Gail and Jimmy

Story Info
A gay man falls in love with the girl next door.
8.3k words
4.45
2.6k
4
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Hi my name is Jimmy and this is the story of why a gay cocksucker like me married a woman. I never felt comfortable around girls, the normal stuff before my teen years. But after puberty I still wasn't attacked to them. When I was twelve, I started going to the Amusement Center on Washington Street in Downtown Boston. I loved playing the pinball machines and became good at it. It was nineteen fifty-nine and it was not uncommon for a kid my age to ride the MBTA alone. I had money that I earned from my two paper routes and doing what was called supping the Sunday papers.

Supping was putting the Sunday paper together ahead of time, everything except the news section that was added early Sunday morning for the home deliveries. Also, to earn money, there were two double three decker houses two doors from my house. These were what was called cold water flats. The twelve apartments were heated by the coal burning stove in the kitchen and kerosine space heater in the living room. Eight of the units had elderly tenants and they would pay me to haul the coal and kerosine from the basement to their units.

It was only small change but remember for a nickel you could ride the bus get a transfer slip and ride anywhere in the city, by keep getting transfer slips. Candy was a nickel as was a bottle of soda. So, for a nickel I could go downtown and back for a second nickel. The pinball machines at the Amusement Center were also a nickel and once I got good enough, I won free games. Back then with two dollars I could spend the day and go home with some change.

By the time I was sixteen I knew all the regulars and would play for money, high score wins. I would win way more than I would lose and it wasn't long before most would no longer play against me. But they would help me hustle new comers for a piece of what I took them for.

When I was fifteen, I was going to Roslindale High and the girl next door was my age and going to Saint Claire Girls High School. It was on Cummings Highway across from the Sacred Heart Church. Her name was Gail and the only girl I talked to. We would walk to the Village, that is what everybody called Roslindale Square. We would stop at Cuddy's Donuts and most days she didn't have enough money to get a hot chocolate and a donut. I would buy three and give her one because I felt bad for her, her parents weren't the best in providing for their kids. Her dad drank and gambled. Her mom was not much better, the kids were on their own in the morning and Gail had to get them up and find something for them to take for lunch. Often breakfast was dry cereal because there wasn't any milk.

One morning she was very upset and it took a while before she told me what was bothering her. When she did it pissed me off, the guy she was going out with had asked her to his prom, which was my prom also. I had to give her mother credit; she did buy Gail a dress to wear. Now the guy told her if she didn't put out for him, he wouldn't take her.

I asked her: "Who are you going out with?"

She said: "John Chase.

He went to Rozzie High with me and I I know he was going steady with another girl. The dirt bag was using the promise of the prom to have sex with her. He had no intention of taking her.

I told her: "Look I wasn't going to go to the prom, but now why don't I take you and if you want, I will go to yours with you also. John can just go jerk off, because his steady girlfriend's father, would bust him up if he ever found out he had sex with her and he knows it."

So, we went to both proms and my friend Ken's dad owned several classic cars and he let my fiend use one to drive us to the prom. It was a vintage Rolls Royce and Ken wore a black suit and even had a chauffeur's hat. At that time no one rented limos so we were the talk of both proms. Several of the more popular girls slipped me their numbers. Little did they know I would have rather had their dates numbers.

When I turned eighteen one day the Amusement Center wasn't open because of an electrical problem. That left me with two options, Bond Billiards or go to the movies. I decided on the movies, but which one there were several theaters along Washington Street. As I was walking past the State Theater which showed adult movies. Back then there wasn't hard core sex movies yet, just nude men and women with a weak story line. You had to be twenty-one to be admitted, but I figured I had nothing to lose in trying to buy a ticket.

I put a dollar on the counter and the guy gave me a ticket and fifty cents change. So, I was going to see my first adult movie, I was excited. The star was a woman named Bunny Yeager; I was disappointed she didn't take her clothes off. She was a photographer and, in the movie, she was helping a teenage girl in her late teens to become a model. The girl was shy and it took a while before she posed in her bra and panties. As she relaxed, she changed into a bikini and then see thru nighties and finally she posed topless. From there the scene changed to an out-door shoot and the girl was now comfortable getting naked and posing for the camera.

While I liked looking at the girl naked it didn't excite me sexually. As the credits were rolling, I needed to use the bathroom and went to find it. It was down stairs and there were a couple of urinals and two stalls. The only thing open to use was one of the stalls. When I went in, I saw the partition between the stalls had an almost foot square hole in it. I thought that was weird and since the person in the other stall could watch me pee, I sat down. I heard him moaning and thought something was wrong with him so I looked through the hole. He was stroking his cock and it was big and hard and seeing it made me hard. I leaned back and started jerking off, next thing I knew he reached into my stall and started jerking my cock.

After a minute he put his face at the hole and told me to stick my cock into his mouth. I had heard about blow jobs, but never had one. His mouth felt wonderful and I was loving what he was doing. Then he stopped sucking me and I sat down, he stood and stuck his cock through the hole. As if on auto pilot I leaned forward and started to suck his cock. It was my first time and I knew I loved having his cock in my mouth. I had been sucking him for a few minutes when I felt his cock swell and he came in my mouth. Squirt after squirt of it so much I had to swallow. I loved feeling it flowing up his cock as it expanded the underside of his cock and pressed against my tongue.

He finished thanked me and fixed his pants before leaving. As soon as he was gone another guy entered and didn't even sit, he just took out his cock and put it through the hole. His was I little longer, but not as thick, it was not quite hard and soon stiffened in my mouth. It grew a little longer, but not thicker. He went to the back of my mouth and started to go down my throat which caused me to gag. He told me to relax and try to take more each time. After several minutes I stopped gagging and he slid down my throat. Wow, that was wild and I loved the feeling. He asked me if he could come in my stall and I told him OK.

He came in and latched the door and told me to slide back on the seat so when I lean forward my mouth and throat will be more aligned. I did and he leaned on the door and I was able to let his cock slide right down my throat. He grabbed my head and started to fuck my throat. Every few seconds he let me take a breath. All too soon he held my head with his cock deep down my throat and I j knew he was shooting his cum. He fixed his pants and left.

I hadn't noticed, but another guy had entered the other stall and was standing with his cock through the hole. His was short and thick, about six inches, but the thickest so far and his balls were huge. It didn't take him long to cum and when he did, I thought I would drown in it there was so much. After he fixed his pants, he handed me a card and told me he staying at the Avery Hotel around the corner. He is in town every other month for two weeks and will be there for one more week and for me to drop by any day after five thirty.

I looked at the card and on the back was a phone number and room number. I stayed for about another forty-five minutes and sucked of six more guys. The last one returned the favor and sucked me off after feeding me his cum. I now had a new favorite place downtown an was looking forward to coming back soon. Two days later I started work on a construction site downtown. Every day after work I went to the State and would go straight down stairs to the bathroom. I would spend an hour sucking guys off before I would go to the Avery to suck off the guy, I learned was called Fitzy. I was getting good at sucking him and he would hold my head with his cock as far back in my mouth as it would go and when he would cum the force it would shoot straight down my throat.

It was about six months since the first time I was at the State. When I got to Fitzy's room, he had a woman with him. He told me: "Kid tonight you will have to eat my cum from Liz's cunt.'

I wonder if she was one of the hookers that turned trick in the area. He laid down and she got on top facing his feet. When he was near ready to cum, he told me to get between their legs and lick them both. I did as he asked and soon, he filled her with so much cum it was leaking out around his cock. When he pulled out of her I started sucking up his cum that was flowing out of her. Then I suck him clean they took a shower and when they were done, he had me suck him to get him hard. I thought he was going to fuck her again, instead when he was ready to cum, he had her give him a drinking glass and shot is load in it. She took a mouth full then passed it into my mouth and I was told to swallow. She repeated it emptying the glass.

When Fitzy went to the bathroom, I asked her: "You work in the area?"

She told me: "Yes, but not doing what you are thinking. I am a secretary at one of the companies he does business with. One of the other girls has been fucking him for a while and says he is a good fuck so, I decided to fuck him."

I said: "I hope I didn't offend you by what I was thinking."

She laughed and said: "Not at all, I fucked my boss to get the job and fucked him twice more for rises. Part of my job is to pleasure some of the more important clients."

Fitzy came back and asked her: "You staying or are you done for the night?"

She said: "I would love to stay, but my husband would be suspicious."

That bit of news shocked me, I didn't realize people did that, especially a woman cheating on her husband. It seemed from what she had told me, she must do it often.

Fitzy said: "How about both of you suck me off together before you go?"

She told him: "I don't think so, it will take you to long to cum this time."

He said: "How about I see you tomorrow night again?"

Her response was: "I can't be late getting home two nights in a row. How about when you come back to town we can get together again then."

With that she left and Fitzy told me he was going to go get something to eat and would see me another time. I dressed and headed out. As I approached the State, I saw a couple of guys I recognized from my job going in.

So, I decided to head home instead, when I got to Forest Hills, I needed to pee so, I went to the pay toilet at the end of the platform. Put in my dime and turned the knob to open the door. There were two guys in there with there cocks out watching each other jerk off. There were two stalls both without doors. The two guys were standing just outside each so I went into one and not to turn my back on them I sat down. The one nearest me turned towards me and pointed his cock at me. I finished peeing and leaned back and started stroking my cock. He took that as a sign and move to me putting his cock to my mouth.

The other one said: "Suck it for him, he shoots big loads."

I opened my mouth and started sucking the cock. The guy I was sucking moved to the side of the toilet so I turned my head to keep sucking him. I didn't know why he did that till the other one got down and started sucking my cock. I was the first to be ready to cum so I stopped sucking long enough to tell the guy sucking me I didn't want to cum till I sucked them both off. He stood up and move to the other side of the toilet. I moved to suck his cock and switched back and forth. The first guy tensed and filled my mouth with his cum. He then moved back to watch me sucking off the other guy, who soon filled my mouth with his load. The door opened and another guy came in, I got nervous because he had on a MBTA uniform.

He asked the two other guys: "How good is this cock sucker?"

The first told me: "He is great and he doesn't spit it out."

He unzipped his pants and fished out his cock and stepped in front of me and said: "Suck it."

I began to wonder if there were other bathrooms on the subway that I could suck cock. I would have to ask him after I finish sucking hm off. The three of them were talking and it seemed they all worked for the MBTA. When he came, I swallowed his load and the first guy was ready again and presented me with his cock, which I gladly sucked for him. Each had me suck a second load from them. The second guy had me stand and he sat down and started to suck me off. I asked the other two If there were other bath rooms like this on the system. Turned out there were two more and they are no longer avalible to use. But they told me this one was safe Wednesday and Friday nights after eight PM. So, I had another place to suck cock and fill my craving for cum.

One Saturday I went to the State and after I got in the place was empty. The movie was running, but there was nobody there. I went down to the bathroom and again there was no one. I went up to the ticket booth and asked if there was a reason nobody was there. He recognized me as I had sucked him off several times.

He told me: "The Pilgrim is showing a film that is very popular and it just opened yesterday. Everybody is going there."

I said: "That sucks I wish I had known that I would have stayed home."

He told me: "The Pilgrim does more business as it is bigger and you can suck cock there also and if you are daring you can do it at the back where the safety lights on the floor make so you can see. Of course, you will have an audience watching you."

That turned me on being watched, so I told him: "I will head over there, thanks for the information."

He replied: "Take this and give it to the woman in the ticket booth and she will give you a ticket for free."

I took the card he offered me and headed down the street to the Pilgrim. Handed the card to the woman in the booth and got my ticket. The lobby sloped up and on the right was a small concession stand. Just beyond was an escalator that was very old with wooden steps. Farther on was a door on the right with a sign over that said Ladies Room, beyond on the left was the entrance to the Men's Room. I glanced in and saw stairs leading down, continuing I came to the theater itself. I saw a narrow section of seats on the right and a wide section of seats in the middle. Farther over there was another smaller section of seats. I moved to the left a short way and leaned on the short wall just behind the last row of seats.

A few minutes later my eyes had adjusted and I saw others leaning on the same wall I was. I stepped back and looked over to the left and behind the short section of seats I saw a few guys. As I walked that way, I saw a guy on his knees sucking another guy while three more were watching. I saw one of them had his cock out and was hard. I waked up to him and started to stroke his cock before dropping to my knees and took his cock in my mouth. Soon the other two took out their cocks and move close to my face. I started going from cock to cock sucking them off. I lost track of how long it took, but I made each of them cum in my mouth. I needed to stand at that point and leaned against the wall behind the seats. I saw guys walk down the aisle to an opening on the left and go through it.

I asked one of the guys that was near me: "What is through that opening?"

He said: "It is very dark and you don't know who is sucking you or you are sucking. It also has stairs at the end that lead to the boxes on the sides of the upper levels and the balcony. I don't know what happens up there as I have never gone up that far."

I decided to check out the opening and headed there. He was right It was pitch black and I realized guys were against the right size and I needed to stay on the left. Hands reached out and felt my crotch so I took out my cock. Soon I stopped and reached to feel the guy's cock that was feeling my cock. It was big and he pulled me close and I knelt and stated to suck him off. I had no idea what he looked like, if he was White, Black, Latin, or Oriental. My only thought was his cock was big and I liked the way it felt in my mouth. He soon came and I swallowed, he moved away and another guy took his place. His cock wasn't as big, but I didn't care it was a cock and he would give me another load of cum.

I sucked three more after him and decided to check out the balcony and headed up the stairs. As I was approaching the first box of seats it was easier to see. The floor sloped up and I passed two more boxes. In one two guys were naked and in a sixty-nine. The next there was three guys all naked and one was sucking a cock while the third guy was fucking him in the ass. When I reached the balcony, I saw a woman with guys on each side of her. She was stroking both guys cocks, so I moved closer to get a better look.

I was shocked to see it was a guy dressed like a woman and he had a huge cock. One of the guys knelt on the floor and the one dressed as a woman feed him his cock. The third guy got behind the one in the woman's clothes and looked like he was going to fuck him in his ass. This place made the State seem tame and I wonders what else I would find. Going to the back of the balcony I found a corridor and offices, some had desks and chairs and others had pads on the floors. By the look they hadn't been used for business for some time.

I went back into the balcony and there were more people there most watching the three I first saw. Others jerking off watching the movie, so I went back down the way I came up. Now I was going to check out the men's room to see what happens there. The stairway down was wide and there were some guys standing at the sides as I went down. Most were smoking which I thought was illegal. At the bottom there was a good size room with benches and straight across I could see urinals on the right in the next room with stalls on the left. I headed that way and in an open stall I saw holes on both sides. The end stall opened and I guy came out zipping his pants. As I looked in, I saw a guy was looking through the hole in the partition. I went in and sat down and when he saw I didn't take down my pants he stood and stuck his cock through the hole. It was about seven inches and a decent thickness. I sucked him off and he left, but before I could leave another guy came in and stuck his cock through for me to suck.

It looked familiar for some reason so, I said: "Fitzy is that you.'

He said: "Jimmy is that you? When did you start coming here?"

I told him: "Today is my first time."

He asked me: "Do you want to go to the Avery or are you looking to stay so you can suck more cocks?"

I told him: "I was planning to stay another hour or so, but I will go to the Avery with you now or after I finish here."

He said: "Suck me off now and come to my room when you are done here. I'm coming over there for you to suck me off."

I did and it was much more comfortable to suck him off. We walked upstairs together and he left and I went to the left side behind the seats to suck some more cocks while other guys watched me. I did two guys, but then I wanted to back in the dark area that led to the stairs. There was something about not knowing what the guys I sucked looked like that was exciting for me. So, I went there and sucked off another six cocks. Though I couldn't see them the last guy thanked me and he sounded black. I had mixed feelings about that, if I had known ahead of time would I have still sucked him off. I realized by that time I was so turned on he could have been an animal and I probably would have sucked his cock.