My last set of encounters with Toni happened when I was 18, almost 19. I had started working a part time job, and soon after my 16th birthday I met my first girlfriend. We dated about eight months, never fooled around much. I broke up with her, and then went without a date for about six months. I met my second girlfriend at my job, a drugstore. I look back now and can see why I was attracted to Dianna, my second girlfriend, so much. Dianna reminded me a lot of Toni. They both were about 5 feet 5 inches, had long dark hair, dark brown eyes. They were both thin, around 100 - 110 pounds, had B, borderline C cup breasts, tiny waists, and perfect rounded butts. I dated Dianna for almost two and a half years. I was so in love with her. Our second summer together I kept up with it, and I saw her every day, for over 100 days. We eventually did almost everything sexual. Dianna did not want to give me a blow job, and I was not interested in anal sex. When I went to college was when we started having problems. Even though I was 45 minutes away, and came home every weekend to work and see her, Dianna got lonely. She soon found someone else, and dumped me. I did not know I could hurt so bad.
One weekend I was home, hanging around the house miserable, when my mom suggested we ride up to her mom’s for a visit. I grudgingly agreed and went with her. When we got to grandma’s, Toni and her friend Candi were there with Toni’s mom. I had not seen Toni, except during holidays, for almost 3 years. She was beautiful, she had filled out some, gotten taller, and was now 16. It was a beautiful early fall day, so Candi, Toni and I went outside. We walked around grandma’s farm, visiting the pond, the wood shed, barns, the creek, all the places we had played as children. I learned Toni had been dating a guy named Bob for about 6-7 months, and that he had recently dumped her. When the three of us were walking and talking, out of nowhere Toni had said “I sure had a good childhood… had a lot of fun here on this farm. “ Toni was to my right, beside me, and Candi was to her right, and had stopped to tie her shoe when Toni leaned in and whispered in my ear “ I wish we had more fun…” I was not sure what to say, I had not been paying her much attention, because I was hurting so bad from my break up. We continued walking back up to the house and up on the front porch, where we sat down on the porch swing. Candi started talking about Bob, Toni’s ex-boy friend. She was being kind of mean saying things like “ I would have never let Bob go, I would have done anything to keep a guy like that.” This upset Toni and she jumped up and ran off the porch, and up the path toward the road. I told Candi, “you stay here I’ll go get Toni,” and ran after her. When I caught up to Toni, I told her, “ hold up, don’t run from me… I don’t know why Candi was being such a bitch.” “It’s ok… you did not do anything… it’s just I’m hurting so bad and Candi had to say something like that… she’s my friend but she is such a slut, “ Toni sobbed. “Will it help you to talk about it” I asked, “you know my girlfriend dumped me two months ago… and I know how you feel.” Toni sighed and finally said “ I thought I loved Bob, and he loved me… but he was always pressuring me to do stuff with him to prove my love.” What kind of stuff?” I asked. “You know… he said if I loved him I would give him a blow job, or if I loved him we would have sex… that sort of thing, and when I didn’t , he dumped me.” “So what did y’all do together when y’all were dating,” I asked. “ I would give Bob hand jobs, and he would play with my boobs and my pussy. He was usually rough, not nice and gentle… like you used to be…” Toni blurted out as she stared in my eyes. I was stunned, “you remember that stuff?” I asked. “I don’t think I will ever forget how good you made me feel,” Toni stammered. “Bob hardly wanted to ever eat my pussy, and when he did he was too rough… all he wanted was a blowjob… or to fuck,” Toni stated. “So you are still a… virgin?” I asked. “Yeah… it just never seemed right with Bob… I almost gave in a few times… but he was so demanding… I felt like that was all he wanted,” Toni said. “I’m sorry you are hurting so bad Toni,” I said, “ I was thinking about what you said earlier… about us having more fun together… maybe if we fooled around like the old days, it would take both our minds off our pain.” I looked back down the path, Candi was trotting up behind us, about to catch up with Toni and I, since we had slowed to a walk. “If you and Candi were to come home with me, and after a bit I drove the two of you home, do you think we could get rid of Candi?” I asked. “What did you have in mind to do?” Toni asked. “I would never ask you to do anything you did not want to do, ever, “ I said. Toni thought a minute and said “Tell Candi when she catches up, that you will drive us home, and take us cruising. She will want to go meet up with a guy named Jeff she’s been after for a month, that hangs out at the car wash. You will say you will take me home as long as Jeff will take her home, and when she leaves with him, we can go parking some where private, and talk some more.”
Candi caught up with us and asked, “Toni are you ok, I’m sorry I did not mean to be hateful to you, I just …” I cut Candi off by saying “ Toni knows you did not mean anything, in fact she wants to know if I will take y’all cruising in your hometown, maybe you can show me the sights?” Toni chimed in, “Yes let’s take him cruising, maybe he will buy us beer.” Candi said “ that sounds great. We went back to the house and got permission for me to drive the two girls home. We left shortly afterward, I stopped at a country store on the way and bought a six pack of Clydesdale beer. Candi could drink, she had her 2 beers downed before Toni and I could finish our first. I told Candi, “you can have my last beer since I’m driving, and probably should take it easy in a strange town.” Toni finished her second beer, before we got to her hometown. As we neared the town limits Cindi said “Let’s see who is at the carwash first.” Toni’s plan was working, We cruised up to the car wash and Candi exclaimed “there’s Jeff in his muscle car!” We pulled up beside a jacked up two door coupe, and Candi jumped out of the car and ran over to Jeff and started chatting. I asked Toni, “are you worried we will run in to Bob?” “NO… he’s already dating a girl that lives in the next town over… he stays over there all the time,” Toni snorted. About then Jeff called over to me “Dude… if it’s ok I will take care of Candi.” I responded “ Sure… Toni’s bored, and there’s not much going on… so I’m going to make one circuit of the town, take Toni home… and head back home myself” I cranked up my two door Chevrolet and pulled up to the road, “where to, Toni,” I asked. “Act like you are taking me home… and I will tell you where to go from there,” Toni said.
I followed Toni’s directions and went toward her home, going out of town in the opposite direction. Toni had me stop and get 2 more beers at a small store, then directed me out to a nearby small secluded pond. “This is my other grandfathers farm… and no body ever comes back here,” Toni said. I backed the car up near the pond under the shade of an old oak tree, and left the radio playing low. “This is nice, “ I said. After sipping on her beer for a minute Toni asked, “ why did you start fooling around with me ?” I thought a minute and said “ well… I was curious about girls… and some how I knew that you were curious about me… and after I started, I really liked how you looked… and felt” I said. “Why did you let me mess with you?” I asked. Toni took a long sip of beer then said “Cindi and I talked about boys… about their things… and how they would stick up… and how she had seen yours one morning when y’all stayed at Grandma’s… and after that I was curious to see it myself… and when you started messing around with me… I kept seeing a bulge in your pants… so one thing led to another…” I paused and asked Toni “ what were you talking about back at Grandma’s… about more fun?” Toni said, “ I wish I had touched you and let you touch me, much sooner… that I had let you give me many more orgasms… that I had made you cum a lot more. “ I gulped my beer and finally asked “ what did you have in mind for this evening?” Toni thought a minute and responded, “ maybe what we used to do… what did you want to do ?” That was an easy question to answer with the mild buzz I had gotten. “ The same thing… just maybe… if you wanted… I would love to ear your pussy… I loved, loved, loved to do that with my ex… and I miss it.” Toni finished her beer and dove over the front seat of the car into the back and said “we’ll see where it goes.” I quickly followed her. I remember to this day, Boston’s song “More than a feeling” was playing.
I got settled in the back with Toni. I reached up and cupped her face, pulled her in and gave her a long, soft tongue kiss. I pulled back almost breathless and said, “don’t forget I don’t want you to do anything you don’t want to do” Toni breathlessly replied “I haven’t said no yet.” I took hold of her kissing her again and again, and started to caress her soft, supple breasts through her shirt. Toni reached down and pulled her peasant blouse over her head, as I reached behind her and with one had unsnapped her bra. I pulled back from her gazing at her two perfect mounds as her nipples finished stiffening all the way up. “I forgot what pretty boobs you have,” I croaked. My mouth was drying from breathing so heavily, my heart felt like it was about to burst from my chest, and my dick was about to explode it was so hard. Toni reached down and rubbed my dick through my jeans as I caressed both her breasts. Toni reached down and unsnapped my jeans, then snatched the zipper downward, thrusting her hand down my pants grabbing my dick. As I kissed her liked a hungry man devouring food for the first time in days, I pushed my right hand down to Toni’s crotch, rubbing her pussy through her jean shorts. Toni started making kitten noises, then pulled my hand away so she could take off her shorts and panties. I quickly threw off my t-shirt, and snatched off my jeans and under shorts. As soon as we were both naked, Toni looked down at my dick like it was a long lost friend. “You’re bigger than Bob was, did your old girlfriend ever have any trouble when y’all were having sex?” Toni asked. I answered “ Just a little at first… I could not put it all the way in… until she got used to it.” As Toni continued to stare at my dick, she reached down and started to run her finger tips up the shaft and across the head of my dick. I asked “ so Toni… you never went all the way with Bob?” Toni answered, “NO… I’m glad I didn’t… I jacked him off, he would finger me and sometime’s I would act like I came just to get him to stop… he was so rough.” “Sorry about that,” I answered. I leaned in and started to kiss Toni again, reaching down I started to gently rub her pussy. After a few minutes I could tell she was responding. Toni had slowed to a stop stroking my dick and her hips were beginning to move in time with my finger rubbing her pussy. “I’m about… about to cum…” Toni breathed. “That’s ok, you just enjoy it, “ I said. Suddenly Toni started to spasm into an orgasm. When she caught her breath Toni said, “that was great… better than I remembered… so much better than… Bob. Do you still want… to eat me ?” “I’ll only do what you want me to Toni,” I assured her. “now just lay back and relax, and I will take care of that pretty pussy of yours.” I came at Toni from her feet, but in the back seat of the car it had me hunched over so much as to be uncomfortable. “Toni, this has me scrunched up too much, I am going to have to come at you from the other way,” I said. I changed to kneeling in the foot of the car at Toni’s head, leaning over, I parted the lips of her pussy. It was framed in thin, dark brown, short curls. I looked down at the moistness oozing out, caught her scent, clean and inviting and started to lightly swirl the lips around her clit. Every so often I would buzz Toni’s clit directly, but lightly with my tongue. Toni would thrust her hips up to me. Toni reached over and grabbed my dick and started stroking it. She quickly slowed down and stopped, yet hanging on to my dick like it was a life line. Toni had began to cum again, this time harder than before, she was all but thrashing, and was clamping her thighs around head. Toni bucked and thrust against my tongue for what seemed like ages, and then was spent. Toni had never let go of my dick, and had it in a death grip. Before she started trying to crush my skull., looking back up her stomach I had noticed her gaze never left my dick. When Toni came back to life she said “ I have never, never, ever cum like that before… I think I passed out…” Toni slowly started to stroke my dick, and asked “ what’s a blowjob like, what does the girl do ?” I had to answer, “ I don’t know, my ex would never do that, she thought it would be gross if I shot off in her mouth… I told her I would let her know before I came… what I’ve seen on x-rated movies is the girl bob her head up and down, twirling her tongue around the head and up and down the shaft… while basically jacking the guy off with her hand… but I don’t know. “ Toni’s gaze never left my dick as she slowly, slowly stroked the shaft up and down. Finally she said “ I have never had an orgasm like the one you just gave me… and every time you have made me cum it’s been the best… I want to try a blowjob with you… I want you to feel like I felt… if nothing else to spite Bob.” “Only if you really want to. “ is what I said as my brain screamed” yes oh yes please.” Toni pulled me closer to her, and slowly gave the head of my dick a tentative kiss, then a quick lick, never ceasing to stare at it. “Now you tell me when you are going to cum,” Toni commanded. “I… I will, “ I blurted as Toni’s mouth engulfed the head of my dick. Toni started stroking my dick and bobbing her head, twirling her tongue. I was in heaven. Even though Toni had never given head before, she was an enthusiastic learner. I would like to say I lasted forever, but in a couple of minutes later as my nuts began to tighten , I told Toni “I’m getting… getting ready to cum.” Toni broke contact with my dick long enough to blurt out “Ok, go ahead baby, enjoy yourself.” Toni swallowed the head of my dick again and was rewarded a few seconds later when my hips started to buck and I shot pulse after pulse of cum into her mouth. When I had shot about 3 spurts into Toni’s mouth, she raised up and looked me in the eyes. Toni had a dribble of my cum dripping down her chin from the corner of her mouth, and she kind of smiled at me and then with a gulp… swallowed. I almost passed out. Toni then said “ Bob made me watch an x-rated movie with him… the girls did that when their men came… I hoped you liked it… I wanted you to feel good as you made me feel… I just hope I didn’t gross you out.” I looked at Toni as she wiped the cum off her face, and took a sip of warm beer, and I said “No, no, it… was, it was great, no girl ever did that for me, it was great.” With that said I took Toni’s face with both hands and drew her in for a long kiss.
After kissing and basically cuddling for a few minutes I asked Toni, “ would you like to 69, that’s where I eat your pussy, while you give me a blow job?” Toni looked down, and after a minute looked me in the eyes and said,” I would like to try that sometime… but what I really want… what I’ve been wondering a long time… ever since Cindy told me that a boy… could put his peter up in a girl’s pussy… ever since saw you get a hard on… is what you… would feel like… up in me…” I was blown away, speechless for a few seconds. I had never thought when I had hatched my scheme to get Toni alone, that I would have the chance to fuck her. But… “We can’t… I don’t have any condoms with me,” I answered. Toni looked at me with those big brown eyes and said “ I’m on the pill… mom got me on the pill after I started dating Bob… said she didn’t need any grandkids just yet… It’s ok I’ve been on the pill for over three months.” I felt my dick twitch back to life. I leaned in and kissed Toni some more. The crickets were singing, and the sun was starting to go down. As I kissed Toni I started playing with her breasts and nipples. After lingering with them a while I reached down to her clit. Toni said “careful I’m a little tender.” So I slid my finger in to the edge of her pussy, exploring in a circle its rim. I could feel her pussy gasping (pre- post orgasm ?) Slowly I slid one finger up in her pussy until I met a band of resistance. Her hymen, Toni was indeed a virgin. Toni had previously had two massive orgasms, and as such was sopping wet, fully lubricated. Toni had grabbed my dick, kneading it, coaxing it back to hardness. I broke our kiss and breathlessly asked her, “ Are you sure you want me to do this, and if so are you sure you want me to cum in you… I can pull out and…” Toni cut me off, “make love to me right now, right here… right now” I laid Toni on her back, pushed her knees up and apart, and said ‘if you are sure.” With that I took my dick in hand and rubbed it up and down in the opening of Toni’s gash. When I had the head of my dick fully lubed up in Toni’s wetness, I slowly pushed the head through her opening. I leaned forward and began kissing Toni, while I pushed my dick in and out of her. At first just the head slowly, then easing it deeper in, until about a third of the way, I felt resistance. “That’s you cherry,” I said, “this may hurt some, are you sure you want to go on Toni?” “I’ve… never felt anything like this before, I feel so full…don’t stop… please” Toni pleaded. I pulled back and quickly shoved most of my dick into Toni’s waiting pussy. “OH!” Toni blurted out. I lay still until Toni raised her head up with on small tear in her eye kissed me. After that I would alternate short strokes with deep strokes until I worked all my dick into Toni’s pussy. Toni broke from mindlessly kissing me to stammer, “ I want to… to… cum with…. You in me… if it won’t gross you out out… I’m going to rub down there… a little to help out… oh it feels so… good!” I almost lost my load right then, but I concentrated on the song playing on the radio. “That Smell” by Lynyrd Skynyrd. I felt Toni’s hand flutter between us as I increased my pace. Toni started arching her back, pushing up toward me, “I’m cumming…” she grunted. It was like trying to ride a bucking bronco. By now I was slamming my dick into Toni, my nuts slapping her butt. My nuts soon tighten up as I gushed my cum up in Toni’s pussy. I could not say words, just “OH, OH, OH, OH, OH!” Then I all but fell off Toni. I regained consciousness, and Toni was gazing in to my eyes, stroking my face. She said “that was better than my wildest dream. If I wasn’t sore from you popping my cherry I think I would like to try a 69” I said “that’s ok, it’s starting to get dark. We should probably go, maybe stop by McRonald’s and freshen up a little… besides maybe we can do that next time.
We had a long Indian summer that fall. It stayed warm up until Halloween. Toni and I had sex every weekend for about 5 weeks. We did almost everything imaginable. However we never had anal sex. But Toni did love to 69. It was always a race to see who would cum first. Toni got to where I could slide all of my dick in her with ease once she was lubed up. I had to make excuses for not going home on the weekends. I would tell my folks I wanted to stay up at school and go to football games. I told work I needed to be off for some projects and mid-term exams. I would ride to Toni’s hometown and pick her up at Candi’s. But after a while my grades started to suffer, and my money was running low. I really did have to get busy. Toni asked me if it was ok if she went with a guy to a Halloween festival. I told her, “ Sure, I knew you would probably start dating someone sooner or later.” Toni had helped me get over Dianna.
Weeks turn to month’s. The next thing it was the next fall. Toni was engaged to be married. I took my new girlfriend of six months to Toni’s wedding. At the reception I greeted Toni with a big hug and asked, “This guy Bob you married… is he the same one ?” Toni blushed and whispered in my ear , “Yes… I’ve had to train him in how I like things done… and by the way… You’re still the best man.” and winked at me. “Toni, you haven’t met my girlfriend Deanna… so if you won’t tell… I wont’ tell.” Toni nodded and winked again. Deanna stepped up and I introduced her to “my favorite cousin.” A little later after the crowd thinned out, I caught up with Toni at the punch bowl and asked her, “So are you still alright with all the things we did together?” Toni did not hesitate answering, “I know what we did was a bit wicked, but the only regret I have is… we didn’t do it a lot sooner, so we could have done it a lot more. Tell you a secret, if I really want to cum my hardest with Bob, I just close my eyes and pretend its you.” Toni blushed, I looked and saw the kitchen next door was empty, stepped in and verified that fact. I motioned for Toni to follow me in, and when she entered, I grabbed her and gave her a long hard tongue kiss. “Woohoo now I can give Bob a wedding night he won’t forget,” Toni said.
It was about 25 years before I saw Toni, first at my mother’s funeral. Then about 18 months later at her mother’s funeral. When I got to the reception line I told Toni, “I’m so sorry for your loss.” Toni looked at me and said “I’m getting good at loosing… Bob passed about a year ago… in a car accident.” Maybe it was my imagination but when I hugged Toni, I swear she briefly played with my ass. I still ride motorcycles, and have dropped by to see Toni a few times when riding. Toni told me the last time “ my youngest graduates this spring and is going into the Army… stop by after she leaves home… I’d like to ride with you again.”
Makes me wonder if she’s a lonely widow. Toni still looks good, just a touch of gray, kind of reminds me of my wife.