Late Bloomer Gets Lucky Ch. 11

I was downtown dealing with my driver's license which I had recently lost and while walking out of the building after acquiring my replacement license, I saw Ann. She was dressed nicely in a jacket and skirt. Immediately my mind went to sex and how great it was being with her. I never knew what her job was but I walked behind her at a distance and when she turned into one of the buildings I decided that I would go in.

It wasn't a busy building and it looked like it was a mixture of business tenants which were occupying the location. I couldn't see Ann when I entered so I looked at the directory and saw her name on unit 403 then looked for the stairs and headed up. When I got to the 4th floor I looked for 403 and found it quickly. As I knocked on the door I was nervous and excited and my dick was already swelling, pressing against the inside of my pants.

"Come in." I heard her call and I opened the door. "Hi Kevin." Ann greeted me happily, "What brings you here?"

"I was just getting a replacement for my driver's license and I saw you as I was leaving." I explained. "So this would be a personal visit."

"Oh, well that's nice." she said seemingly unaware that my head was full of lust and my body was encouraging it.

"Are you available for a while?" I asked.

"My next appointment is in an hour." Ann stated.

"That's good then." I said as I walked back to the door and locked it. "That should be enough time."

Ann looked a little confused and a little concerned when I turned back and walked toward her.

"I don't understand. What's going on?" she questioned. I stood right in front of her and put my hands on her shoulders as she just stared at me with an inquisitive and somewhat puzzled expression.

As I pulled her toward me I said "I said that I would let you know when I needed you." and I kissed her mouth.

"Oh no. Not here. Not now!" Ann assertively declared as she tried to back away from me.

I held her and kept her from moving away from me as I told her "Yes, here and right now. I don't need to remind you of the consequences do I Ann?" and I kissed her mouth again as I groped her ass through her skirt. "I just locked your door and you have an hour. That's plenty of time." I assured her as I pulled her skirt up. "You have to Ann because I have the video." I continued.

After just a few seconds she declared "Damn it. Ok just a second, I don't want these clothes wrinkled." and she went to a small adjoining room. I followed her in and she removed each item of clothing and hung it up. There was a smaller desk in the room, a couch and a closet as well as a small bathroom. I was right behind her and right up against her when she was down to her underwear and I pulled off her tiny bikini bottom style panties.

My cock was already fighting to get free as I reached around with one hand and cupped her bald mound. I freed my erect penis with my other hand, just pulling my clothes down to mid thigh and my pole slapped against her lower back. As I bent at my knees, I lowered down and pushed my stiff rod into her ass cheeks and I moved my other hand to paw at her small breasts.

As I stroked at her slit with my fingers it started to get wet and I loved the fact that her body betrayed her wishes. It was a huge turn on for me. I positioned my cock head against her ass hole and just pushed at it gently as I played with her pussy and tits. It was just moments and my cock had deposited slippery lube on her anus so that the contact was extra sensitive. Ann's breathing was deepening and her pussy was wet so I wanted to get my cock inside her. My legs were fatigued and my erection ached so I led her to the small couch that was against the wall.

As I started to lower her onto it she said "Just a moment" and grabbed a folded up blanket then spread it on the couch. I was on her and between her legs as soon as she made contact with the couch, grabbing her ass cheeks and sticking my tongue in her mouth. She was breathing quite heavily and as I moved my hips to steer my aching rod into her pussy, she gasped at each bump that the head of my cock made against her as I prodded her with it. I moved forward and the slippery head bumped her clit and deflected over her mound between us. Again, I pushed forward and the head bumped into her flesh but still too high and deflected up between us once more.

After a few more errant stabs with my pole Ann grabbed it and guided it to her hot entrance and I pushed into her. She moaned in my mouth as I continued to stick my tongue into hers. I pushed my throbbing rod into her a little more after each time I pulled out of her and after 5 or 6 thrusts I was fully buried in her cunt. I stopped thrusting for a moment, just breathing as Ann panted in my ear and my swollen erection twitched and pulsed inside her.

After staying still for about a minute I began stroking in and out of her. Her pussy felt so good and to fuck this woman who I had fantasized about so often was an extremely exciting experience. I felt like I would come right away so I periodically stopped stroking and would try to regain my composure with my cock buried in her. As I was stopped collecting myself after only stroking into her a few times, I put my finger against her ass hole and Ann noticeably gasped as my finger made contact. I held her little hole as I began pulling right out of her cunt and pushing back inside her until I was completely buried in her.

My cock head bumped her pussy lips each time I shoved it back inside her and she panted and held me tightly as I fucked her. "I love your hot cunt Ann." I told her as I drove my fat cock back into her. My finger was now in her tight ass hole as I steadily pulled my pole completely out of her and buried it back into her again.

"Kevin...KEVIN!" Ann gasped urgently just before I felt the tightness of her ass hole pulse on my finger. I pushed my cock deep into her pussy and humped a little pushing my pelvic bone against her. Her pussy was flexing hard on my shaft and my cock head but I held on as she came and I kept bumping her as her strong contractions squeezed my cock. Ann panted and whispered "Oh yes!" repeatedly into my ear as she came down over the crest of her orgasm.

As soon as I realized that her pussy was no longer flexing and squeezing my hard cock, I was happy that I was able to last through her climax and I pulled back and pushed into her again. I felt like it was a great accomplishment that I was able to keep from coming during Ann's orgasm, while her warm, wet cunt squeezed me so tight over and over again.

After a few thrusts, I pulled my erect member from her wet warmth and pulled my finger from her ass, immediately guiding my tool to her pink circle. Ann gasped as the fat head made contact with her anus and as I pushed gently she protested, "No Kevin. Please not there."

"Yes Ann. I need it and you will get used to it." I told her while I painted her asshole with my knob. I pushed against her tiny hole and the head of my cock slid into her tight sphincter as she gasped. I pushed again and her tight hole gripped my shaft as her anus closed over the flared rim of my cock head.

"Oh god!" Ann blurted out as my cock invaded her tightness. My throbbing cock was twitching and pulsing as I pushed further into her hot ass and I attacked Ann's mouth with my lips and tongue. She panted as I sucked at her mouth and continued to push my tingling erection into her ass.

"I want to own this ass Ann." I hissed in her mouth and my jerking cock, which was only half into her, began spilling my seed into her rectum. "Oh fuck!" I grunted as my cock flexed, pulsing strongly as my sperm shot into her ass. Ann was panting and moaning as I continued pushing into her tight ass. My cock pulsed with four strong contractions as I eased back then pushed deeper into her ass as if staking a claim.

Ann just held on and gasped "Oh fuck!" over and over. As the flexing of my rod began to subside, I was nearly balls deep in her rectum and the last of my sperm was being deposited in her depths.

I held still in her for a minute or so while my cock was too sensitive for any more stimulation but I remained fully erect and soon began moving in her again. Ann moaned and kissed me as I began pulling out and pushing back into her tight, but now slippery ass. After thrusting ten times or so with my reviving cock, I pulled right out of her and got down between her legs. I put my mouth on her clit and kissed and sucked at her flesh while fingering her cunt.

It seemed to me that Ann really liked to receive oral but I suspected that she never got any in her marriage. I don't think she ever did anal previously either or sucked cock but I somehow understood how maybe someone might just keep to straight fucking with a pussy that squeezes so hard. It was her husband's loss and definitely to my benefit.

Ann really began to moan and groan louder as I licked and sucked her. I continued kissing, fingering and worshipping her pussy while Ann's breathing and moaning encouraged me and drove me to higher levels of excitement. My cock thobbed and ached as I continued applying sloppy, sucking kisses on her clit, and I heard her moaning increase to another level of intensity when I felt her pussy flex a little on my finger.

"Jesus!" Ann half-yelled, and half-grunted as I stood quickly and guided my throbbing meat to her ass hole again. Pushing my cock inside her tight, pulsing ass and placing a thumb against her clit, I began massaging her pussy with side to side movements as I sunk my member deeper into her hot, spasming tightness. "Oh fuck!" she moaned as her ass flexed hard on my cock. I worked a finger into her pussy while I rubbed her clit with my thumb and her vaginal muscles were squeezing so hard that it was even tight on my finger.

I couldn't hold on through this one and as her rectum pulsed and squeezed my cock intensely, my pole began convulsing and sperm spurted nto her ass again. To be getting off while Ann's orgasm was in full swing was amazing as her muscles squeezed against my flexing penis while it pumped sperm into her heat. Her contractions were just after mine by a fraction of a second and she kept gasping "Oh fuck!" every couple of seconds. Soon the flexing began to weaken and our breathing was heavy as we recovered.

I kissed her neck as I waited for our breathing to slow down and I could feel her heart beating as well as my own. When our breathing was normal again I slowly pulled my slightly softening bone out of her tight hole. I climbed off of her and I went to the bathroom to clean up a bit. After I was finished, Ann went in and she ran the water steady for a few minutes.

When Ann emerged from the bathroom she looked great and made her way to her skirt and jacket to finish dressing. She was a sexy woman and in her underwear she was extra sexy. After she was dressed the clock showed 10 minutes before her meeting. "I'll unlock your door now so that you'll be ready for your appointment." I said and turned the deadbolt.

"Uh...yes, thank you." she responded politely.

"Oh it was my pleasure Ann. All of it was my pleasure." I teased. She didn't join in any playful banter, it seemed like she was getting into her professional mindset. I walked up beside her and looked at the open book on her desk. "These are your appointments." I stated more than asked.

"Yes." Ann responsed curtly. She was so serious. "You should probably leave now shouldn't you?"

"I was going to Ann but I see by your appointment book that you have another hour free after this 45 minute meeting." I lectured, "It's not negotiable so don't even start." Ann stood there pursing her lips and biting her tongue. I continued, "I will just go in here and wait for your meeting to wrap up." and I went back into the smaller room where we had just spent the better part of the last hour.

Before too long there was a knock on the door and Ann greeted and invited her client in. There was some small talk before they got down to business and from what I could glean from the conversation was that Ann was a real estate consultant or a civil engineer or something like that. All I knew for sure was that my semi erection was really anticipation the end of the meeting.

Time seemed so slow and it did seem like the meeting would never end as the minutes clicked past but eventually, the man finished up and discussed booking another meeting just before he left. After he left I walked out into Ann's office and locked the door again. My cock swelled immediately. Ann was taking notes but as soon as she finished and set her pen down, I walked over to her and stood beside her chair.

As Ann looked up at me I ran my hand over her head and stroked her hair. Bending down, I kissed her and put my hand down the front of her blouse. "You had better take these clothes off again." I told her and she got up immediately and went into the small room. I followed her in as she was already removing her clothes and I opened my pants, pulling my underwear down, allowing my erection free to sway back and forth.

I sat on the small couch still covered by the blanket and Ann came over to me in her panties and bra. I patted the couch next to me and she sat down. I immediately put my hand behind her neck and guided her face toward my fully erect penis. The fat head was already wet with pre come and Ann took the big swollen mushroom in her mouth, half sucking it and half kissing it.

I guided her mouth with my hand on her neck and head, urging her to move a little faster on my rod. I could feel the fluid which was constantly seeping out of my pole getting pulsed out of my manhood as her mouth moved back and forth on it. I moved my hand from behind her neck and slid it into her underwear stroking her ass. It was only a minute or so later that I took her mouth off of my throbbing erection and stood up.

I laid Ann down on the couch on her back and pulled her bikinis off. As I spread her legs I could see that her pussy was wet and that really turned me on knowing that she loved the sex even when not liking the circumstances. I guided the head of my cock to her wet cunt and pushed it inside her. "Oh god..." she whispered and I pulled it back out of her. I pressed the head to her pussy lips and painted them up and down as if my rod was a brush then pushed it inside her warm cunt again.

After a few strokes I removed my cock from her every time I pulled back, then pushed it all of the way back in until I was balls deep in her. Ann moaned and gasped constantly while I did this and there was a wet kiss sound each time I pulled it out of her. She definitely loved getting fucked like that. "Oh yes Kevin. Yes." she whispered through her moans and gasps. I reached under her and put my finger against her ass hole, spreading our slippery lube over it before sticking my finger in her tight ring.

I held her ass cheek with my hand, my finger deep in her ass while I plunged my swollen hard cock into her cunt again and again with mechanically precise rhythm. Reaching my free hand up, I pulled at Ann's bra and lifted it, pushing it toward her neck so it freed her small breasts. I ran my palm and fingers over them, feeling the softness of their flesh and the firmness of their nipples. My mouth sucked on hers as she panted and gasped and I felt that I was nearing orgasm.

As much as I wanted to prolong things, when I felt a contraction in Ann's ass while her gasping was at full intensity, I went over the edge. I quickly moved my hand from her tits to grasp her other ass cheek and furiously fucked her cunt as her muscles flexed hard on my swollen probe. "Jesus!" Ann gasped as I violently rammed my pole into her convulsing cunt. I licked and sucked at her mouth while she panted and just when the peak of her orgasm passed, a large stream of sperm shot from my dick deep into her hot pussy.

Another stream shot out just before I pulled my finger from her ass and pulled my twitching cock from her cunt. Swiftly, I moved my jerking rod up to Ann's face and a smaller stream of jism landed on one of her breasts as my erection flexed. I got my cock just about into her mouth before the next small squirt flung from the big head and onto her tongue and her mouth closed on my spasming wand.

"Oh yes Ann." I praised, "that's so good." I told her as her tongue moved over my hard dick while it pulsed and deposited the last few small squirts of my sperm into her mouth.

My dick was a little sore after all of this but it was soothing having Ann suck on it. I held her head with both hands and humped her face as she sucked my softening cock. Eventually I pulled my aching dick from her mouth and started to get dressed. Ann went into the bathroom and cleaned up. When she emerged I was fully dressed and as she began putting her skirt on I moved toward her and put my arm around her shoulders.

"Now that I know where your office is I can drop in to visit." I said casually. Ann shot me a stern look and froze. I leaned down and kissed her mouth then reached for her little tits which were snugly packed into her bra. She was still just staring at me defiantly as I straightened up and she was adjusting her skirt. My aching cock twitched and swelled a little. I moved my hand from cupping her breast outside of her bra to inside her bra.

My cock was aching but it was also swelling again. "Don't just think that you can stop in here any time that you want." Ann complained.

"Ann, you don't get to tell me what I can or can't do." I told her smugly then pulled her toward me, turning her so her back was pressed up against me. One of my arms was wrapped around her waist and my other arm was around her arm with my hand holding her breast which held her arm to her side.

"Listen to me!" she protested, "This is where I work. You can't just walk in here any time."

"I can and I will." I told her and I moved her to the small desk and pushed her torso down on it, bending her at her waist. Lifting her shirt above her hips, this time, I gave her no opportunity to remove it.

"Wait." she said, "Let me take it off..." and I leaned my weight down on her. I pushed my bulge into her ass and I opened the drawer in the desk. There were scissors there so I grabbed them and raised my weight off of her but held my other palm against her back, holding her to the desk. I cut her bra off with the scissors and she hissed "What are you doing?!", then I leaned back and cut her bikini panties off too.

"Stop this right now!" Ann almost scolded but by that time my erection was full size and hard as a rock and my lust was in complete control of my actions. My thighs were against the back of Ann's legs and I held her from getting up with one arm while I quickly unbuttoned and unzipped my jeans before pulling them down. I pushed my hips agaist Ann's ass to keep her from getting off of the desk as I kicked my jeans and underwear off.

While Ann struggled, her bare ass was making contact with my balls a little. It was feeding my adrenaline to have her struggle and I ground my hard cock against her ass. "I'm going to fuck you again Ann." I told her as she wiggled a little and made exasperated grunts.

I pushed my erect rod down to place the end right against her ass hole and she gasped as it made contact. "Kevin. Stop!" Ann begged but I just moved my already leaking cock head slightly and sunk it a few inches into her pussy. "Oh god!" she gasped as I pulled back and pushed it into her cunt again. I drooled saliva from my mouth onto her tight pucked ass hole and rubbed it with my thumb before I pushed it in her rectum. The double penetration froze Ann and I fucked my rod into her cunt hard as she gasped.

Ann stopped struggling as soon as my dick was in her and I wrapped my left arm under her to hold her bare tits. My hand held her right breast and my arm slightly squished her left one while I bucked my hips forward again and again driving my hard pole into her pussy. I reached my other hand under her to hold her pussy and finger her clit while I pounded my engorged penis into her.