Cuckold in the Making, The journey Continues

It’s funny how you vividly you remember some incidents that you have no good reason to remember. Sometimes they are locked away for many years and suddenly, something triggers a mind dump and you remember it almost as though it happened a few minutes ago. This morning I was reading a story about a guy whose wife has cheated on him and instead of being angry he was sexually aroused. He said that several of his ex girl friends had cheated on him and he had the same response. When I read that last part, I had a memory dump o a day long ago. It was like a video was playing in my head.
A little background first: Until I was almost 21, I was a little shy with girls, always thought I was too fat and not very attractive because I wore bottle cap thick glasses and had unruly wavy hair. It wasn’t helped by the fact that I attended an all male Catholic prep school where the Jesuits held up the ideal that women were to be treated like they were the Blessed Virgin Mary. I guess I knew that some girls were sluts but honestly thought that most girls were not interested in sex. In short, I was a pretty naïve guy.
When I was in my late teens, I had a very serious but secret (At least I thought it was secret.) crush on Jackie D, a girl who lived up the street. Jackie was what you would call a willowy blonde, about 5” 5’ tall, 110 lbs, great legs (especially in the short-shorts that were so popular back then) and perky breasts. I would flirt with Jackie but she thought of me as big brother, and at the time this all happened she was not at all romantic toward me. Nevertheless, I was head over heels in love with her. When I think back I have no idea why I did my best to make her and everyone else around think we were just platonic friends.
Now for that memory that came back flooding my mind this morning:
It was a warm summer evening and I had some time to kill so I walked across the street to the park/schoolyard with a baseball glove and a rubber ball which was a little bit smaller than a standard baseball with the intention of honing my pitching skills. My younger brother and I used to play this two-player game we called “Strikeout “ and I was bound and determined to keep my edge. In the schoolyard, there was an area with a makeshift pitcher’s mound about 45 feet from the school wall. A box that represented the baseball strike zone was drawn on the wall with chalk. The pitcher would try to strike out his opponent or get him to hit a ground ball, an automatic out. If the batter hit a line drive or a fly ball, there were lines drawn in the oil-coated fly ash cinders that were used to determine if the hit ball was a single, double, triple or home run. Imaginary runners were placed on base and would have to be forced in by the successive batters. For instance, if there was an imaginary runner on first he would score on a triple or home run. An imaginary runner on second would score on a double, triple or home run.
There was a green picnic table about ten feet to the batter’s box where or guys and occasionally some neighborhood girl s would gather, That night when I started to pitch there were three guys, Jeff, Mark, and Barry at the table bullshitting about teenage guy stuff. I tossed the rubber ball at the chalk box. It missed hitting the strike zone by a couple of inches and bounced back to me. I repeated the process until I was warmed up and throwing consistent strikes. Looking at the table I asked, “Anyone up for a game?”
Barry answered, “Got a bat?”
I replied, “Left mine home.”
I wasn’t in the mood to go back home and get a bat so I continued pitching to the chalk box. As I did I heard Jeff start to boast about his latest sexcapades. My ears perked up because Jeff could spin a tale. You weren’t always sure that he was telling the truth or just bullshitting but he was entertaining. Let’s say that Jeff often embellished the truth. He was one of those guys that would start off with an actual incident and spice it up with something he imagined. To that type of guy, the fact that he imagined it happened, made it true.
Jeff started, “You guys remember last night when Jackie and Sharon and Sandy, the D twins were here? Remember when it was starting to get dark, I offered to walk them home. You know the D twins live on the other side of Delaware Ave. and they needed to be home at 8:30 so Jackie and I walked them home and then started up the street toward Jackie’s house. When we got to Delaware She asked if I minded if we walked behind the school and through the park instead of up Tacoma Ave. She told me she was in no hurry to get home because her mother was working that night and her older brother Pete had his girlfriend over. As we walked I reached out and held her hand. She didn’t push my hand away so we walked holding hands. As soon as we got behind the school, out of the street lights, I stopped and bent down to kiss her. She kissed back.
I thought to myself, “I was here last night and I remember them all leaving together and walking up Tacoma toward Delaware. A walk back through the park and a kiss was innocent enough even good girls let guys kiss them 55 years ago.
Jeff continued, “You know how full Jackie’s lips are. She really knows how to kiss. We strolled along and she told me she really didn’t want to go home yet because she hated being there when Pete was home making out with his girlfriend Kathy. She asked if we could sit on the back steps of the school building and talk. So we went over to the steps and sat down. She started to tell how once she walked into the living room while Pete and Kathy were on the couch and saw that Pete had Kathy’s blouse off and was feeling her up. She told me that they didn’t see her there and she watched her brother squeeze Kathy’s tits and pinch her nipples.
“I asked Jackie if Kathy enjoyed that and she said she thought Kathy did judging from her moaning and purring. Then Jackie said that she was so embarrassed to see them, that she quietly went to her bedroom and turned toward me hugged me, leaned over and cried on my shoulder. I asked her why she was crying and she said that she was jealous of Kathy and that she wished she was as sexy as Kathy and that she had a boyfriend too.”
Mark piped in, “Bullshit, Jeff! Is this one of your sob stories like with Marie where you just try to comfort her and she attacks you and sucks your cock or jacks you off? I checked with Marie’s brother, Jack and he says she was at her aunt’s house the night you said that happened.”
Barry and Mark laughed derisively, but I just kept pitching against the wall because I didn’t want them to think I was interested in Jeff’s story. Jeff was on a roll. He answered Mark’s question by continuing his story. “There we were on the back stairs and she was crying so I hugged her back. She looked up at me through her teary eyes and asked if I thought she was sexy. I kissed her on the forehead and told her that she was very pretty. Her arms went around my neck and she kissed me. She thanked me for saying she was pretty but asked again if I thought she was sexy. I asked her if she was serious and she nodded. I told her all the guys thought she was sexy but she had a reputation as a cock-teaser.
“She was shocked at my blunt answer. I don’t think any guy had ever said the word cock to her. She looked puzzled, so I explained: the short-shorts you wear, the way your ass cheek are half hanging out of them makes me and the other guys drool but you seem to have no interest in us. You never flirt with us like the twins do. You never date.
“Jackie started to cry again. She told me that she didn’t want us guys want you guys to think she was a slut like Marie and Jill.”
Barry whistled when Jeff mentioned Marie and Jill and interrupted, “How would Jackie know about them? I thought that they told us that they did not want anyone to know what they do back in the bushes.”
Jeff was a little pissed at Barry’s insinuation that he had been blabbing about their supposed secret. He snapped back in a loud voice, “How in the fuck do I know how she knows about Marie and Jill?”
I stopped pitching at the wall and yelled back. “Everybody in the neighborhood knows about you and them. Do you think we are all blind? You walk off into the bushes over there with one or both of them in broad daylight, and then an hour later you all come back with your clothes and hair all messed up. The girls all gossip about them all the time.”
The three of them laughed when they heard what I said and Mark shouted back, “So we are that obvious!”
I smiled knowingly at the three of them, nodded and went back to pitching. Mark and Barry might have been dubious about whether Jeff was telling them the truth but they wanted to hear the rest of his story. Mark said, “So what happened next?”
Jeff was still visibly pissed off at them and said, “First you tell me I am bullshitting. Now you tell me I blabbed about our secret. I don’t know if I should tell you more.”
Barry chimed in, “Yeah! Come on! Tell us the rest!”
Jeff relented, “OK, where was I?”
Barry relied, “You had just called Jackie a cock-teaser.”
Jeff agreed, “Yeah, and Jackie said she was that way so that she wouldn’t be considered a slut like Marie and Jill. I asked her if she thought that Marie and Jill were sexy. She said that she thought they were sluts and that could be sexy. I asked her if she knew what a slut was. She said that Marie and Jill were sluts because they went around with a lot of guys. She seemed to be avoiding actually saying that they fucked a lot of guys. I pressed her and asked her what she meant ‘they go around with a lot of guys.’ Again she danced around coyly saying they let the guys have their way with them. I teased her by saying what do you mean ‘Have their way with them.’ I asked her if she meant that they had sex with all the guys. She said yes that’s what I meant and she playfully punched me on the shoulder. Within a few minutes we were playfully wrestling. I was easily winning and copped a couple of feels. Man her titties were firm. She wiggled away from me and ran toward the park lawn. I caught up with her and grabbed her around the waist and turned her toward me. She laughed as I took her to the ground gently. We were practically at the bushes. We rolled around still wrestling and soon I got on top of her and had her shoulders pinned and counted the three seconds. I asked her if she gave up but she continued to struggle. I told her you lost the wrestling match. I pinned you fair and square now you must pay the penalty. She asked what the penalty was and I told her she needed to spend 30 minutes with me on the bench in the bushes.
“At first she said, ‘That that is where the sluts go with their guys.’
“I was still on top of her and told her that if she didn’t come with me to the bench she would just be acting like a cock-teaser again. I bent down to kiss her hard. I expected that she would try to resist and turn her head away but she kissed back. Not a light playful kiss like when we first got to the park but a passionate one. I pushed my tongue into her lips and she opened her mouth and our tongues pressed against each other. Man she has the softest lips and the best tongue I can’t wait until I get her to put them on my dick.”
Mark interrupted, “You wish! You pin a girl down and force her to kiss you and then think that in another day your cock will be in her mouth. I’ll bet you never had a blow job before, even from Jill or Marie, and they have sucked every other cock in North Buffalo.”
Barry laughed, looked over toward me, and added, “Well, maybe not every cock in North Buffalo.”
I felt a rush of adrenaline and testosterone at the insult, but instead of acknowledging it I kept pitching the ball against the wall. I felt a little ashamed but it was true. I had never got my cock sucked by Jill or Marie or anyone else. As a matter of fact at that time I had never even French-kissed or felt up a girl. I was, as I said, a good Catholic boy.
As always Jeff was not to be diverted from his tale by a mere insult. He continued, “I rolled off her and on to my side and she put her arms around me to hug me while we kissed. My arms were inside hers and the next thing I knew my hands were inside her blouse caressing the warm skin of the middle of her back. She seemed to be enjoying that so I moved my hands up toward her shoulders o the way up I felt the thin elastic back strap of her bra. I was tempted to unfasten it but decided not to take the chance that she would be scared and stop our little make out session. We broke off our kiss for a minute to catch our breath. She whispered, ‘That was nice!’
“Then she surprised me by kissing me hard, breaking our hug, and rolling over on top of me. Then she pinned me to the ground by putting one of her knees on each shoulder. She was there with her legs spread one knee on each of my shoulders. I could clearly see the crotch of her short shorts less than a foot away from my face. It was wet and wedged into her pussy. I stared at her pink lips peeking out of either side of the blue cotton crotch. I was ecstatic at the sight until she jolted me back to reality by quickly counting one, two, three. She said, ‘I win. Now you need to pay the penalty. You have to take me to the bench but you only get to show it to me.’
“I started to argue, ‘You cheated!’ but then I shut up and thought to myself, ‘I think she really wants to go to the bench and not just to see it.’
“My hands were still under her blouse and I took the opportunity to move them around and put one over each of her tits. I expected that she would slap my hands away but she let me feel her up outside her bra for about a minute. Her head went back and she seemed to be enjoying having her tits mashed. I decided to try for some bare tit but when I started to slip my hands under her bra she pushed my hands away, jumped to her feet and started to run across the field. She was not running toward her house, she was running toward the bushes.”
By now I was still pitching the ball mindlessly against the wall, thinking to myself, “Jeff can’t be bullshitting. He is remembering too many details. The fucking son-of-a-bitch is telling the truth. Just how far did Jackie go with him last night?”
While my mind had wandered, I missed a little of what Jeff was saying. When I was listening again he was saying, “When we reached the bushes Jackie stopped and turned toward me hesitating to go further. She was looking up at me with those pretty blue eyes of hers and then looked down toward her feet as if to say I am ashamed. I knew she needed to be reassured. I took her hand and said, ‘Let’s go take a look. I have never seen the bench either.’
Both Barry and Mark remarked, “Liar, liar your pants on fire. You were one of the guys who stole it from the playground!”
Jeff continued. “Yeah! I know but she looked like a deer in the headlights she needed a little encouragement.” Anyhow she seemed to be relieved and said, ‘OK!Let’s go take a look!’
“I guided her through the bushes but not directly to the bench because I didn’t want her to know that I knew the way. Instead I led her around to the small open area just beyond the bench where Jill and Marie usually set up the blanket. To my surprise the blanket was on the ground. We stopped and I turned Jackie toward me and kissed her. She responded even more than in the field. Her mouth opened and her tongue was inside my mouth before I could put mine in hers. Her hands were on my ass pulling my crotch into hers. My hands were under her blouse mashing her tits outside her bra again. She pushed her chest into my hands demanding more. I slipped one hand inside her bra from the top and felt the bare skin and when my finger touched her hard nipple, she broke off the kiss and her head moved backwards as she moaned, “Oh god that feels so good. Now I think I know what Kathy feels like with Pete.’
“We stood there and I kept on tweaking her nipple for a few minutes, until she said, ‘Aren’t we supposed to be looking for that bench?’
“I led her around for a few more minutes taking a couple of opportunities to French kiss her and feel her up. Finally I took her through the opening to the bench. She stopped for a second at the first sight as if to turn around and leave but I took her in my arms and kissed her. She kissed back and my hand was soon inside her blouse again. This time it was her other tit that got the attention. You should have been there. Her mouth was so hard on mine while we kissed; I thought I would get a bloody nose.
“I eased her toward the bench and we both sat down never breaking our kiss. I asked her. ‘Want to play a little game while we are sitting here?’
“She answered, ‘What kind of game?’
“I said, ‘When we came into the park, you said you wished you could be sexy like Kathy. Why don’t we pretend that you are Kathy and I am Pete?’
“She was a little hesitant, ‘I think that Pete and Kathy are having sex. I don’t think I am ready to go that far.’
“Being as smart as I am, I assured her, ‘We will not go that far and we can stop whenever you want.’
“She said, ‘OK. Where do we start?’
“I answered, ‘We can start by you telling me what you would like me to do. You said you watched them that time when Pete took her blouse and bra off on the couch. We could pretend it was us.’
“She said, ‘I didn’t watch him take her blouse and bra off. I walked in the room and she was already naked from the waist up and all she had on was panties.’
“I perked up, ‘Let’s start from there then!’
“She said, ‘If you think I am going to sit here on this bench in nothing but my panties, you are crazy!’
“’OK we can start where we are and I will be Pete and take your blouse off first.’
“I didn’t wait for an answer. I kissed her and felt her up a little and unbuttoned her blouse. She responded passionately and took my hand and placed it inside her bra cup. I started to play with her nipple again. She broke off the kiss long enough to slip her blouse off and toss it on the ground. She spread her arms across the back of the bench and pushed her chest out enjoying the nipple pinching. It was then that I felt proud of the decision we all made this June when we put the bench where it was dimly lit by the street light about 100 feet away on Hartwell Road. There she was in only bra. You know how Jill and Marie wear fancy lace bras. Jackie’s was just a plain white soft-cup cotton bra. I commented, ‘You look so sexy sitting there with just no blouse.’
“She said, ‘Shut up Pete! Kiss me!’
“I did as I was told and after a few minutes of French kissing and playing with her tits through the bra, I pushed her straps off her shoulders and out popped, her gorgeous tits. I dove down and started licking one nipple and then the other. Getting into my character in the game I moaned to her, ‘Kathy, I love your tits!’
“Jackie though her head back. She closed her eyes and moaned ,’Oh Pete I love the way it feels when you kiss them like that. Take my bra off now!’
“As I undid the clasp in the back, her bra came loose and slid down her arms. The first thing I noticed was that she had s distinct tan-line on the waist and the top. I asked her, ‘Kathy do you have a bikini?’
“She answered, ‘Pete, you silly boy. You know I do. You took me to the beach last Saturday with your little sister, Jackie. When you were scolding her for wearing that skimpy two piece, didn’t you notice that I was wearing a bikini too?’
“I stayed in character and replied, ‘Yes! Sorry Kathy but I was shocked that my baby sister could look so sexy. She is going to be a very popular girl. I don’t think she knows just how gorgeous she is.
“It was then that I noticed that Jackie’s tits were different than any I have seen before.”
Barry quipped, “Like you have seen thousands of pairs. You bull-shitter, the only tits you have seen up close, outside of watching your mother through a keyhole, are Jill’s and Marie’s. Playboy centerfolds don’t count. What makes Jackie D’ so memorable? They have always seemed a little on the small side to me.”
By this time I had stopped tossing the ball mindlessly and wandered over to the table. I had listened to the last part when Jeff was saying Jackie’s tits were different.
Jeff answered, “Believe me! They are pretty nice. Not huge like Marilyn F’s or tiny like Jill’s. I would say they were only slightly smaller than Marie’s. I peaked at her bra size and the tag was faded and kind of hard to read. I think it said 36C. What makes them different was the way they sit on her chest. Every other set of tits I have seen kind of start at the arm pits and hang down, Jackie’s seem to start just above her waist and push out and her nipples are very dark, almost a maroon brown and they kind of curve up and out slightly to each side.”
Looking over at me Jeff asked, “You have taken Jackie out, haven’t you?”
I stopped my mindless pitching against the wall, came over to the table and sat down next to Jeff. “Yeah, I took her to a couple of dances at school and to bars afterwards.” I boasted.
Jeff said, “Tell them I am right about her tits!”
I nodded yes. I think I did a good job hiding the fact that I had only just kissed her on those dates but never got close to seeing or feeling her hidden (from me) treasures.
Jeff continued his account confident that everyone now believed him. “After taking in their beauty for several seconds, my mouth latched on to the nipple closest to me and I sucked it hard. She moaned and started to squirm a little bit. As I sucked, her head was thrown way back and she was purring. She pushed her tit into by mouth like she wanted me to swallow the whole thing. My other hand was mashing her other tit. Then something strange happened. I don’t know why but she tensed up and shook a little bit and then went limp. It was like she passed out. I have never had a girl do that. I wonder if she had a fit. You know like Harry P has. Only after about a minute she seemed fine.”
I was about to tell Jeff that he had made her cum but decided to keep my mouth shut. If he didn’t know about female orgasms yet, it was not my job to enlighten him.
Jeff kept talking, “When she did come out of it she pulled my head off her tit and up to her face and whispered, ‘Pete that felt so good. I love it when you suck my nipples. Now it’s your turn, Let’s take off your clothes!’
“She proceeded to pull off my t-shirt and unbutton my khakis and unzip my fly. I pulled off my pants and was sitting next to her in only my jockey shorts which had a very pronounced tent pole in the middle. She then kissed me again but this time she would not let me touch her while we kissed. She was insistent, ‘It’s your turn Pete!’
“While she kissed me her hand went over the bulge in my Jockeys and she rubbed my cock from the outside. Then her hand went down the waist band and she started to rub my cockhead. After a couple of minutes she took my cock out of my pants. I could feel the precum leaking out and so did she. She giggled. Then she ran her thumb over the tip and used the precum as lube. Her fingers went around my shaft and she started to jerk me off. She did this for about 5 minutes but for some reason I couldn’t cum. She worried, ‘Pete, when I do this you usually squirt right away. What is wrong?’
“I didn’t know what was wrong. I guess I was nervous. I said, ‘Kathy, sometimes it helps if I play with my nipples when I stroke myself.’
“Jackie took my suggestion and used her other hand to pinch my nipples. ‘Harder!’ I ordered.
“She pinched very hard and I could feel the jizz building inside me. She then surprised me by taking my nipple in her mouth and biting down on it. In seconds I was shooting cum all over. I was drained and it was very quiet as neither of us knew what to say. I finally asked ending the game a, ‘Jackie where did you learn how to jack off a guy?’
“She answered, ‘Before, I told you that I saw Pete and Kathy on the sofa. I have actually watched them many times and some of Pete’s old girlfriends too. There is a mirror in the dining room that lets me see the sofa while I am lying in my bed.’
“I tried to kiss her and play with her tits again, but she pushed me away and said, ‘I have had a lot of fun tonight but I don’t think I want to go any further. Maybe some other time.’
“I felt bad and confessed, ‘I want you to know that I had a great time too. But I didn’t tell you the truth when I said that I had never been to the “bench” before.’
‘She cut me off, ‘I know I have seen you come back here with those sluts, Jill and Marie a few times and all of us girls have heard their stories about what goes on back here. Oh my God! I called them sluts but now I am a slut too.’
“She was almost in tears, but I took her in my arms and said, ‘Not a slut. Just a very sexy girl!’”
Barry, Mark and Jeff laughed at his last line and all agreed that Jackie was now a slut. I sat there quietly feeling somehow betrayed and yet aroused by her slutty actions. It was the first of a few occasions when Jackie broke my heart.
I went home and went directly to the unfinished stone walled basement where I could be alone and cried. My heart ached but at the same time the image of Jackie on the bench naked from the waist up with Jeff sucking her nipples made me hard. I undid my belt and fly, pulled my cock out and started to stroke it. It was then that I realized that I couldn’t cum all over the concrete floor. I looked around for a rag and at first; all I saw were greasy paint rags. I then saw the clothes hampers. (Our two-family house had laundry chutes from the living area down to the basement where the washer and dryer was.) I went to the tenant’s hamper and carefully opened it so that the dirty clothes wouldn’t all tumble on the floor. Luckily there weren’t many clothes in the hamper. Sitting on the top of the small pile were a pair of Rae’s (our upstairs tenant) shear pink nylon panties. I had seen that type of panty before hanging on the clothes line on laundry day along with a matching baby doll top when I was a few years younger and had a habit of going to the basement for solitude LOL.
On those occasions I had always brought tissues to catch my cum. By now I was desperate to cum, so I grabbed the pink panties and wrapped them around my cock so that it slid across the gusset. I was surprised that the gusset was already slimy. Within a few seconds, I realized that Rae had just been fucked and that the cum had leaked out of her pussy into those panties. The feeling of another guy’s cum on my cock combined with the image of Jackie on that bench pushed me over the top in exactly three more strokes.