched around his shaft and I felt my cock spurt. I knew I hadn’t cum yet, and realized I had shot a gush of precum onto the pillow. I could feel the wetness on my belly.

He began lightly thrusting and I could feel his loose balls against mine. I tried to imagine what it looked like from his view…his cock plunging into my hairy hole and his girth spreading me open. The lube made it so wet and his shaft would be glistening..his pubes mixing with my ass hair. This visualization got me so hot. I could feel my prostate swelling. I was getting sore already, but I wasn’t ready to stop. Jacob moaned as he enjoyed my tight butt. “Do you like this cock in your ass?” he asked. “Fuck yeah Jake,” I moaned out. Jake said, “I’ve been wanting your sweet little ass for so long! I want to fuck you all night. I’m gonna fill that hole with hot cum.” I about came all over myself right then.

I spread my legs a little wider. Jacob’s chest was now pressed against my back and he was grinding me deep. The motion pushed my cock into the pillow with each one of his thrusts.
 

Anonn0027

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Chapter 3 - Part 2

Jacob picked up a big pillow from the bed and placed it beneath my stomach. “Here you go buddy, lay flat on the pillow,” he said. I lifted my hips up a little higher and he slid the pillow under me. I laid down flat and noticed that my ass was up high in the air. My aching cock was sandwiched between the pillow and my belly. I turned my head to the side and closed my eyes. I grasped the sheets waiting for what was to come next.

Jacob moved in again behind me and pushed my legs further apart. I felt my ass cheeks spread and expose my hole. He grasped his cock and swirled the head around my hole, and up and down my ass crack. The thick round head easily filled the space between my cheeks. Each time he brushed his cock head over my butthole, I felt it contract. “Fuck this felt so good,” I thought to myself. I loved the feeling of not being in control. I knew I wasn’t going to be able to control the depth or speed once he penetrated me. Jacob dipped his cock head into my hole slightly, and pulled back out. He did this repeatedly. I felt my ass relax and start to invite him in.

Jacob leaned slightly forward and pressed against me popping the tip of his dick into me. I moaned and clenched the sheets tightly. “There you go! “ he said gently. He remained still as I got used to the feeling. His cock felt thick..much thicker than I was expecting. I arched my hips up a little to let him know I was ready for more of his cock. He then pushed his remaining length inside me. My butthole clenched around his shaft and I felt my cock spurt. I knew I hadn’t cum yet, and realized I had shot a gush of precum onto the pillow. I could feel the wetness on my belly.

He began lightly thrusting and I could feel his loose balls against mine. I tried to imagine what it looked like from his view…his cock plunging into my hairy hole and his girth spreading me open. The lube made it so wet and his shaft would be glistening..his pubes mixing with my ass hair. This visualization got me so hot. I could feel my prostate swelling. I was getting sore already, but I wasn’t ready to stop. Jacob moaned as he enjoyed my tight butt. “Do you like this cock in your ass?” he asked. “Fuck yeah Jake,” I moaned out. Jake said, “I’ve been wanting your sweet little ass for so long! I want to fuck you all night. I’m gonna fill that hole with hot cum.” I about came all over myself right then.

I spread my legs a little wider. Jacob’s chest was now pressed against my back and he was grinding me deep. The motion pushed my cock into the pillow with each one of his thrusts.
Wow love the story and the office romance type deal hehehe. Definitely want to know more!
 
D

deleted4783311

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Chapter 3- Part 2 cont.

As Jacob fucked me from behind, he brought his head next to mine. His heavy breathing near my ear and neck was so hot. His cock continually plunged into my ass. He was getting close to finishing and so was I. I wanted to stroke my cock and get myself off, but Jacob’s full weight was on top of me. My cock was pinned beneath me out of my reach.

Jacob’s penis swelled inside me and he erupted. Wave after wave of his thick cum filled my stretched hole. He braced himself up with his hands and pumped out every last drop. To my surprise, this guy never stopped humping my ass! “Make me cum, Jake!” I shouted out. “I’m so fucking close!” He raised me back up and continued slamming his cock into me. I was now on all fours very close and anxious to blow my load. My cock was pulsing. Jacob reached between my legs and pulled down firmly on my nutsack. The feeling was incredible! It made the skin on my cock extra tight and before I knew it, I shot thick ropes of cum directly out in front of me. His cock still filled my ass as I covered the bed in splatters of white cream. He pulled his dick from me and we both collapsed to the bed, very drunk and exhausted. I must have just passed out soon afterward. I woke up a few hours later with Jacob spooning me. His warm flaccid cock and lightly hairy chest pressed against me. Within a few minutes, I drifted off to sleep again.

Early morning came and I laid there bare assed on my side drifting in and out of sleep. Jacob sensed my restlessness and snuck his finger between my butt cheeks, slowly massaging and probing the hole he plowed the night before. My cock sprung at the sensation, but I did not move. I laid still and enjoyed the massage I was now getting. Pure satisfaction and a hell of a way to be woken up in the morning.

After a long hot shower together where Jacob thoroughly cleaned and sucked my cock, we got dressed and prepared for our morning seminars. Two more days of our trip were left and I pondered what the remaining time would be like.
 

cderekgo

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Chapter 3- Part 2 cont.

As Jacob fucked me from behind, he brought his head next to mine. His heavy breathing near my ear and neck was so hot. His cock continually plunged into my ass. He was getting close to finishing and so was I. I wanted to stroke my cock and get myself off, but Jacob’s full weight was on top of me. My cock was pinned beneath me out of my reach.

Jacob’s penis swelled inside me and he erupted. Wave after wave of his thick cum filled my stretched hole. He braced himself up with his hands and pumped out every last drop. To my surprise, this guy never stopped humping my ass! “Make me cum, Jake!” I shouted out. “I’m so fucking close!” He raised me back up and continued slamming his cock into me. I was now on all fours very close and anxious to blow my load. My cock was pulsing. Jacob reached between my legs and pulled down firmly on my nutsack. The feeling was incredible! It made the skin on my cock extra tight and before I knew it, I shot thick ropes of cum directly out in front of me. His cock still filled my ass as I covered the bed in splatters of white cream. He pulled his dick from me and we both collapsed to the bed, very drunk and exhausted. I must have just passed out soon afterward. I woke up a few hours later with Jacob spooning me. His warm flaccid cock and lightly hairy chest pressed against me. Within a few minutes, I drifted off to sleep again.

Early morning came and I laid there bare assed on my side drifting in and out of sleep. Jacob sensed my restlessness and snuck his finger between my butt cheeks, slowly massaging and probing the hole he plowed the night before. My cock sprung at the sensation, but I did not move. I laid still and enjoyed the massage I was now getting. Pure satisfaction and a hell of a way to be woken up in the morning.

After a long hot shower together where Jacob thoroughly cleaned and sucked my cock, we got dressed and prepared for our morning seminars. Two more days of our trip were left and I pondered what the remaining time would be like.
WOW! Let's hope Jacob jets Tyler on his back, legs high in the air maybe in next 'installment'? Maybe even a flip-flop?
 
D

deleted4783311

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Chapter 4

My co-worker actually fucked my ass last night…that’s all I could think about the next day at our seminar. I was straight the day we arrived here (or so I thought), but now I’m doubting myself. If I want more, I’m pretty sure that means he turned me. Pussy is nice and all, but cock has always been a huge turn on for me. Now I’ve had Jacob inside me, I’ve tasted his dick. I really did want more of it. My decision now was whether or not I was going to go any further with Jacob on this trip. Maybe I need to just take tonight and think this through.

After our day long seminar, I headed to the resort’s gym and put it in a very strenuous workout. Despite the workout music blaring in my ears, my cock leaked through my shorts thinking about last night. I felt that familiar feeling of blue balls creeping in and knew I had to relieve that pressure soon or I was going to be miserable.

I grabbed my gym bag and headed to the locker room. There was only one other guy in there, and he was nearly dressed and almost leaving. I grabbed a towel, dropped my shorts, and headed to the shower. My cock was half erect and my poor congested balls felt full and enormous. My shower cubicle was small and separated by a curtain. I stepped inside and let the steaming hot water run over my body. I lathered my body with soap, of course giving extra attention to my engorged cock.

I could hear a couple of guys enter the locker room. I didn’t care. I pulled the shower curtain about halfway open. I leaned one hand against the shower wall to support myself, and proceeded to massage my balls and jerk myself off under the stream of water. My cock head flared out and swelled with blood with each upward stroke. I propped my leg up against the wall and pushed my middle finger into my asshole.

A naked guy walked by and grinned to himself. His small dick jiggled in front of him. I paid him no mind and pumped my cock with my fist. I could feel my load working it’s way up from my balls. Relief soon!! The first few pearly white drops of cum oozed from my gaping slit. I rubbed it up and down my shaft. I gave my ball sack a firm tug and squirted long ropes onto the shower floor. I tried to muffle my groans but I know I was heard. Hot creamy loads washed down the drain mixed with suds and water. It was instant relief. I stood there for the next few minutes catching my breath, and then wrapped the towel around me and walked back to the locker. All I could think about was getting dressed, going back to the room and taking a little nap.

I got back to my room, undressed down to my underwear, turned the television on, and drifted off to sleep. I slept longer than I had intended and was awoken by the lock on my door clicking open. I had forgot that Jacob and I exchanged room spare room keys the night before. Without saying a word, he climbed into bed with me. I felt his already naked body push up against my cock and chest. I threw my arm around him and pulled him tight up against me. I was half asleep still and drifted off again.

I awoke again to Jacob who was now face to face with me. His thumb was beneath the waist band of my underwear, and he slipped them down over my ass and onto my thighs. He pressed his lips to mine and I helped him get my underwear completely off. We pushed our warm erect cocks together and he slipped his tongue into my mouth. We laid together naked grinding and kissing. He reached down and began stroking our cocks with his right hand. I lowered my head and buried it into his armpit, taking in his smell. I got caught up in the moment and pushed my cock in and out through his hand. Our cocks we’re getting lubed up in his hand. Someone’s cock was seeping. More than likely mine! Fuck this felt hot! It was complete darkness in my room other than the light coming from the television.
 

G Man

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Chapter 4

My co-worker actually fucked my ass last night…that’s all I could think about the next day at our seminar. I was straight the day we arrived here (or so I thought), but now I’m doubting myself. If I want more, I’m pretty sure that means he turned me. Pussy is nice and all, but cock has always been a huge turn on for me. Now I’ve had Jacob inside me, I’ve tasted his dick. I really did want more of it. My decision now was whether or not I was going to go any further with Jacob on this trip. Maybe I need to just take tonight and think this through.

After our day long seminar, I headed to the resort’s gym and put it in a very strenuous workout. Despite the workout music blaring in my ears, my cock leaked through my shorts thinking about last night. I felt that familiar feeling of blue balls creeping in and knew I had to relieve that pressure soon or I was going to be miserable.

I grabbed my gym bag and headed to the locker room. There was only one other guy in there, and he was nearly dressed and almost leaving. I grabbed a towel, dropped my shorts, and headed to the shower. My cock was half erect and my poor congested balls felt full and enormous. My shower cubicle was small and separated by a curtain. I stepped inside and let the steaming hot water run over my body. I lathered my body with soap, of course giving extra attention to my engorged cock.

I could hear a couple of guys enter the locker room. I didn’t care. I pulled the shower curtain about halfway open. I leaned one hand against the shower wall to support myself, and proceeded to massage my balls and jerk myself off under the stream of water. My cock head flared out and swelled with blood with each upward stroke. I propped my leg up against the wall and pushed my middle finger into my asshole.

A naked guy walked by and grinned to himself. His small dick jiggled in front of him. I paid him no mind and pumped my cock with my fist. I could feel my load working it’s way up from my balls. Relief soon!! The first few pearly white drops of cum oozed from my gaping slit. I rubbed it up and down my shaft. I gave my ball sack a firm tug and squirted long ropes onto the shower floor. I tried to muffle my groans but I know I was heard. Hot creamy loads washed down the drain mixed with suds and water. It was instant relief. I stood there for the next few minutes catching my breath, and then wrapped the towel around me and walked back to the locker. All I could think about was getting dressed, going back to the room and taking a little nap.

I got back to my room, undressed down to my underwear, turned the television on, and drifted off to sleep. I slept longer than I had intended and was awoken by the lock on my door clicking open. I had forgot that Jacob and I exchanged room spare room keys the night before. Without saying a word, he climbed into bed with me. I felt his already naked body push up against my cock and chest. I threw my arm around him and pulled him tight up against me. I was half asleep still and drifted off again.

I awoke again to Jacob who was now face to face with me. His thumb was beneath the waist band of my underwear, and he slipped them down over my ass and onto my thighs. He pressed his lips to mine and I helped him get my underwear completely off. We pushed our warm erect cocks together and he slipped his tongue into my mouth. We laid together naked grinding and kissing. He reached down and began stroking our cocks with his right hand. I lowered my head and buried it into his armpit, taking in his smell. I got caught up in the moment and pushed my cock in and out through his hand. Our cocks we’re getting lubed up in his hand. Someone’s cock was seeping. More than likely mine! Fuck this felt hot! It was complete darkness in my room other than the light coming from the television.
Absolutely, you need to let Jacob fill you up again.
 
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