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My Older Neighbor

Bob Long

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You know how everyone has had one of those dreams where they were naked  or almost naked and caught in a compromising situation, well mine was real. When I was sixteen give or take I had a girlfriend who lived three blocks from me, one night we were alone in her house drinking and we both had a really god buzz on and were in her bedroom getting down to business when I was just getting ready to put my cock in her pussy there was the sound of a car pulling in the driveway and the garage door going up. So, I did the only thing I could do, jump out her bedroom window fortunately for me it was on the first floor in the back of the house. I jump out and followed by my cloths well most of them anyway. I gathered up everything and proceeded to get dressed in my half drunken stooper, in the dark I managed to put on my T-shirt and sneakers and grabbed what I thought was my underwear but in fact were her red panties, but no pants. I could hear voices coming from inside the house, so I figured I had better get going while I still was able, so I headed off back to my house. Hell, it was dark out now maybe around midnight and it was only three blocks in a quiet residential neighborhood in my drunken judgement told me no problem I could do this. Yeah well that was not so easy, as I stumbled and crawled my way home because Jack Daniel’s had another idea, but I had finally made it to the only intersection I had to cross, well my timing was off slightly to say the least if I had waited a few minutes or had the smarts to get off the road and undercover of some shrubbery I wouldn’t have gotten caught in the headlights of a car making a turn on to the street. I had to be some sight I must admit, if getting caught literally like a deer in the headlights wasn’t bad enough the car slows down to a stop and I hear my name being called Bobby is that you the voice called. I didn’t know what to do run freeze dive in the bushes I was frozen with fear when the voice said get in the car right now.


 I did as ordered and when I got in much to my shock and surprise it was my neighbor from across the street Helen. She was a nice lady a widow whose kids barely came around so my mom decided we mainly me would pick up the slack and help her with things like mowing the lawn and shoveling the snow etc. So I’m sheepishly sitting in the passenger seat not paying must attention to anything other than the floormat she’s asking me so what happened to you I started to explain and she is laughing hysterically she puts her hand on my knee saying the same thing happened to me way back when but I don’t think my boyfriend was wearing my panties laughing. I must have turned as red as the panties and she laughed again with her hand on my knee saying its ok sweety you look really cute in them and this will be our secrete don’t worry your mom will never know. Not realizing what was happening at first but she began stroking my left thigh when she says oh my Bobby you look so uncomfortable all stuffed in there when she grabs my cock covered by my girlfriends panties. She said oh my, my you’re a big boy Bobby.

(now a little backstory on Helen she was a window whose husband happened to be named Bob as well, she was a retired teacher and the local neighborhood gossip was that her father who was very wealthy passed away leaving her a fortune why did she stay in our middle class neighborhood well she always told my mom she loved the people and quaintness of where we lived, I never looked at her in any way other than the older woman who lived across the street who was always very nice to me and always had a smile)

I was dumbstruck both in part of my alcohol induced state as well as I couldn’t believe that the nice older lady from across the street hand a grip on my now pulsating cock. I must have been enjoying the feeling because she said oh wow, you’re getting even bigger someone must be really happy. Unknowingly to me she drove right past our street, when I realized it, she smiled and simply said shhh Bobby its been so long since I’ve held a man’s penis it hasn’t been since my Bobby before she could continue hearing a little emotion in her voice, I said its ok. I just want to hold it for a while is you don’t mind its been so long and I don’t want anyone to catch us please understand, again I told her its ok Helen really its ok.

Still holding my cock with her right hand, she drove down the street and crossed another intersection and continued to drive a little to the reservoir which in reality was probably about a quarter mile down the road and making a left turn onto a dirt road which lead to a small brick building and a locked gate. She smiled saying don’t go anywhere sweety. She opened the door and standing at the gate she opened a little box and next thing I know the gate opens and she hops back inside and after we drive though the gate closes behind us. She looks at me saying I hope you don’t mind but nobody will disturb us here. I used to sneak here with my Bobby a lot when he worked midnights.

 (Bob was a Captain with the water company police and was known around town as a real hardass, but he was always nice to us kids on the block, played softball and football on our front lawns etc.)

 Helen pulls around behind the building and turned the car off but leaves the radio on. Bobby its been so long I hope you don’t mind and before I could utter a word, she pulls my cock from the chocking restraints of my girlfriends panties. It was so much of a relief it must have shown on my face, in a very soft sensitive voice she coed now doesn’t that feel better Bobby, all I could do was let out oh yes it does Helen. She was gently fondling my cock saying oh your poor guy your girlfriend left you unsatisfied didn’t she, you poor baby. Bobby you must get a lot of girls with this beautiful penis its magnificent, All I could muster was thank you she proceeded to ask me again, so do you have lots of girlfriends. No, the girls in my school are all cock teasers. I was shocked that I said that to her and immediately apologized saying I’m sorry I shouldn’t have used that kind of and she put her finger to my lips telling me its ok trust me we had those girls when I was in high school too but I’m not like that Bobby I’ll never leave you unsatisfied. Without warning she removed her black rimmed glasses placing them on the dashboard asking me do you mind and before I could utter my approval, she proceeded to go down on my cock putting it in her mouth and began sucking and slurping, kissing it and licking it to full erection. I moaned and said by all means Helen feel free to say I was in heaven was an understatement, she kept taking brakes from sucking me telling me how magnificent my cock was. Saying Oh! Bobby can I be your girlfriend I’ll always make you happy. All I could say was sure you can be my girlfriend. My drunken state was now replaced with complete euphoria. I had gotten a few blowjobs back then, but nothing compared to what I was experiencing. She said Bobby I’ll make you very happy I promise I love your big fat cock. I can do things to you those little tramps couldn’t even imagine. I liked what I was hearing for sure, she said there is nothing like an experienced woman Bobby, I’ll take you places and show you things you never imagined existed. My first thoughts were oh she wants to take me to places meaning vacations or shows or whatever, but sexual erotic experiences were the places she meant


 She sucked and slurped and licked me to heaven she had cock sucking skills like I had never experienced and even to date she is one of the three best I’ve ever had. She took a short break from sucking my dick  to lift her shirt up over her head revealing a super fine pair of 36DD tits I couldn’t believe what I was seeing they were fucking perfect. I was like holy fuck Mr. Boyd  she smiled and said you like them Bobby I was stuttering oh man she smiled and said don’t call me Mrs. Boyd, call me Helen or anything you want to baby; with that she had both hands behind her back unclasping her bra freeing those magnificent tits. The flopped free of their bonds exposing nice pink silver dollar size areola with nice hard pink nipples about half the length as my thumb and as big around. I instinctively grabbed her tits and began playing with them, gently squeezing and playing with her nipples. She took my hands saying Bobby I like them squeezed nice n hard and pinch my nipples please. I did exactly ask she asked and when I pinched her nipples she winced with pain and let out a loud yes Bobby yes like that oh place suck my titties. I sucked them both with a vengeance, she let out moan after moan which got increasing louder. She had her hand in her skirt and was squirming, she blurted out I need your cock I need you to fuck me Booby please fuck me with your big fat cock. My nice lady across the street had turned into a filthy mouth whore right before my eyes, the kid of things guys dream about.  Her undid the button and began to wiggle out of her skirt or at least I thought it was a skirt saying help me get this off Bobby.as she was panting and squirming as I  pinched her tits. I grabbed the waistband and pulled down to revel a skirt with pant legs? I was like what the fuck are these thinking to myself I was to find out much later it was all the rage back then. She was moving around and said wait and made her way to the backseat and lay there with her legs spread saying come fuck me Bobby please fuck me with that big fat cock please. I had to be part contortionist in a Mustang II, but I made it to the back seat and plunged my cock into her with one thrust being inexperienced and super horny and not at all aware that I possessed a much larger than average cock for a kid my age. Her eyes opened wide and she let out a loud gasp, oh my fucking God your cock is so big oh Bobby fuck me please Bobby. With every thrust I tried to go as deep and as hard as I could, her tits were flailing about and her face where racked with pain and pleasure form not having been fucked in over ten years a I was to find out later on that night. Not since her husband passed away had she hand sex and confessed that she lusted after me and some of the other boys in the neighborhood fantasizing about being ravaged by us, having her cloths torn form her body and being fucked and forced to do our bidding. As I fuck it became apparent to her that not only was I inexperienced but that I was in an extremely awkward position not fully enjoying her. Little did she know I was having the time of my life. She blurted out stop, stop honey please get off of me. I was like oh fuck what did I do. She smile and said let me fuck that big fat cock. She had me sit in the passenger seat and recline it all the way which brought it almost completely horizontal, she then hovered over the top of me grabbing my cock slicked wither juices and guided it back into her pussy. She slowly lowed herself down onto my rock hard shaft and her face was beaming. Oh! Bobby your magnificent you have such a wonderful cock it feels so good.


 I looked into her eyes saying oh your so fucking hot Helen my God I had no idea you were so damn beautiful and so sexy, oh Bobby your going to make an old lady blush. I said old fuck your hot. All truthful words see Helen dressed very modestly never ever showing even a hint of cleavage or anything flattering showing off her gorgeous figure well at least to us kids and the people in the neighborhood but I she would later show me tons of photographs that were to say the least quite the contrary the Helen in the photos were form her youth and if a very sexy alluring young woman dressed to kills. Later we would make many memories to be caught on film. Helen skillfully rode my hard cock slow and steady going deeper and deeper occasionally hitting her cervix which I later learned  was evident by the change of expression on her face. Even though she had two grown children and was close to three times my age her pussy was remarkably tight, she later told me that was due in part to her not having sex for so many years and plus I had a cock like a bull according to her that filled and stretched her so much she admitted that  back when she was a young lady she would have most likely runaway seeing such a big cock (big ego booster maybe) but now if she wasn’t so horny she never would have tried taking it in her pussy. She continued to ride my hard cock and had a look of pure pleasure on her face when I wasn’t grabbing and pulling at her tits and nipples they were bouncing up and down and that instantly brought a big smile to my face. She said so you like watching my boobs bounce up and down huh, I smiled and saying yes, I do so, oh really do you now[B1] , we’ll see how you like this, she leaned in and smothered my face wither titties slapping my face with them laughing as I tried to get one in my mouth. She grabbed both my wrist and held my arms as she slapped me with her titties laughing. She stopped and said Bobby I just love fucking you me too was my response. She smiled and immediately got back to business and increased her rhythm and picked up the pace she began sweating and her face and tits were glistening in the moon light, her beautiful tits rhythmically keeping time wither thrusts. She began moaning and muttering oh yes Bobby yes, I’m cumming  Bobby I’m going to cum please fuck me harder, so I did my best to meet her thrust by holding her by the waist and thrusting upward shoving my cock into her pussy. She now let out a series of screams I thought enough to wake the dead Oh fuck me with that big cock you mother fucker oh God I’m cumming Bobby and before she could utter another breath her body began to shutter and shake like she was having an epileptic seizure. Seeing this not knowing what the hell was going on I stopped pumping my hips when she screamed no fuck me harder! Harder, dam it don’t stop please don’t stop was the last thing she said as she began to shutter and shake, and I could feel her pussy tighten and grip my cock. Her eyes were closed, and she kept pumping my cock. She slowly decreased her intensity but still kept fucking me and I could feel her pussy gripping my cock and the next thing I know is I can feel this hot sensation in my ball and my cock like It was on fire and was building pressure. I knew the feeling all too well as most guys my age did from jerking off, she being an older more experienced woman kept up her pace asking are you ready to cum for me Bobby. Oh yes, I’m cumming baby I’m cumming all of a sudden, a look of shock must have come over my face and clear as crystal I said I’m not wearing a rubber, she placed a finger to my lips shh I want you to fill my pussy full of your cum Bobby. I started panting and could feel myself getting ready to explode trying my best to hold back prolonging this fantastic feeling, but it was no use, Helen said com in my pussy Bobby cum for me I want to feel your hot load. I could feel my hot steamy load erupt from my swollen cock. I felt hot steamy load after load pump from my cock thrusting my hips driving my cock as deep into her pussy as I could. I pumped so much cum into her pussy that I could feel it oozing past my cock escaping from the tight grip of her pussy. I pumped her for what felt like fifteen minutes, but truth be know was probably much less, but I was determined to empty every once of my cum into her pussy like she asked.


 When I was finished pumping her, I was spent she stopped fucking my cock and just sat on top of me telling me she was savoring the feeling of my cock buried inside her. Looking at me she said I hope you don’t mind, I smiled at her saying no not at all keep me in as long as you want. Looking up at her I was gazing into her eyes and I could not believe  that I hadn’t noticed her beauty before. I softly touched her cheek saying I was sorry, she said sorry for what this, what just happened. I did what she did to me and placed my finger to her lips and said no I never knew how beautiful you are. She said your so sweet but your going to make an old lady blush you didn’t have to say that. I said no its true I swear Helen your so beautiful your eyes your hair your pretty face but I never. She smiled and said never noticed anything more than a frumpy old lady across the street. By my facial expression she knew she was correct, its ok Bobby its just me its who I am. When I was married my husband did not want other men looking at me lusting after me as he used to say, I belonged to him I was his and his only. I was shocked to hear such a thing but looking back at that time and now realizing that maybe Bob really was a real prick after all, I just said what popped into my head, well if you were my girlfriend or wife I’d want to show you off not hide you in a closet. She leaned in and began kissing me on the lips and cheeks saying Bobby your such a sweet boy why couldn’t you be a little older, why couldn’t I be a little younger. I said so what who care, she said Bobby your such a sweet boy and so innocent if people found out what just happened I would most likely be run out of town or maybe go to jail my only response was fuck that. You asked me earlier if I would be your boyfriend well do you want to be my girlfriend, I asked she smiled and said yes Bobby I’ll be your secret girlfriend, but we can’t tell anyone not any of your friends do you understand Bobby she asked. I said I do Helen I really do, and it can be our secrete. She laughed and said oh my I still have your beautiful cock in my well fucked pussy, I smiled, and she said nice job young man if I do say so, but I have so much I want to teach you. Sure, with a big smile saying hey you were a teacher right so who better than you right. She smiled and kissed me and leaned in resting her big tits on my chest saying yes Bobby I will be the best teacher you could ever ask for. I did what came naturally and stroked her hair and hugged her pulling her close to me, I could tell that she hadn’t been held or hugged probably since her husband dies and maybe not even then if he was as big of a son of a bitch as he sounded. She said hey let me ask you did you enjoy me sucking on your cock, I said of course I did it was fantastic. Have you ever gotten a blowjob before form one of those little tarts you go to school with? I said yes, I have a few times, but nothing came close to what you did Helen she smiled and then said did they swallow your cum, reluctantly I said no never. She smiled and kissed me and said oh well prepare for that to all change. As she dismounted off my cock somewhere between half flaccid and half hard she stuck her fingers in her pussy and it looked like she was scooping my cum from her pussy then immediately put hem in her mouth sucking her fingers cleaned repeated going back several more times, she looked at me with this wickedly sexy taunting grin saying I just love the taste of cum Bobby and yours tastes really, really good.  She then went down on my cock sucking and slurping like she had done earlier but this time she was doing her best to take me all in her mouth. She stopped for a second saying I want that big cock all the way in my mouth I want your cock Bobby, I smiled and said go for it Helen and much to my surprise she got a little more than half to three quarters of it on her mouth. I placed my hand on the back of her head trying to force her to take it all and she willingly accepted my hand but as much as she tried and with me growing harder by the second it was apparent that she was not going to be able to  and I just held my hand there as she bobbed up and down, she squeezed my balls but not to signal me to stop holding her head because as soon as I let  go of her head she grabbed my wrist and placed it back on her head telling me it was ok. I held her head firmly but gently as she bobbed up and down on my cock. She began stroking my shaft as she sucked and slurped as much as she could. Now she was one very experienced and talented cock sucker there was no doubt in my mind and she continued working my cock like it had never been worked before she was twisting her head as she sucked her tongue working the head of my cock and every once in awhile she would remove it from her mouth to lick the shaft up and down and lick and suck my balls. How that Bobby I bet no little high school wore ever sucked your dick like that. Fuck now was all I could say, do you like it Bobby do you like how I suck your big fat cock. Oh yeah baby I do, then tell me. I love how you suck my cock Helen I really do, she looked at me and said be forceful Bobby I’m yours now tell me now make me suck your cock I’ll do what ever you ask of me Bobby. I didn’t come over me but I took her advice and said suck my cock bitch, grabbing her hair suck the cum from my balls my little whore, you want to be my whore don’t you Helen, Oh yes Bobby I’m your whore your old slut use me Bobby treat me like the wore that I am. I grabbed her hair and forced my cock into her mouth and made her continue to suck my cock well truth be told there was no making her do anything she willingly gobbled my cock and sucked and pumped my shaft and now she increased her stroking and sucking and I could feel myself building up another load of cum. It didn’t take long before my body began to shake and shutter just like it did when I blew my load into her pussy. I began moaning I’m cumming baby I’m getting ready to explode Helen still giving her the change to back off but true to her word as I began to shoot hot streams of cum from my cock, she sucked harder and pumped my shaft milking every drop of cum from my balls until I let out a series of grunts for my final eruptions of spunk. She never relented and kept sucking and milking my shaft. The head of my cock was now super sensitive almost to the point where I wanted to pull out of her mouth, but she was having nothing to do with that and only released her the grip of her hand and mouth when she was good and ready. She smiled and licked the cum from her lips, now Booby that how your supposed to have your dick sucked. I just exhaled and said yeah well, I have never had anything like that before Helen she smiled and said there’s plenty more where that came from Bobby. I just smiled and looked at her she kissed me saying oh my sweet Bobby you have no idea what you’ve done for me tonight even if we never and I stopped her said the only way your going to get me to sop is your going to have to ask me too, I want this Helen I really do. She kissed me and hugged me kissing me more and she sat up and looked at me saying hey you’ve seen me totally naked so fair is fair and she peeled my T-shirt up over my head, exposing my chest, being an athlete and training for my ultimate goal of being a US Marine I was in better than great shape Helen began to fondle my chest smiling saying oh my, my you do have some muscles now don’t you and without warning she pinched both my nipples laughing at the shocked look on my face. She smiled and said now let Helen kiss them and make them all better, as she proceeded to kiss and lick my nipples, something I had never experienced before. She did this for a little while when she grabbed my twitching cock. Oh, my look at you ready to go again so soon, looking back one of the benefits of a youthful libido, holding it she laughed and said oh as much as I want it again, I think its best we get you home before the sun comes up. I hope they’re will be another night real soon. I smiled and said how about tomorrow night, she kissed me saying it’s a date. Now we have to get you home, but we have one little problem me looking like a Dimmitt, she said you weren’t wearing any pants when I picked you up Bobby. Oh yeah, she said you let me take care of that. She proceeded to try and get dressed with me pawing at her tits and pussy making her laugh and then I hit the right spot and she began laughing I found her tickle spot and proceeded to torture her a bit, until she said if you keep that up I am going to pee myself Bobby.

 I did as she requested and after getting dressed, she put her glasses back on and pulled a hairbrush form her bag and brushed her hair to a somewhat presentable condition not looking like a woman who just fucked her brains out with a big dicked sixteen year old. She started her car and backed out and headed for  the gate and ran out and punched in the gate code and we left our secluded spot which we would visit may more times in the week to follow. She held mt hand and said Bobby that was fantastic, and I loved every second of it but I’m not going to hold you to anything, and I swear I won’t tell your mom. Hey what are you dumping me already, I told you I want this I want us she smiled and said you just made an old lady very happy Bobby. I said hey stop with that old lady stuff will you. Ok deal she said we drove to an all-night Walmart a few towns over and she said let me go grab you a pair of sweat pants oh fuck that what size waist and inseam are you, I told her my sizes and within maybe ten minutes she returned with a pair of jeans some socks and a pack of tighty whiteites. I got dressed on the ride back home and she we parked up the street and necked for a while me copping feels of her big tits and slipping my hand under her blouse and pinching her nipples. She came up for air and told me if I kept it up, she was going to fuck me right here almost in front of my house. I reluctantly relented and stopped playing with her tits. She kissed me saying you can play with them all you want tomorrow night that is if we still have a date. I kissed her deeply and said try and stop me, she told me she would talk to me tomorrow. She would call my mom and make up something as she knew my mom all too well as she would immediately volunteer my services. She smiled wickedly and said yes, I require your services young man tomorrow. I kissed her again as I got out of the car one last feel up her tits and said I’m yours.

This was the beginning of a four plus year relationship with Helen only secrete when we were both at home but there were multiple occasions where we were out of town or state and the threat of being recognized was nonexistent. Heck she even asked my mom if I could accompany  her to a friend’s wedding, my mom was somewhat hesitant and said well its up to Bobby, I casually said sure Mrs. Boyd I’d be happy to go as your date, with a slight smirk on my face that my mom couldn’t see because she had told me to never call her Mrs. Boyd but to call her Helen. She laughed saying well Bobby if we’re going to be my date you can call me Helen. Yes frumpy old Helen dressed in her typical house dress black rimmed glasses and housewife hairdo she was as non-threatening as she could possibly be, but when my mom excused herself to go to the bathroom, Helen quickly unbuttoned her blouse revealing she was wearing a sexy black satin bra with lace trim and as she buttoned up her blouse she mouthed the words I am wearing matching panties, all I could do was smile. My mom said don’t sit there with your mouth open ask Helen if she’d like some more coffee Helen wanted a lot more than coffee that’s for sure.



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What a hot story, my girlfriend and I were talking about some of our experiences last night after a wonderful night of sex. We wondered how many people out there has been in the same precarious position. She admitted back in high school to sucking cock in the locker room after a game and almost getting caught by the janitor, only to retire to the car to finish the job. As for me I was traveling and staying in a Hotel and had a close friend stop bye in the morning and if the maid knocked I didn’t hear it and she walked in to see my mouth swallowing his cock. Alittle embarrassing. 

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that one hot story wish it happened to me

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