I Stumbled Into A Daily Blowjob

It's the middle of a Monday workday and I'm thinking to myself will anything go as planned today? I arrived on site and caught the concrete crew just in time to correct the shape of drive and sidewalk forms before they were about to be poured. Had I arrived an hour later would have been a major fuckup.

As I'm walking back to my truck to go and grab a quick lunch my cell phone rings. My first thought is "crap" not another issue to deal with and let it ring a few more times until I open the door and get half seated with the door still open.

"Hello, this is Andy" I answered in what must have sounded a little disinterested.

"Hi Andy, this is Jill from the realty office!" She spoke in her typically upbeat professional voice. Jill is an admin at the local realtor office that handles my home listings,

"What's up" I asked.

"Have you got a few minutes to talk? Her voice now had a bit of seriousness.

"Honestly, this isn't the best time to discuss business, can I get back to you later?" I just wanted to go grab a burger and a few minutes to myself before heading to the next jobsite and any issues that might await.

"Well, just let me ask." There was a brief moment of silence. "Were you in anyway serious with your offer Friday?" Uncertainty and worry were evident in her voice.

"I'm not sure what you are asking" Trying my best to understand.

"Oh my, I'm so embarrassed" she said softly. "Please, never mind, my mistake." Her voice had a slight quiver.

"No, no, wait Jill, are you talking about what I think you are?" I'm thinking oh shit, I do know what she's asking.

"Andy, I'm so sorry I called, I'm finding myself getting a little desperate and should have known better. please forgive me." Her voice sounded as if she were holding back tears.

There was a brief silence.

"Listen Jill, I have a lot going on with work this afternoon. Give me a little while and I'll shoot you a text, ok?" And as soon as that came out of my mouth, I'm thinking why I didn't I just accept the apology, be done with it, and move on.

A simple "OK" was her reply.

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Sitting off in a corner of the local fast food Burger joint, my usual "in a hurry" lunch spot, my mind is fixated on that Friday conversation and how to deal with it.

I met Jill 3 years ago at a Derby Party the real estate office held every year. She was there with her daughter that looked to be in her early teens. There were about 60 or so people there and it was nice out for that time of year so about half of us were mingling inside and the other half outside. Everyone was having a good time, drinking, gambling on the races getting a good buzz and enjoying the company all around.

I remember like it was yesterday seeing Jill and her daughter Ashley sort of off to the side, not really mingling so I approached and introduced myself. I estimated Jill to be in her early 30s, maybe 5 or so years younger than myself. As she stood to shake my hand, I found her attractive, and I could clearly see that she had a touch of Asian ancestry in her facial features. Me being 6 ft tall and having to look downward to talk with her allowed me to take in the full view of her petite 5ft 4 frame, sporting somewhere between a C and D cup that perfectly suited her body. Her ruffled, puff sleeved top was unbuttoned low enough to display a peak of her cleavage, I just wished I could see her backside as well. My first impression was a reserved yet friendly mom type, but I couldn't contain the thoughts of what a hot babe she could be in a skimpier outfit. Her daughter Ashley who looked to be maybe 14 didn't speak at all. avoided eye contact, and seemed like she was feeling the awkward, skinny, shy little girl she was, sporting braces and dark frame glasses that looked too large for her face.

We chatted for 15 minutes or so as she asked my relationship with the realtors, which I explained I was a local home builder and Rachel handled my listings. Jill informed me she had been hired 2 weeks previous as the realty office admin/receptionist. She told me she was excited for the opportunity, but only knew a couple of the realtors at the party and felt a little out of place.

Jill leaned into me so her daughter couldn't hear and with a "yikes look" on her face said, "had I known there would be this much drinking and carousing I would have left Ashley at home". I chucked at that, stood and said, "nice to meet you, I suppose I will be seeing you from time to time now." With exchanged smiles I moved back to the party group and noticed it wasn't long before they had left. Later in the day when I asked Rachel why she had left so early, she told me home life with her husband was not good and she probably wanted to get back to avoid any confrontations.

My mind shifted forward to the conversation we had on Friday. Jill was keeping me company in the office board room as Rachel was running late to our meeting, Jill always dressed so nice, a real flare for fashion. We rarely had opportunities like this to talk about personal, rather than business and our conversation ultimately ending up with her sharing her troubles. She had just come out the other side of divorce, they had sold the home per settlement agreement that had zero equity. With little money on hand, she wasn't sure where she and Ashley would be moving to.

Her job at the real estate office was only 30 hours a week, but she needed to keep it for the insurance and other benefits. I attempted to be sympathetic and assuring and suggested things would work out. The upside was she was fairly confident she was about to secure a 2nd part time job at a local hotel where she could work 3 hours a few mornings on weekdays doing odd work cleaning rooms and laundry, before having to show up at the realty office at 11am. Saturdays and Sundays would be all day at the reception desk. The 2 jobs would be pushing a 60-hour week, but they could get by on that.

"Oh my, will you have any time for your daughter?" I asked.

"Without this 2nd job I won't have enough income to rent a place to live. I will do what I have to do until Ashley graduates' high school. That's really as far as I can see right now" she replied.

"Well hell, if you will do all my cleaning, cooking and laundry, you can stay at my house!" I said with a chuckle.

At that moment, Rachel entered the board room in a whirlwind, setting her purse, briefcase and a folder containing the property listing on the boardroom table, the reason I was there to meet her, and abruptly took over the conversation. "Sorry I'm late, but I have all the photos and rough draft of your new listing now and we need to confirm so we can get that baby sold!"

Jill excused herself and left the room to us to take care of business. I never gave it a thought that my little quip would be taken so seriously.

________________________________

Having finished lunch and snaping out of my thoughts, I stared out the window for a few minutes, pulled out my phone and shot Jill a text.

"I think it best we talk in person about this." and pressed send.

Within a minute Jill replied. "Are you sure? You don't have to explain."

"This is not a conversation to text" I replied.

"I'm at work till 5, maybe after? she replied.

"I'll be home by 6, come by any time after. Do you need an address?" I sent the text still wondering why I didn't end this earlier. This involves my realty company relationship, and Jill being Rachel's admin, I will still need to work with her at times, so I need to resolve this asap.

Her reply came back immediately. "Yes, I can do that ;) I have your address on file."

___________________________________

I get home about 5:30 and take a quick shower, throw on a T-shirt and clean pair of jeans. My anxiety is starting to build. I need to be sympathetic, offer what help I can, yet be firm to eliminate any misunderstandings and get this off my plate. Shortly after 6 the doorbell rings, so here goes... I let Jill in, and she is obviously nervous as I offer to take her coat.

"I came straight from work after checking in on Ashley. Hope I'm not too early?"

"Your fine, hope you didn't have trouble finding my place, it is a bit off the highway." I replied.

"Not really, and I love all the space you have away from your neighbors." As she takes her coat off

She hands it to me unveiling an off white and tan scoop neck long sleeved sweater dress that complimented her skin tones beautifully. It hit about mid-thigh sitting atop a pair black of over the knee soft sided boots that that laced all the way up the front leaving about 6 inches of her thighs exposed between boots and dress hem.

Now anytime I have seen Jill at the office, she was always dressed for success, and I'm sure was one of the reasons she was hired as the receptionist. Always soft spoken, upbeat and professional, but most times she was behind her desk where her fashion sense and other assets were not on full display as they were now.

She obviously took great pride in her style and appearance and her perfume was subtle, not a bit overwhelming. The close-knit material of her sweater dress snuggly fit every curve of her body, cleavage perfectly displayed as the material firmly caressed the underside of her breasts and down her flat tummy. What a site to behold, clinging to her ass, separating and defining each cheek as I watched her walk toward living area. WOW, just WOW! This was not the Jill I had envisioned showing up and here I am in a pair of jeans and T-shirt with a sports logo.

"My, what a lovely home Andy, I love the hardwood floors." As she took in her surroundings.

"Thanks, I bought this 3-acre plot about 5 years ago and finally built a house for myself and moved in last summer. Sort of a combination home and display I can let prospective clients' view my work firsthand. I have my office in the basement. Make yourself comfortable in there, can I offer you a drink?" I replied as this horny little guy on my shoulder is whispering in my ear to give in and have this babe move in while I'm trying to resist fucking up my world.

"Just water, thanks" Jill replied from the living area.

After fetching a couple of waters from the fridge I walk into the living area and Jill is sitting just halfway back in her chair, straight up posture, her cleavage is spectacular. Hands on her closed legs as if waiting for an interview.

Her light brown hair is cut just above the shoulders. flipping inward as it falls around her face, parted from the right side with a full sweeping bang that wisped across, covering her forehead, and falling off above her left eye. She kept her makeup light to flatter her eyes with a just a touch of gloss on her lips. Lord help me, she looked awesome in a way I had not really taken notice of before.

I hand her the bottle of water and sit down on the couch across from her and she slides fully back in the chair to get comfortable. When she crosses a leg over the other knee it exposed the top band of her thigh high nylons where a single garter strap is snapped, peeking out the below the hem of her dress. Inwardly I am melting butter. She seems to not realize her dress has hiked up or how badly these exposed hints are affecting me. My cock is starting to stiffen, and I attempt to cover it up. I begin to wonder, is she really unaware how fucking gorgeous her tits are? Do women wear hose with knee high boots? Is she being subtle and purposely displaying herself to me?

"Well Jill, I guess we should talk about that misunderstanding?" My voice a little unsteady.

"I feel I made a fool of myself earlier today. As an afterthought I know you were speaking off the cuff, but I'm at the point of grasping for straws. I apologize for putting you in an awkward position" Jill is looking as if she was about to tear up.

"Don't worry about that Jill, I went through a divorce 10 years ago and understand the stress can get to you. Understand that I'm a 40-year-old bachelor now by design. After I got through my divorce, to recover, I became driven with work and that's how I've managed to have some financial success. I just don't want any sort of relationship at this time, and I have a service that cleans every other week. " I offered up as a first volley.

"I do understand it would be a major intrusion. But to be clear, when I called earlier my expectation would be nothing other than a platonic arrangement. I need time after this divorce as well. Honestly Andy, I have seen how hard you've worked building your business the past 3 years I've known you and find it very admirable. I thought by some slim chance a housekeeper, admin, maid, however defined might have interested you after hearing your comment, but I do understand a live-in with a daughter would be a big change for you." Jill began her pitch before I might shut her down.

"I want to think you have been around me enough over the past few years to know I am an honest, loyal, hardworking person who holds to their word." Jills voice has a slight quiver but needs to deliver the rest of her pitch.

"Let me be as upfront as I possibly can, no BS. I'm broke after paying my attorney, I have to move by this weekend, and I'm hoping to find a place for Ashley and me to stay and call home until she graduates High School. That's 4 1/2 months, and I can make another move then. She's involved in school activities and wants to finish her Senior year here, and I want that for her. I know it's major ask, but what can I offer in exchange for a place for us to settle in for a few months is taking care of all your needs around the house. Laundry, cleaning, your shopping, personal errands, cooking you hot meals every day. Between Ashley and me, this place will stay spotless and organized the way you want. I will purchase all the groceries and I am told I'm a pretty good cook. You set the ground rules any way you deem. Anything else you need help with around here, we will do." Her blue eyes were pleading with me as she spoke.

"Jill, that's a very generous offer, it really is, and I hope you don't think I was implying you were looking for anything more than a platonic situation, I just want to be clear with everything on the table so let me be as upfront as I can... I would have a real concern about your Ex and how he may react if his former wife and daughter were immediately moving in with a man. I certainly don't need an angry Ex I know nothing about causing some real problems." This one was the deal breaker and weighing on me.

"Andy, he is 1000 miles away, in Houston. His brother lives there and directed him to an opening in sales where he works early in our divorce proceedings, and he landed it 2 months ago. He already has a place there and came back once to finalize the remaining details of our settlement. Ashley hasn't heard a word from her dad in almost 3 months, nor have I from him since, that aa...." Jill caught herself and stopped short, as not to interject any negativity. "He has walked away from his daughter and life here and I don't see him ever being around again."

"I see. I'm sure you're ok with that, but I feel for Ashey... that's a shame. But you know I have never had kids for a reason, and don't want to raise kids now and I certainly didn't plan to introduce teen drama into my life at this point. I haven't seen Ashley in years, how old is she now, 17?" I was fudging about my reasoning, I just hadn't dated in several years, it was a hassle developing a relationship, but I really didn't want any high school drama invading my solitude in the evenings.

My cock was getting hard enough to cut diamonds... Jill's cleavage, observing her increasingly desperate demeanor, and I'm realizing this little hot tamale would probably get on her knees and beg to be my live-in servant if that's what it took.

"Ashley turned 18 last October, her dad insisted on holding her back a year after 2nd grade, so she is older than everyone in her class. She's a good girl Andy, She's an A student, mature for her age, loves being in concert band and she's on the track team as well. She is a bit reserved and working hard for scholarships." Jill continued, pushing and pushing.

I am consumed now... Holy shit! I'm in the driver's seat here and it's getting more tempting by the minute, having her hot body on display every evening while she waits on my every need... Even if my need to blow a load was not part of a package deal it would still be pretty awesome for the next 4 months, Like, why the hell not?

"And you don't have the funds to get set up in place? You must have a terrible attorney" I pressed her into a corner.

"You would think, but that's a story for another time. Andy, our house was repossessed, and I have 7 days to remove what I want to keep as well as us from the house. I have maybe $1000 in the bank. I'm serious when I say I'm desperate. With a free place to live I can save until Ashley graduates and get reestablished on my own or I'll have to take on the hotel job as a 2nd and never see her through her Senior year." Jill was laying it out there thick.

I pondered for a minute. "Jill... you are pulling at my heart strings." and she was at that. "But that means you would need to move in immediately, like the next few days."

I paused for a moment, and just looked into her eyes and she was locked into mine trying to read each other.

She was slowly inching her way to the edge of her chair, leaning forward in anticipation. Her arms kept the top of her dress in place, but it caused the bottom of her dress to bunch up, moving further up the bottom side. I'm sure this was the last thing on her mind, waiting for me to announce my next move, but now the full top band of her stockings and garter straps are fully exposed, knee boots, a great cleavage view and in her nervousness her nipples had hardened and become obvious, pushing against the knit material.

My cock is just aching for relief. "Tell you what, and I'm not making any commitment, but let me sleep on it. Bring Ashely with you tomorrow after work. I want to meet and talk with her, see how she feels about all this, ok? I sputtered out.

Jill instantly relaxed and slid back in her chair with relief. "Thank you so much for your time and consideration Andy! If you would be willing to help us out, I can promise you won't regret it! Promise, promise, promise! I'll get out of here now so you can finish enjoying your evening." Jill was elated with the turn of events and could hardly contain her building excitement. She had broken through my reluctance and wanted to leave before I changed my mind.

As she stood up and hugged me around the neck, she whispered "thank you" in my ear and I took in her scent for the evening. I couldn't help but gaze at her stunning figure in that snug dress just one more time as she pulled away. She caught my eyes wandering up and down, sizing her up and gave me a demurred little lip bite while handing her coat back. I walked behind her to the door to get one last look at that incredible ass sway back and forth.

"Here, same time tomorrow?" Jill asked.

"Sounds good" I closed the door behind her, and my cock was swollen and in need.

__________________________________

I just stood there at the door for a minute thinking about what just transpired. My plan was to halt this, and now I have this unknown excitement brewing in my stomach. My cock was starting throb thinking about the possibilities.

Once I get home to settle in for the evening, I always get out of my jeans and lounge around the house in pajama bottoms, a T-shirt and house shoes, so I headed to my bedroom to get comfortable. Standing in front of the mirror, I take a quick inventory of myself... I'm not a bad looking guy and being in construction work for 20 years I was still as fit as I was at 30.

Clothes changed, I headed downstairs, poured myself a premixed cocktail from a batch I had in the fridge, got comfy in my recliner and flipped open my laptop to surf some porn. I needed to bust a nut badly. I hadn't been with a woman for quite a while, so I tended jerk off a couple times a week to some online porn, and I had gravitated to blowjob-oriented videos. Mostly women in POV positions with eye contact sucking cock had become my go to, what really tripped my trigger.