Late Bloomer Gets Lucky Ch. 13

It was Thursday after my Saturday night with Jann and I was really needing some action. I didn't know if Jann would be at home on the coming weekend and I felt like I couldn't wait until the weekend, so I just went downtown to Ann's office. The excitement carried over from taking Jann in such a controlling and forceful manner should translate well to my blackmail situation with Ann and her submissive nature with me.

I waited outside her office and after 20 minutes or so a man and a woman emerged from it. I caught the door before it closed and I walked inside. Ann saw me coming in and acted as though things would be just like any other official business meeting even as I walked to her desk and looked at her appointment schedule. "Hello Ann." I said "I need a meeting."

"Hello." Ann replied very dryly.

I saw that she had another appointment scheduled to start in a few minutes but in an hour she was free for 90 minutes so I said "Block off this 90 minute slot for me Ann." Then I leaned in and cupped one of her little tits as I added softly "And no bra or underwear when I come back. Got it?" I looked at her for her answer and she just looked at me, then at the door. "Ok then. See you in an hour." I said cheerfully and walked out of her office. She had another jacket and skirt combination on and I loved that look.

I killed a bit of time walking around town and trying to keep my mind off of Ann. I really just wanted to distract myself until I could get back to her office so I wouldn't have an erection while walking around and so that I wouldn't be vibrating when I walked through her door. After about 50 minutes had passed I headed back and started thinking about what was going to unfold. My dick swelled and my snug jeans weren't helping me keep it under control. By the time that I got to the building, my cock was fully erect so I adjusted it so that it was straight up and walking was not easy.

I got back to Ann's office a few minutes late but now I knew that I had lots of time with her. Ann was at her desk and I greeted her as I walked in. "Did you miss me?" I teased as I checked the small back room.

"I was busy." She replied, sounding serious.

As I walked up to her at her desk I noted that she still had her bra on and I reminded her sternly, "I asked you to do something before I left." She looked like she was going to say something contradictory but she seemed to catch herself then she got up and went into the adjoining room. I smiled and went to her office door and locked it. Ann emerged a couple of minutes later and had had removed her jacket. Her blouse showed her small, unsupported breasts and I could see her nipples through the material. "You look fantastic Ann." I told her as I walked toward her and led her back into the small room.

I led her to the small couch as I unzipped my pants, then pulled them and my underwear down to my ankles and sat down. Ann seemed like she didn't want to look me in the eyes but I noticed that she looked at my erection a couple of times before I reached for her hand and pulled her toward me. I pulled her over my knee and put my right hand flat on her ass.

"Hey...what are you doing?" she asked quietly but sternly. Reaching into her blouse with my left hand, I fondled her breast as I started spanking Ann gently.

"Next time I ask you to do something, I want you to do it." I told her as I spanked her every 2 seconds for a total of 6 slaps. They were very gentle and not on bare skin so it was really just a message and I squeezed her buttock as I kept my hand on her after each slap. I slid my right hand up under her skirt and felt her smooth, soft skin. She took her panties off too! The skirt was a little snug to get a really good feel of her ass cheeks but I moved my hand between her legs and touched her smooth, shaved, bare pussy. Ann gasped as I ran my finger along her slit which was a little moist. "Do you want to take these clothes off now too Ann?" I asked before I helped her up then stood up myself and removed my clothes from around my ankles.

I watched Ann remove the rest of her clothes and hang them up. Then she pulled the blanket out and wrapped it around her. I sat back down and said "Come here." I patted the couch beside me. Ann lowered herself onto the couch with a submissive look on her face and I just looked at my full erection laying against my stomach, then at her and back to my hard cock. Even though I was sure that she'd get the message I put my hand on the back of her neck and pulled her face toward my straining meat. I held my rod so that it pointed straight up and I could see the shiny wetness on the head as it disappeared into Ann's mouth.

"Oh Ann, I've missed you." I whispered as she bobbed on my hard cock. I worked my hand inside the blanket and groped her ass while she blew me. Ann was sucking my aching dick for a couple of minutes before I moved her mouth off of me, laid her on the couch and climbed on top of her. I spread her legs and guided my engorged prick to her warm pussy, gently easing into her cunt, which was nicely lubed by its own natural secretions. Ann was always reluctant but also seemingly always yearning to get fucked.

As I worked my cock into her I kissed her mouth and she enthusiastically kissed me back as I cupped both of her small tits with my hands. Ann was breathing heavily as we kissed, and my breathing was heavy too. As I slowly moved my cock back and forth in her warm pussy I asked her "When was the last time that you had sex?" She seemed like she didn't hear me and our tongues were jousting but I turned away and asked her again right in her ear with some urgency as I moved my hands from her tits down under her to hold her ass. Her arms were around me holding me tightly.

"The last time that you were here." she said abruptly in a whisper, seeming embarrassed.

"What about before that?" I questioned further.

"That time you were at the house." she hurried it out as if to get it over with.

"Really Ann? My god you are so sexy. I don't know how your husband leaves you alone." I told her and she moaned deeply as I sucked her tongue from her mouth then buried my cock in her hot pussy. I pulled back taking my hard pole from her box then brought it up to her mouth and Ann reluctantly took it, closing her lips around it. I ran my fingers through her hair and held the back of her head with my left hand while I stroked her face and jaw with my right hand, pushing my cock gently into her sucking mouth.

When I took my cock out of Ann's mouth she inhaled and panted quite loudly and I pushed my big knob at her lips once more and watched as she took it back into her mouth. I felt her tongue swirl against it and I pulled it out again. She exhaled loudly once more before I covered her little tits with the blanket and moved down between her legs, staring at her clean shaven private areas. I covered her clit with my lips and sucked it with a few loud kisses before moving down her slit, kissing and probing all around her pussy with my tongue.

Ann really seemed to love this kind of attention paid to her pussy and I repeated the process of giving her clit wet, sucking kisses and probing her snatch with a thorough licking. She panted loudly and moaned as I continued, occasionally letting my tongue poke down to touch her ass hole. Ann reacted each time my tongue contacted her tight pink circle and I began poking it at her asshole frequently between kisses that I placed on her clit. After paying her womanly treasures much attention, I stood with my fully engorged penis standing out from my body with a fat, wet, leaking head. Ann was looking at it too with a glazed look in her eyes.

Wasting no time, I moved toward her again, lifting her legs and placing the fat head against her cunt, pushing it inside her. "Oh yes! Fuck me Kevin!" she gasped as I began plunging my hard rod into her. Some wet smacking sounds accompanied each thrust as Ann began groaning through her teeth and I reached under her holding her ass as I fucked my veiny pole into her. As her moaning intensity heightened, I put my middle finger against her ass hole and spread some slippery juice from her pussy on it. "Oh god! Kevin!" Ann gasped as I felt her cunt start to flex.

I buried my cock deep in her then held it still as her cunt squeezed my cock hard over and over. She labored with the contractions gasping loudly and I pushed my finger into her anus slowly fucking her ass with my digit while she came. It was everything I could do to keep from coming while Ann got off. Her panting and groaning coupled with her pussy's strong muscles gripping and releasing my tool while her arms squeezed me so tight was as much as I could take. A couple of her contractions made wet squish sounds as her cunt squeezed my swollen member.

As soon as her flexing ceased, I pulled back and sunk my full length into her hot cunt three times. I slid my finger from her ass then pulled my twitching hard on from her warm hole, quickly moving up to her mouth. Ann's panting mouth was already open but she opened a little wider to accept my lurching meat. "Yes Ann. Yes." I said softly as my sperm pumped into her mouth. Big streams shot into her mouth and she worked to handle it all. "Swallow it." I told her in an encouraging manner as she worked her tongue against my pulsing meat. When my orgasm was over and my cock was finished squirting, I pulled it from Ann's mouth and got between her legs again. Pointing my erection at her cunt, I leaned on it and it sunk in as Ann moaned.

I rested my sensitive dick in Ann's warm pussy and I groped at her tits and ass. Ann was kissing my face and mouth, really responding to all of the stimulation as I slowly started stroking my hard cock into her box. "Oh yes..." Ann gasped "Fuck me Kevin!" That's when I started removing myself completely from her warmth, pausing about an inch away from her then pushing back toward her. The fat head of my rod would bump against her soft pink opening then move right along inside her slippery tunnel and Ann would grunt "Ohhhh..."

"Take that cock Ann." I whispered as I continued to pull right out of her then push all of the way back in again with a wet smack. "You take it." I reinforced and I continued stroking like this while Ann panted and groaned. Working my hands under her ass I gripped her flesh to really pull her toward me as I buried my fuck stick in her warm pussy hole. I moved the middle finger of my right and put it against her ass hole and pushed inside her tight ring.

"Ohhh..." she moaned as every couple of strokes I would take my finger from her ass and rub her anus in circles before pushing back in again. Ann's panting and gasping had risen to a very high intensity and as I felt a contraction on my shaft she gasped in a panic "Oh fuck Kevin!" Again, I pushed my hard shaft in her all of the way to my balls and held it motionless in her. I held still while her muscles squeezed incredibly tightly and released over and over while she wiggled on my cock as if she was speared game and gasped "Ohh!" with each muscular flex of her canal. Her ass was also squeezing my finger with tight pulses and I felt like I was going to let loose but I held until her pussy was no longer flexing and Ann was laying back trying to catch her breath.

I pulled back and stroked hard into her a couple of times then moved my finger from her hot ass hole and slid the head of my swollen, twitching manhood down to Ann's pink button. "Ohhhh..." Ann moaned lazily as I pushed the head inside and immediately started to come, shooting a stream in her hot rectum. I pushed in a little with each spasm of my orgasm and Ann moaned with each push. I continued pumping sperm into her and by the time I finished, I was completely buried in her now well-lubed, hot ass.

I stayed on her as we were catching our breath and my cock began to soften a little. "Are you getting used to getting fucked in the ass Ann?" I asked her. She didn't answer me but kissed me. We continued kissing and I began stroking slowly in her tight ass. Ann moaned with each thrust which sounded like uncomfortable protest but she kept kissing me wantonly. My penis swelled again as I lengthened my stroke, sawing slowly back and forth through her tight anus, I looked up at the time to see that there was plenty of time left and I fell into a steady rhythm in her ass.

Ann was meeting every thrust with a grunt in my mouth. "Ann your ass is so nice." I told her as I continued moving back and forth in her tight tunnel. "Ok, turn over." I ordered as I pulled my slimey cock from her tight sleeve. I helped her turn and when she got to her knees she braced herself with her arms straight, her beautiful bare pussy was on display with her tiny pink dime ass hole just above it. I moved in and placed the fat head of my phallus right against her little wrinkled pink star and pushed.

"Ohhhhh...." Ann groaned as the head pushed right in. I pushed forward about 2 inches and pulled back about inch to a chorus of Ann's groans until I was completely buried in her ass. Reaching under her with one hand, I fondled her little breasts while my other hand cupped her cunt and rubbed her clit.

"Fucking this ass is amazing." I whispered in her ear praising and held my prick buried in her tight, hot depths. I could feel each throb of my erection pulse within her tight sleeve and I was sure that she could too as she breathed slowly and deeply. I withdrew carefully from her after a couple of minutes and took her to the washroom. "Are you okay?" I asked and kissed her mouth.

""I'm okay." she said. I ran the hot water and took the cloth that was there rinsing it in the hot water. I wrung it out and placed it between Ann's legs just giving her a gentle wipe. I rinsed it again and bent her over slightly, cleaning her little butt hole. This would help her feel a little fresher. I then turned my attention to washing my swollen erection off, cupping my hand and running water over it as well as gently wiping it with the cloth. After I was finished I led Ann back out to the couch and sat her down draping the blanket over her shoulders.

I pushed her back slightly and spread her legs, kissing and sucking her clit. Her head was back and her breathing was getting deeper as I placed sucking wet kisses on her clit right down to her fuck hole. My right arm was over her leg and my hand on her little mound with the thumb lightly rubbing her clit. My left hand was under her ass with the thumb right on her ass hole as I strafed her cunt with my lips and tongue. Ann was panting and moaning quite intensely and my cock was aching for contact so I rose from my knees and pulled her up to a seated position, making sure the blanket remained on her shoulders and around her.

I moved my cock toward her face and pushed it down from the base with my left hand. A large drool of pre cum hung off of the shiny wet end as Ann fixed her gaze on it and opened her lips. Her tongue felt so good on the underside of my erect penis and the firm, yet soft ring of her lips around my shaft provided so much relief as she took me in her mouth. She reached up with one hand to hold the base and I held her head and stroked her hair with both hands as she sucked my cock, swirling her tongue around it, holding it with one hand as she kissed it before engulfing it again.

Her breathing was heavy and I could feel her hot exhales from her nose on the base of my rod as well as hear and feel her hot panting when she would take her mouth off of me to kiss up and down my shaft. It was absolutely amazing and her breathing was intensifying dramatically. Looking down, I could see that while Ann was giving me the most incredible head, she was also rubbing her clit furiously. I was getting really close to blowing my load again but I wanted to hold off until she was right on the edge.

Finally her breathing got so intense and she grunted on my cock so I pulled away from her, freeing my hard dick from her mouth. I laid her back, plunging my hard cock into her pussy in one sudden thrust and as I buried myself in her, the muscles of her vagina gripped me in a tight contraction. Furiously I got my hands under her ass and pushed my finger into her asshole. As her muscles relaxed, a stream of semen shot deep into her and she gasped "Jesus!" Then her contraction gripped my meat again. As soon as her muscles relaxed my rod would lurch and throw semen into her.

I just held on with my finger in her ass getting repeatedly squeezed in her rectum and my tool being milked by the tight flexing then relaxing of her cunt, panting while she gasped "OH!" at each contraction. When our orgasms were finished, we just lay there in a heap. My finger was still in her ass and my cock was softening in her pussy while my sperm was flowing out of her. Finally, after our breathing was back to normal, I pulled my finger from her tight butt hole and peeled myself off of her. Ann coughed a little as my weight was significant relative to her size and I apologized "Sorry. I didn't mean to crush you."

"It's ok for short periods of time." she explained.

I helped her up and gave her pussy and ass a nice hot water clean up in the washroom again before she got dressed. A few minutes later when Ann was fully clothed again, there was still 10 minutes before her next appointment. I walked out to her main office and she followed me. I turned and leaned down a bit to hug her and she kissed me on the mouth as I put my arms around her, squeezing her ass gently.

"Okay Ann. I'll be in touch. Hope to see you soon." I said softly and I clearly heard her say 'good bye' but it wasn't really clear what she said after that. It sounded like she said 'I love you.' And I was still deciphering it as I unlocked the door and departed.