Learning To Swing Both Ways Ch. 03

They all agreed to spend the night at the beach house and call into work sick on Monday morning. Jill and Nichole slept in one bed while Gary, Craig and Julian slept in the other. Sometime in the very early hours Gary was awakened by the bed moving. When his head cleared he realized that Craig was fucking Julian.

Craig was in the middle and he had his back to Gary as he fucked Julian from behind. Gary decided to get in on the action. His cock was hard so he moved it to Craig's ass and touched his anus with the head of his cock. Craig reached back and guided Gary's cock into his ass and then he resumed fucking Julian. Gary didn't have to move much since Craig's fucking motion caused his ass to slide back and forth on Gary's cock.

Gary felt Craig stiffen and he knew that Craig was cumming in Julian. Craig's asshole tightened around Gary's cock as he ejaculated into Julian's asshole. Then Craig relaxed but Gary was not done so he picked up the pace and fucked him with more urgency in search of his own orgasm. Julian reached back and took a hold of Gary's hand and brought it to his cock. Gary wrapped his hand around the erect uncut cock and jerked Julian off. Then Gary came and dumped a load in Craig's ass. Craig cooed and moaned when he felt the semen shoot into him. Julian then groaned as he came and Gary felt the ejaculation as cum shot from Julian's cock. Gary's cock eventually deflated and slipped from Craig's ass and they all fell back asleep.

THE MORNING AFTER

The next morning Gary woke up alone in bed. When he looked over at the other bed the guys were fucking the other's wife. Julian was fucking Jill and Craig was fucking Nichole. Gary went into the bathroom to take his morning piss and when he returned both women were greasing up their husband's assholes. Julian was on all fours in one bed and Nichole was applying the lube to her husband's asshole. In the other bed the same scene was repeated by Jill and Craig.

"Julian gets it first," Jill announced.

Gary was a little apprehensive about fucking Julian again. Gary was used to fucking Craig but fucking Julian seemed different. Gary looked at him again and he looked very feminine on all fours with his curvy ass awaiting Gary's cock. It was Gary's first fuck of the day so that helped the situation. Nichole took Gary's cock in her hands and stroked it with the lubricant. Then Gary got on the bed behind Julian and eased his lubricated cock into Julian's ass. As Gary was fucking Julian, Craig eased his big dick into Gary's ass. It didn't take Craig long to cum and he filled Gary's ass with a massive cum load. That triggered Gary's ejaculation and he filled Julian's ass to overflowing and cum actually gushed out when Gary removed his cock from Julian's ass.

"God that was like having a hose go off in my ass," Julian sighed and added, "There is no substitute for youth."

Craig was anxious for Gary to fuck him next and Gary had no trouble satisfying his desire. Jill put more lube on Gary's cock and then she guided it into her husband's ass. Gary lasted a little longer with Craig before he filled Craig's ass with his second load of the day. They finished off the morning with the two women each getting triple penetrated. Jill and Nichole loved having three cocks in them at the same time so they took advantage of the situation.

Nichole was first as she straddled her husband and lowered her pussy on his cock. Gary took her ass and Craig took her mouth. Nichole had multiple orgasms before the guys came again. She loved feeling cum shooting into her three holes. Then it was Jill's turn and after a brief rest she lowered her pussy onto Craig's cock as she took Julian in her mouth and Gary in her ass. Jill too had multiple orgasms before her holes were cum filled.

The five of them were sexually sated and drained. They all took showers and then ventured down to the beach for some more nude sun bathing. They packed food and drinks into a cooler and chilled out on the beach until it was time for Gary, Craig and Jill to leave for home. There were hugs, kisses and thanks all around before they packed the car and headed home. It was another three hour drive and they were all dead tired.

As Craig, Jill and Gary drove home, Gary thought about what had transpired in the past several days. It had been quite a weekend as Gary had fucked his second female ass in two days. He had now become comfortable fucking good looking asses male or female but he knew that he still liked cock. He also liked getting blow jobs from Jill but he was not ready to fuck any pussy yet. Gary felt that he had gone as far as he would ever go with a woman. Gary fell into a deep sleep as he had no idea of what was in store for him with his neighbors.

GARY'S FINAL BISEXUAL STEP

Gary became very close with Jill and Craig over the next several months and he loved having sex with them. They had done just about everything that a threesome could do except that Gary still had not fucked Jill's pussy. Jill never put any pressure on Gary to fuck her and Gary loved her for that. Gary had often fucked Jill in the ass while she was sucking or fucking Craig. Sometimes Craig fucked Gary in the ass while Gary fucked Jill in the ass or she sucked Gary's cock. They even had daisy chain sex once in awhile and Craig would eat Jill's pussy while Gary sucked Craig's cock and Jill sucked Gary's cock. Their variety and creativity was endless and Gary did not miss his gay friends.

So far Gary had avoided fucking Jill's pussy but his curiosity was getting the best of him. Could it really be that hard to do? Craig liked her pussy and yet he still liked Gary's ass and mouth. Gary finally decided that if the situation came up that he night just give fucking a pussy a try. Gary trusted Jill and if he couldn't handle the vaginal sex, he knew she would not ridicule him. It was a Saturday morning and Gary had stayed over with Craig and Jill. They had had another incredible Friday night of sex and they slept in on Saturday morning.

Gary had a morning erection and he looked over at Jill. Craig had already gotten up and was in the kitchen making coffee. Gary was thinking about fucking Jill when Jill beat him to it. She rolled over and spotted Gary's erection so she straddled him and lowered her pussy onto his cock. Gary was surprised and he was actually turned on by the warm moist feeling of her pussy. He found that he actually liked it as it was like nothing he ever felt before.

Jill was the perfect mate to break in Gary to vaginal sex. She rode his cock and did all the work. She let him enjoy the ride and Gary was pleased with her approach. Jill had a way of tightening her vaginal muscles and squeezing Gary's cock much the same way she used her anal muscles when he was in her ass. Jill also managed to keep her clit in contact with Gary's cock for her own pleasure.

Jill closed her eyes as she rode Gary's cock and Gary reached down and held onto her shapely firm ass. Gary was pleased that he was able to pleasure Jill this way. Jill continued to clench and unclench her vaginal muscles as she rode Gary's cock and then Gary felt his own orgasm building. He could feel the tension in his ball sac as his cock became even more rigid. This is it he thought, "I'm going to do it. I'm going to cum in her pussy."

Gary felt the surge of his cum shoot through his shaft and flood Jill's pussy. Stream after stream shot into Jill's womb as the barrage seemed endless. That was Jill's trigger and she cried out as she orgasmed. Her body shuddered and trembled as she was rocked with a massive orgasm. Jill's hips undulated rapidly as she got off on Gary's cock and then she collapsed on top of Gary. Jill cooed as her body began to recover from her mind blowing orgasm and Gary caressed her back and ass soothing her. Gary could feel the wetness surround his cock from their combined juices and he liked the warm wet calmness of the after sex.

"Good show you two! Congratulations Gary, you did it man. That is a big step and you are now officially a bi convert," Craig said standing by the bed.

Gary smiled as he realized that Craig was right. He had made it and now he would always enjoy all types of sex with both men and women. Jill rolled off of Gary and his cock slipped from her sopping wet pussy. Jill smiled at Gary and kissed him on the cheek as she took his wet cock in her hand and stroked it gently. They both rested in bed briefly before they finally got up and joined Craig in the kitchen for coffee. Gary was so pleased with himself that he beamed all morning as they enjoyed the coffee. He knew that he would be close to Craig and Jill forever.